Compendium of Organic Synthetic Methods
Compendium of Organic Synthetic Methods Volume 11 MICHAEL B. SMITH
DEPARTMENT OF CHEMISTRY THE UNIVERSITY OF CONNECTICUT STORRS, CONNECTICUT
A JOHN WILEY & SONS, INC., PUBLICATION
Cover illustration was adapted from “DisconnectBy the Numbers: A Beginner’s Guide to Synthesis” by M.B. Smith. Journal of Chemical Education, 1990,67,848-856.
Copyright 02003 by John Wiley & Sons, Inc. All rights reserved. Published by John Wiley & Sons, Inc., Hoboken, New Jersey. Published simultaneously in Canada. No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means, elcetronic, mechanical, photocopying, recording, scanning or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, (978) 750-8400, fax (978) 750-4470, or on the web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, h e . , 111 River Street, Hobokcn, NJ 07030, (201) 748-601 I , fax (201) 748-6008, e-mail:
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ISBN 0-471-25965-9 Printed in the United States of America. 10 9 8 7 6 5 4 3 2 1
CONTENTS PREFACE ABBREVIATIONS INDEX, MONOFUNCTIONAL COMPOUNDS INDEX, DIFUNCTIONAL COMPOUNDS INTRODUCTION 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16
PREPARATION OF ALKYNES PREPARATION OF ACID DERIVATIVES AND ANHYDRIDES PREPARATION OF ALCOHOLS PREPARATION OF ALDEHYDES PREPARATION OF ALKYLS, METHYLENES AND ARYLS PREPARATION OF AMIDES PREPARATION OF AMINES PREPARATION OF ESTERS PREPARATION OF ETHERS, EPOXIDES AND THIOETHERS PREPARATION OF HALIDES AND SULFONATES PREPARATION OF HYDRIDES PREPARATION OF KETONES PREPARATION OF NITRILES PREPARATION OF ALKENES PREPARATION OF OXIDES PREPARATION OF DIFUNCTIONAL COMPOUNDS
AUTHOR INDEX
vii ix xiii xiv xv 1 9 18 90 115 226 264 310 335 366 377 386 417 425 470 4.83
709
V
PREFACE
Since the original volume in this series by Ian and Shuyen Harrison, the goal of the Compendium of Organic Synthetic Methods was to facilitate the search for functional group transformations in the original literature of Organic Chemistry. In Volume 2, difunctional compounds were added and this compilation was continued by Louis Hegedus and Leroy Wade for Volume 3 of the series. Wade became the author for Volume 4 and continued with Volume 5. I began editing the series with Volume 6, where I introduced an author index for the first time and added a new chapter (Chapter 15, Oxides). Volume 7 introduced Sections 378 (Oxides - Alkynes) through Section 390 (Oxides - Oxides). This volume introduces Section 74G (Cyclobutanations). The Compendium is a handy desktop reference that will remain a valuable tool to the working Organic chemist, allowing a “quick check” of the literature. It also allows one to ”browse” for new reactions and transformations that may be of interest. The number of articles that comprise Organic literature is very large, and the Compendium is a focused and highly representative review of the literature and is offered in that context. Compendium of Organic Synthetic Methods, Volume 1 1 contains both functional group transformations and carbon-carbon bond forming reactions from the literature appearing in the years 1999, 2000 and 2001. The classification schemes used for Volumes 6-1 0 have been continued,- but one new section was added. Section 74G (Cyclobutanations) describes methods that produce cyclobutane rings. As in the past, difunctional compounds appear in Chapter 16. The experienced user of the Compendium will require no special instructions for the use of Volume 11. Author citations and the Author Index have been continued as in Volumes 6-10. Every effort has been made to keep the manuscript error free. Where there are errors, I take full responsibility. If there are questions or comments, the reader is encouraged to contact me directly at the address, phone, fax, or Email addresses given below. As I have throughout my writing career, I thank my wife Sarah and my son Steven, who have shown unfailing patience and devotion during this work. Steven Smith also prepared many of the drawings used in this volume, and I thank him for that contribution. I also thank Dr. Darla Henderson and Amy Romano, the editors for this volume. Michael B. Smith Department of Chemistry University of Connecticut 55 N. Eagleville Road Storrs, Connecticut 06269-3060 vii
viii
PREFACE
Voice phone: (860) 486-2881 F a : (860) 486-2981 Email:
[email protected] Homepage: http://orgchem.chem.uconn.edu/home/mbs-home. html Storrs, Connecticut April, 2003
ABBREVIATIONS
Ac acac AlBN aq.
Acetyl Acety lacetonate am-bis-i sobutyronitri le Aqueous 9-Borabicyclo[3.3.1 ]nonylboryl
9-BBN BER BINAP Brnim Bn
BZ
9-Borabicyclo[3.3. llnonane Borohydride exchange resin 2R.3S-2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl 1-butyl-3-methylimidaolium benzyl benzoyl
BOC
1-Butoxycarbonyl
bpy @PY) Bu CAM CAN cat.
2,2'-Bipyridyl n-Butyl Carboxamidomethyl Ceric ammonium nitrate cycloCatalytic
Cbz
Carbobenzyloxy
Chirald COD COT CP CSA CTAB
2S,3R-(+)-4-dimethylamino1,2-diphenyl-3-methylbutan-2-ol I ,5-Cyclooctadienyl 1,3,5-~yclooctatrienyl Cyclopentadienyl Camphorsulfonic acid cetyltrimethylammonium bromide C16H33NMe3+Br
CY(c-C&~i)
Cyclohexyl
C-
O C
DABCO dba DBE DBN DBU DCC DCE DCM DDY
0
Temperature in Degrees Centigrade 1,4-Diazabicylco[2.2.2]octane dibenzylidene acetone 1,2-Dibrornoethane 1,8-Diazabicyclo[5.4.O]undec-7-ene 1,5-Diazabicycl0[4.3 .O]non-5-ene
1,3-Dicyclohexylcarbodiimide
1,2-Dichloroethane dichloromethane 2,3-Dichloro-5,6-dicyano1,4-benzoquinone
+Ol8"
0 $OCH2Ph
BrCH2CH2Br
c-C~HI~-N=C=N-C-C~H II CICH2CH2C1 CHzC12
ix
ABBREVIATIONS
X
% de DEA DEAD Dibal-H Diphos (dppe) Diphos-4 (dppb) DMAP DMA DME
% Diasteromeric excess Diethylamine Diethylazodicarboxylate Diisobutylaluminum hydride 1,2-bis-(Dipheny1phosphino)ethane 1,4-bis-(Diphenylphosphino)butane 4-Dimethylaminopyridine Dimethylacetamide Dimethoxyethane
DMF
N,N‘-Dimethylfonnamide
h P
bis-[1,3-Di@-methoxypheny1)-1,3-propanedionato] dipivaloylmethanato 1,4-bis-(DiphenyIphosphino)butane Ph,P(CH,)dPPh, 1,2-bis-(Dipheny1phosphino)ethane PhZPCH,CH,PPh,
dPm dPPb dPPe dPPf dPPP dvb e% ee
EE Et EDA EDTA Emim FMN fod
FP
FVP Grubbs’ catalyst
MeOCH2CH20Me
il
H
N(CH3)Z
his-(Dipheny1phosphino)ferrocene 1,3-bis-(Diphenylphosphino)propane Ph,P(CH,),PPh, Divinylbenzene Electrolysis % Enantiomeric excess 1 -Ethoxyethoxy EtO(Me)CHOEthyl -CH2CH3 Ethy lenediamine HZNCH2CHzNHZ Ethylenediaminetetraacetic acid 1-ethyl-3-methylimidazolium Flavin mononucleotide fris-(6,6,7,7,8,8,8)-Heptafluoro-2,2-dimethyl-3,5-octanedionate Cyclopentadienyl-bis-carbonyliron Flash Vacuum Pyrolysis CI~(PC~,),RU=CHP~
n
MesGrubbs’ catalyst 11
HN(CH2CH3)2 EtO2C-N=NCOzEt (Me2CHCH2),AIH Ph,PCHZCHzPPh, Ph2P(CH&PPh,
NvN. Mes
I Ru = CHPh CI. I
“”
E Y 3
h hv
1 ,S-HD HMPA HMPT iPr LlCA (LIPCA) LDA LHMDS LTMP MABR
hour (hours) Irradiation with light 1,5-Hexadienyl Hexamethylphosphoramide (Me,N),P=O Hexamethylphosphorus triamide (Me2N)3P Isopropyl -CH(CH3)2 Lithium cyclohexylisopropylamide Lithium diisopropylamide LiN(iPr), Lithium hexamethyl disilazide LiN(SiMe,), Lithium 2,2,6,6-tetramethylpiperidide Methylaluminum bis-(4-bromo-2,6-di-tert-butylphenoxide)
ABBREVIATIONS MAD mCPBA Me MEM Mes MOM Ms MS MTM NAD NADP Napth NBD NBS NCS NIS Ni(R) NMP Oxone
bis-(2,6-di-r-butyl-4-methylphenoxy)methyl aluminum mefa-Chloroperoxybenzoic acid Methyl -CH3 P-Methoxyethoxymethyl MeOCH2CH20CH2Mesityl 2,4,6-tri-Me-C6H2 Methox ymethyl MeOCH,Methanesulfonyl CH3S02Molecular Sieves (3A or 4A) Methylthiomethyl CH3SCHZNicotinamide adenine dinucleotide Sodium triphosphopyridine nucleotide Naphthyl (C10H8) Norbornadiene N-Bromosuccinimide N-C hlorosuccinimide N-Iodosuccinimide Raney nickel N-Methyl-2-pyrrolidinone 2 KHSO,.KHS04.K,S04 Polymeric backbone
PCC PDC PEG
Pyridinium chlorochromate Pyridinium dichromate Polyethylene glycol
Ph
Phenyl
PhH PhMe Phth pic
Benzene Toluene Phthaloyl 2-Pyridinecarboxylate
Pip
Piperidino
PMP Pr
4-methoxypheny l n-Propyl
PY
Pyridine
quant. Red-A1 sBu sBuLi Siamyl TADDOL TASF TBAB TBAF TBAI TBDMS TBHP (1-BuOOH)
Quantitative yield [(MeOCH2CH20)2A1H2]Na sec-Butyl CH,CH&H(CH,) sec-Butyllithium CH3CH2CH(Li)CH3 Diisoamyl (CH&&HCH(CH,)a,a,a',a'-tetraaryl-4,5-dimethoxy1,3-dioxolane Iris-(Diethy1amino)sulfonium difluorotrimethyl silicate Tetrabutylammonium bromide n-Bu,N'BrTetrabutylammonium fluoride n-Bu,N'FTetrabutylammonium iodide n-Bu,N'It-Butyldimethylsilyl t-BuMe,Si f-Butylhydroperoxide Me3COOH
xi
xii t-Bu
TEBA TEMPO TFA TFAA Tf (OTf) THF THP TMEDA TMG TMS TMP TPAP To1 Tr TRIS Ts(Tos) x c
ABBRNIATIONS tert-Butyl Triethylbenzylammoniurn Tetramethylpiperdinyloxyfree radical Trifluoroacetic acid Trifluoroacetic anhydride Triflate Tetrahydrofuran Tetrahydropyran Tetramethylethylenediamine 1,1,3,3-Tetramethylguanidine Trimethylsilyl 2,2,6,6-Tetramethylpiperidine tetra-n-Propylammoniurn perruthenate Tolyl Trilyl Triisopropylphenylsulfonyl Tosyl = p-Toluenesulfonyl Chiral auxiliary
Me2NCH2CH2NMe2 -Si(CH3)3
VSP VOE
'was
EL LI
'Sd
I
N0113810Xd
I
861
6EP
ILP fIZ
OLP ilZ
OW 661
1Lt tlZ
LIP W1
LLE
LUC L91
is1
nLE CS1
6 s 891
EhE 691
WE LEI
LI)E 8fI
R9E 6CI
SEE CZ1
hEE PZI
OIE Lni
Pir 801
LIE 601
f6
SYZ
591 P6
9iz LL
OEZ 8L
6L
6EZ
E9 Oil 29
OZI
1Z1 C9
06 Lt
15 8P
86 6t
Ll
6
XI
ZE
01
81
01
61 61
Cf
hl Pf
,"
san!4r%uap P I P Jllh'xoqle3
I sl"ua~d'sl'WJIV
'apFqWv
I
I
I
I
562
550
695
6%
534
49Y
378
493
491
339 562
330
320
309
561
338
336 561
329 530
327 SIX
560
335
326
515
334 SM)
325 511
4')o
JYX
311 245
306 4x9
30s
316 497
315 4%
305 4x8
488
301
382 698
576
347
573
346
383 699
610
354 604
603
353
595
351
56%
344
592
350
343 565
342 565
702
384
630
625
340
359 624
(1x1
357
702
650,
365 644
642
364
Y
702
XIS
369 663
Y
/
703
387
669
372 667
I/ 704
388
689
/
/
389 705
70X
390
#' ,/
S e c t i o n s k a v y type Pages-light type
g I/
INDEX, DIFUNCTION AL COMPOUNDS
Blanks in the table correspond to sections for which no additional examples were found in the literature.
INTRODUCTION Relationship between Volume 11 and Previous Volumes. Compendium of Organic Synthetic Methods, Volume 7 7 presents 2781 examples of published reactions for the preparation of monofunctional compounds, updating the 13,050 in Volumes 1-10. Volume 11 contains 1212 examples of reactions that prepare difunctional compounds with various functional groups. Reviews have long been a feature of this series, and Volume 11 adds 41 pertinent reviews in the various sections. Chapters 1-14 continue as in Volumes 1-10, as does Chapter 15, introduced in Volume 6. Difunctional compounds appear in Chapter 16, as in Volumes 6-10. The sections on oxides as part of difunctional compounds, introduced in Volume 7, continues in Chapter 16 of Volumes 8-1 1 with Sections 378 (Oxides-Alkynes)through Section 390 (Oxides-Oxides). Following Chapter 16 is a complete alphabetical listing of all authors (last name, initials). The authors for each citation appear below the reaction. The principal author is indicated by underlininq (i.e., Kwon, T.W.; Smith, MB), as done previously in Volumes 7-10. Classification and Organization of Reactions Forming Monofunctional Compounds. Chemical transformations are classified according to the reacting functional group of the starting material and the functional group formed. Those reactions that give products with the same functional group form a chapter. The reactions in each chapter are further classified into sections on the basis of the functional group of the starting material. Within each section, reactions are loosely arranged in descending order of year cited (2001-1999), although an effort has been made to put similar reactions together when possible. Review articles are collected at the end of each appropriate section. The classification is unaffected by allylic, vinylic, or acetylenic unsaturation appearing in both starting material and product, or by increases or decreases in the length of carbon chains; for example, the reactions t-BuOH + t-BuCOOH, PhCH,OH + PhCOOH, and PhCH=CHCH20H + PhCH=CHCOOH would all be considered as preparations of carboxylic acids from alcohols. Conjugate reduction and alkylation of unsaturated ketones, aldehydes, esters, acids, and nitriles have been placed in Sections 74D and 74E (Alkyls from Alkenes), respectively. The terms hydrides, alkyls, and aryls classify compounds containing reacting hydrogens, alkyl groups, and aryl groups, respectively; for example, RCH2-H+ RCH,COOH (carboxylic acids from hydrides), RMe -+RCOOH (carboxylic acids from alkyls), RPh -+ RCOOH (carboxylic acids from aryls). Note the distinction between R2C0 + R2CH2(methylenes from ketones) and RCOR' RH (hydrides from ketones). Alkylations involving additions across double bonds are found in Section 74 (alkyls, methylenes, and aryls from alkenes). xv
xvi
INTRODUCTION
The following examples illustrate the classification of some potentially confusing cases: RCH=CHCOOH-+ RCH=CH2 -+ ArH + ArH -+ RCHO 4 RCH=CHCHO -+ RCHO -+ RzCH2 + RCH2COR -+ RCH=CH2 -+
RCH=CHz RCH=CHCOOH ArCOOH ArOAc RH RCH=CHp RCH3 R2CO RzCHCOR RCH&HS
RBr+HC=CH
RC=CR
-+
ROH + RCOOH -+ RCOOR RCH=CHCHO
-+
RCH=CHCN
-+
RCH2CH2CN
Hydrides from carboxylic acids Carboxylic acids from hydrides Carboxylic acids from hydrides Esters from hydrides Hydrides from aldehydes Hydrides from aldehydes Alkyls from aldehydes Ketones from methylenes Ketones from ketones Alkyls from alkenes (Hydrogenation of Alkenes) Acetylenes from halides; also acetylenes from acetylenes Esters from alcohols; also esters from carboxylic acids Alkyls from alkenes (Conjugate Reduction) Alkyls from alkenes (Conjugate Reduction)
How to Use the Book to Locate Examples of the Preparation of PJOtection of Monofunctional Compounds. Examples of the preparation of one functional group from another are found in the monofunctional index on p xiii, which lists the corresponding section and page. Sections that contain examples of the reactions of a functional group are found in the horizontal rows of this index. Section 1 gives examples of the reactions of acetylenes that form new acetylenes; Section 16 gives reactions of acetylenes that form carboxylic acids; and Section 31 gives reactions of acetylenes that form alcohols. Examples of alkylation, dealkylation, homologation, isomerization, and transposition are found in Sections 1, 17, 33, and so on, lying close to a diagonal of the index. These sections correspond to such topics as the preparation of acetylenes from acetylenes; carboxylic acids from carboxylic acids; and alcohols, thiols, and phenols from alcohols, thiols, and phenols. Alkylations that involve conjugate additions across a double bond are found in Section 74E (Alkyls, Methylenes, and Aryls from Alkenes). Examples of name reactions can be found by first considering the nature of the starting material and product. The Wittig reaction, for instance, is in Section 199 (Alkenes from Aldehydes) and Section 207 (Alkenes from Ketones). The aldol condensation can be found in the chapters on difunctional compounds in Section 324 (Alcohol, Thiol-Aldehyde) and in Section 330
INTRODUCTION
xvii
(Alcohol, Thiol-Ketone). Examples of the synthetically important alkene metathesis reaction are mostly found in Section 209 (Alkenes from Alkenes). Examples of the protection of acetylenes, carboxylic acids, alcohols, phenols, aldehydes, amides, amines, esters, ketones, and alkenes are also presented. Sections (designated with an A: 15A, 30A, etc.) are labeled “protecting group: reactions” and are located at the end of pertinent chapters. Some pairs of functional groups such as alcohol, ester; carboxylic acid, ester; amine, amide; and carboxylic acid, amide can be interconverted by simple reactions. When a member of these groups is the desired product or starting material, the other member should also be consulted in the text. The original literature must be used to determine the generality of reactions, although this is occasionally stated in the citation. This is only done in cases where such generality is stated clearly in the original citation. A reaction given in this book for a primary aliphatic substrate may also be applicable to tertiary or aromatic compounds. This book provides very limited experimental conditions or precautions and the reader is referred to the original literature before attempting a reaction. In no instance should a citation in this book be taken as a complete experimental procedure. Failure to refer to the original literature prior to beginning laboratory work could be hazardous. The original papers usually yield a further set of references to previous work. Papers that appear after those publications can usually be found by consulting Chemical Abstracts and the Science Citation Index. Classification and Organization of Reactions Forming Difunctional Compounds. This chapter considers all possible difunctional compounds formed from the groups acetylene, carboxylic acid, alcohol, thiol, aldehyde, amide, amine, ester, ether, epoxide, thioether, halide, ketone, nitrite, and alkene. Reactions that form difunctional compounds are classified into sections on the basis of two functional groups in the product that are pertinent to the reaction. The relative positions of the groups do not affect the classification. Thus preparations of 1,2-amino-alcohols, 1,3-amino-alcohols, and 1,4-amino-alcohols are included in a single section (Section 326, AlcoholAmine). Difunctional compounds that have an oxide as the second group are found in the appropriate section (Sections 278-290). The nitroketone product of oxidation of a nitroalcohol is found in Section 386 (KetoneOxide). Conversion of an oxide (such as nitro or a sulfone moiety) to another functional group is generally found in the “Miscellaneous” section of the sections concerning monofunctional compounds. Conversion of a nitroalkane to an amine, for example, is found in Section 105 (Amines from Miscellaneous Compounds). The following examples illustrate applications of this classification system:
INTRODUCTION
xviii
Difunctional Product RC=C-C=CR RCH(0H)COOH RCH=CHOMe RCHF, RCH(Br)CH,F RCH(OAc)CH,OH RCH(OH)CO,Me RCH=CHCH,CO,Me RCH=CHOAc RCH(OMe)CH2S02CH2CH20H RSOZCHZCHZOH
Section Title Acetylene-Acetylene Carboxylic acid-Alcohol Ether-Alkene Halide-Halide Halide-Halide Alcohol-Ester Alcohol-Ester Ester-Aikene Ester-Alkene Alcohol-Ether Alcohol-Oxide
How to Use the Book to Locate Examples of the Preparation of Difunctional Compounds. The difunctional index on p xiv gives the section and page corresponding to each difunctional product. Thus Section 327 (Alcohol, Thiol-Ester) contains examples of the preparation of hydroxyesters; Section 323 (Alcohol, Thiol-Alcohol, Thiol) contains examples of the preparation of diols. Some preparations of alkene and acetylenic compounds from alkene and acetylenic starting materials can, in principle, be classified in either the monofunctional or difunctional sections; for example, the transformation RCH=CHBr + RCH=CHCOOH could be considered as preparing carboxylic acids from halides (Section 25, monofunctional compounds) or preparing a carboxylic acid-alkene (Section 322, difunctional compounds). The choice usually depends on the focus of the particular paper where this reaction was found. In such cases both sections should be consulted. Reactions applicable to both aldehyde and ketone starting materials are in many cases illustrated by an example that uses only one of them. Likewise, many citations for reactions found in the Aldehyde-X sections, will include examples that could be placed in the Ketone-X section. Again, the choice is dictated by the paper where the reaction was found. Many literature preparations of difunctional compounds are extensions of the methods applicable to monofunctional compounds. As an example, the reaction RCI + ROH might be used for the preparation of diols from an appropriate dichloro compound. Such methods are difficult to categorize and may be found in either the monofunctionalor difunctional sections, depending on the focus of the original paper. The user should bear in mind that the pairs of functional groups alcohol, ester; carboxylic acids, ester; amine, amide; and carboxylic acid, amide can be interconverted by simple reactions. Compounds of the type RCH(OAc)CH,OAc (ester-ester) would thus be of interest to anyone preparing the diol RCH(OH)CH,OH (alcohol-alcohol).
INTRODUCTlON
xix
Sources of Literature Citations. I thought it would be useful for a reader
of this Compendium to see those journals that contain the most new synthetic methodology. The accompanying graph shows that Tetrahedron Letters, Organic Letters, and Journal of Organic Chemistry account for roughly 46% of all the citations in Volume 11. In past volumes, Tetrahedron Letters and Journal of Organic Chemistry have accounted for 50430% of all citations. The advent of the new journal Organic Letters, the consolidation of several European journals into the European Journal of Organic Chemistry, and the apparent expansion of synthetic methodology relative to the last two volumes probably accounts for the new relationship of the three cited journals. This book was not edited to favor one journal, section or type of
Citation Sources,Volume 11 950
900 850
800 7.50 700 650 600 550
g 500 .z u
a. .
.*
450 400
350
300 250 200 1 so 100 50 0
Journal
xx
INTRODUCTION
article over another. Undoubtedly, my own personal preferences are part of the selection, but I believe that this compilation is an accurate representation of new synthetic methods that appear in the literature for this period. Therefore, I believe the accompanying graph reflects those journals where new synthetic methodology is located. I should point out that the category “16 other journals” includes: Helvetica Chimica Acta, Journal of Heterocyclic Chemistry, Pure and Applied Chemistry, Journal of Chemical Research (S), Monatshefte fur Chemie, Russian Journal of Organic Chemistv, Acta Chemica Scandinavica, Israel Journal of Chemistry, Chemistry, A European Journal, Canadian Journal of Chemistry, Chemistry Letters, Chemical Reviews, Bulletin of the Chemical Society of Japan, Organic Preparations and Procedures International, Accounts of Chemical Research, Heterocycles, and the Australian Journal of Chemistry In addition, 6 more journals were examined but no references were recorded.
Cornpendium of 0rganic Synthetic Methods
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 1 PREPARATION OF ALKYNES
SECTION 1: ALKYNES FROM ALKYNES
+ 20% 1,4diphenyl-
19-hutadiyne Chow. 14.-F.; Wan, C.-W.; Low, K.-H.; Yeung, Y.-Y. J. Org. Chenz., 200Z, 66, 1910.
-
1. B uLi , KOt-Bu , THF hexane, -78°C -25°C
7
2. 2 eqMeI , .--43"C -+ rt
\
7
Kowalik. .I.Tolhert, ; L.M. J. Org. Chem., 2001, 66, 3229.
Ph
= 5% Pd,(dbah*CHCl3,
10% C U I ,rt 2 eq NaOMe , MeOWMeCN, rt , 3 h
S.-K;Kyu, 11.-C.; Lee. S.-14. Syntlz. Corrtrrzun., 200Z, 31, 1059.
74%
2
Section 1
Compendium of Organic Synthetic Methods, Vol 11
=
Ph
-
PhZI'BFL ,DME;JH,O , rt NaHC03, 30 min
hP-P
85%
S.-&; Yoon, S.-K.; Kim, Y.-M. Org. k t f . , 2001, 3, 2697.
&me.
=
Ph,Sb(OAc), , 10%CuI, 5 h
* 7 P 5% Pd2(dba),-CHCI3, MeCN 50°C Kanp.;Ryu, H.-C.;Hong, Y.-T. J . Chem. Soc., Perkin Trans. I , 2001, 736. ph
PhSe
SiMe3
=
CF3SiMe3, Bu4NF
CH(OEt),
+ Me3Si
=
Yoshimatsu.; Kuribayashi, M. J. Chem. SOC.,Perkin Trans. I , 2001, 1256. Me02C-
3. PhI, cat Pd(PPh3)4 -78°C -t 23"C, 3 h Org. Left.,2001, 3, 31 1 1 .
Anastasia, L.;
-
C6H13
*
MeOzC
88%
=
PhI, 2 eq TBAF, 2%CuI w
1% PdCl2(F'Ph3)2 ,THF, rt
-
Et3SiH , 1% Ir4(CO)12
GH13
* P h =
12% PPh3 . . Shimizu, R.; p u c h i k a u. Tetruhedron k t t . , 2000, 41, 907, PhBr , 3 %Pd(PhCN)2C12 6% P(t-BU), , 2% CUI
P h =
-Ph
= 93 %
=
SiEt3
Ph
1.2eq i-Pr2NH,It dbxane Fu. G . C . Org. Lett., 2000, 2 , 1729. Hundertmark, T.; Littke, A.F.; Buchwaid..L.: I
P h =
O
o
M
Ph
98 %
J'vlori. A.; Shimada, T.; Kondo, T.; Sekiguchi, A. Synlett, 2001, 649. Ph
81%
CH(OEt),
TIIF, 0°C
1. LDA ,THF 2. ZnBr, ,T I I F , -78°C
h
96%
94%
e , TIIF, 60°C
* P h - e O M e 0.5%Pdz(dba), , 2% PPh3 TBAF , 6 h Mon.;Kawashima. J.; Shimada, T.; Suguro, M.; Hirabayashi, K.; Nishihara, Y. Org. k t t . , 2000, 2, 2935.
\ /
83%
3
Alkynes from Alkynes
Section 1
Pd-CuI-PhP hdKF-A1203
94%
Kahalka.G.W,; Wang, L.; Namboodiri, V.; Pagni, R.M. Tetruhedron Lett., 2000, 41, 5151.
- -
BuLi, B(0i-Pr), , DME-THF + C6Hl, p-Tol-Br , 3 % Pd(PPh3)4
=
p-Tol
98% Kang, S.; Jang, T.-S.; Keum, G.; Kang, S.B.; Han, S.-Y.; K i m . O r g . Lett., 2000, 2, 3615. TMSCF3, cat CSF, THF
Ts- N
0.5 h quant
. . M.; IIoshino, 0. Tetruhedron, 2000, 56, 8657, 8661. w.
F h =
0.5% Pd2(dba), , NEt, , THF
-
F ' h - O A c
\ /
0.5% P(t-Buh , rt , 2 0 h
.p
Bohm, V.P.W.;
//
W.
>99%
. Eur. J. Org. Chem., 2000, 3619. Me0
\
2.5% Pd2(dba), , 20% CuI 20% 2,6-di-r-Bu-phenol DMF , i-PrzNEt , -20°C
MeOzC Nakamura, K.; Okuho, H.; Yamacuch i. M. Synlett, 1999, 549. K#&4-&03,
pentane +
\ =
flt,2h Cadclick. S.; Murtaugh, L.; Weacing, R. Tetruhedron Lett., 1999, 40, 3655
52%
Compendium of Organic Synthetic Methods, Vol 11
4
Section 4
0
6% (r-BuO),W C C t -Bu
bluene ,80"C
/
*
69%
Furstner.;Guth, 0.;Rumho, A.; Seidel, G. .IAm. .
Chem. SOC., 1999, 121, 11108.
SECTION 2: ALKYNES FROM ACID DERIVATIVES NO ADDITIONAL EXAMPLES
SECTION 3: ALKYNES FROM ALCOHOLS AND THIOLS NO ADDITIONAL EXAMPLES
SECTION 4: ALKYNES FROM ALDEHYDES 1. CC13COOH, (TJl,COC-Na+
DMF ,35"C
*
2. TsCl , TENDABCO ,DCM ,25"C 3.4.5 eq MeLi , TI-IF , -10°C 9SX91X94% 4.&O+ Wanp.; Campagna, S.; Yang, K.; Xu, G.; Pierce, M.E.; Fortunak, J.M.; Confalone, P.N. J. Org. Chem., 2000, 65, 1889. 1. Ph3PCHBr2 Br , THF r-BuOK ,rt 2. r-BuOK
*
B
Michel. P.: Gennet. D.: Rassat, A. Tetruhedron Lett., 1999, 40, 8575.
G
C
C
H 66%
5
Alkynes from Halides
Section 10
1. LDA ,TIIF ; DCM , --78"C 2. TsCl , TEA, E M , 25°C
4. 3.3.5 II,O+ MeLi ,TIIF, -10°C *
Wane.; Yin, J.; Campagna, S.; Pesti, J.A.; Fortunak, SECTION 5:
e
x
9
3
x
9
1
%
J.M. J. Org. Chem., 1999, 64, 6918.
ALKYNES FROM ALKYLS, METHYLENES AND ARYLS NO ADDITIONAL EXAMPLES
SECTION 6:
ALKYNES FROM AMIDES NO ADDITIONAL EXAMPLES
ALKYNES FROM AMINES
SECTION 7:
NO ADDITIONAL EXAMPLES
ALKYNES FROM ESTERS
SECTION 8:
NO ADDITIONAL EXAMPLES
SECTION 9:
ALKYNES FROM ETHERS, EPOXIDES AND THIOETHERS NO ADDITIONAL EXAMPLES
SECTION 10:
+d
ALKYNES FROM HALIDES AND SULFONATES
OTf
t-Bu Ilalhes, IJ.; Bertus, P.;
Bu-aC-SiMe, ,TBAF cat Pd(PPh3)d , a t AgI 3 HZO, 21 h
t-Bu Tetruhedron LRtt., 2001, 42, 8641.
Section 10
Compendium of Organic Synthetic Methods, Vol 11
6
PhI, PdCuI-PPh3 ,neat
-SiMe3
P h = P h
*
KF-Al20, ,microwaves ,2.5 mm 90%
Kahalka. G.W,; Wang, L.; Pagni, R.M. Tetruhedron, 2001, 57, 8017.
,Pd(PPh3hCh
-SiMe3
G
L
\ I
EtzNH , DMF , microwaves 120°C , 5 min
I
S
i
M
A. J. Org. Chem., 2001, 66, 4165. 1. PhI, cat Pd(PPh,)4
Bu3Sn-
2. Merrifield resin , NaI
w
= 93%
Blomgren, P.A. Org. Lett., 2001, 3, 1869.
;-
=
Ph
SiMe,O€I
PhI, T H F , TBAF, 60°C
5% Pd(PPh3)4,2.5 h
* P h = 97%
Yang, S.H.; Lee, P.H. Tetruhedron Lett., 200Z, 42, 4833.
;&-
/
S ~ M0.5 Q AgC03 I o , 5 o% PM ~ ( OeA C ) ~i / P PP~ ~
Ph
PhI
O
Bu$rlCi ,THF, 65°C , 2 h
Koseki, Y.; Omino, K.; Anzai, S.; &ga&aL Li[-:B
B(Omh)3]
*
ph
Ph
M
e 92%
Tetruhedron Lett., 2000, 41, 2377.
5% Ptl(PPh3)4, 5% CUI 15h, DMF Oh. C&; Jung, S.H. Tetruhedron Lett., 2000, 41, 8513.
PB -r
REVIEW: “Formationof Acetylenes by Ring-Opening of 1,1,2-Trihalocyclopropanes,” Svdnes. L.K.Eur. J. Org. Chern., 2000, 3511.
94%
q
Section 14
7
Alkynes from Alkenes
SECTION 11:
ALKYNES FROM HYDRIDES
For examples of the reaction RC-CH (Alkyne- Alkyne).
4
RCEC-CECRI, see section 300
NO ADDITIONAL EXAMPLES
SECTION 12:
ALKYNES FROM KETONES 1. NaH ; TfzO 2. TFA
C ,()0B 2-tu
PhOI ,c 14
3. KzCO3, acetone, 4 h
reflux Ramarao, C. Chem. Commun., 1999, 1113.
SECTION 13:
-
WH,C),
72~68%
ALKYNES FROM NITRILES
x X=H 69% X=Me 73% Yoo. B.-WL;Lee, S.-J.; Choi, K.-H.; Keum, S.-R.; KO, J.-J.; Choi, K.4.; Kim, J.-H. Tetruhedron Lett., 2001, 42, 7287.
SECTION 14:
ALKYNES FROM ALKENES NO ADDITIONAL EXAMPLES
=
8
Compendium of Organic Synthetic Methods, Vol 11
SECTION 15:
Grasa, G.A.;
Ph
AIXYNES FROM MISCELLANEOUS COMPOUNDS
d'(oH)z ,Pdddba)3
=
-
Bu
Section 15A
SMe
Cu(I) -thiophene-2carhoxylate THF ,50°C
Bu
S.P. Org. Lett., 2001, 3, 119. 1 . BuLi, TIIF 2.PhCHO
S02Ph
*
-ph
3. Ac@ 4. LDA ,THF ,-78°C + rt 74% Orita, A,; Yoshioka, N.; Struwe, P.; Braier, A,; Beckmann, A,; O t e r a . C h e m . Eur. J., 1999, 5 , 1355.
SECTION 15A:
PROTECTION OF ALKYNES NO ADDITIONAL EXAMPLES
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 2 PREPARATION OF ACID DERIVATIVES
SECTION 16:
P h = Li, J.; Li, G.;
SECTION 17:
ACID DERIVATIVES FROM ALKYNES
c o , 3% 1 1 2 0 , cat PdCl2 2 eq CuC12, clioxane , rt , 9 h
*
ho 98%
0
0 Tetruhedron Lett., 2001, 42, 6923.
ACID DERIVATIVES FROM ACID DERIVATIVES HO ,C
I
in hexane + 12-c-4 Brun, E.M.; Gil, S . ; Yarra, M. Synlett., 2002, 156.
cqrr
(84
:
16) 85%
(30
:
70) 74d.
PPh3, C C I F N , DCM
NEt3,rt,1 h Kim.; Jang, D.O. Synth. Contrnun., 2001, 31, 395.
c1
89%
10
Compendium of Organic Synthetic Methods, Vol 11
C02H
Section 19
1 . 2 . 2 9 sec-BuLi, THF , -78°C 2. Me1 3. H2O
80% (90: 10) Mortier, J.; Vaultier, M.; Plunian, B.; Sinbandhit, S. Can. J. Chem. 1999, 77, 98.
SECTION 18:
c5H 11CH2OH
ACID DERIVATIVES FROM ALCOHOLS AND THIOLS Na2W04*2H 2 0 , Bu4NHS04
*
30% aq H z 0 2 ,microwaves, 20 mm Cukasiewicz, M. Synlett, 2000, 143.
C5HllC02H
75%
m;
PhCHZOH
1. TEMPO, MeCN ,35"C yodium phosphate buffer
PhCOzH 98% 2. NaCIO2 ,dilute bleach Zbao. M,;Li, J.; Mano, E.; Song, Z.; Tschaen, D.M.; Grahowski, E.J.J.; Reider, P.J. J. Org. Chem., 1999, 64, 2564. NaIO4 , R~Cl-pH20,EtOAc
* Ph-C02H MLCN/H~O Prashad. M.;Lu,Y.; Kim,H.-Y.; Hu, B.; Repic, 0.;Blacklock, T.J. Synth. Conzmun., 1999, 2Y, 2937. PhwoH
93%
SECTION 19: ACID DERIVATIVES FROM ALDEHYDES PhCHO
~ ~ i t H 2 ,0HCOOH 2
*
Pha2H
96%
rt,15h . . Balicki. B, Synth. Conimun.,2001, 31, 2195. PhCHO
N- hrnmophthali~nide-IIg(OAc),
Anjum, A,; & i u v a s.. P. Chem. Lett., 2001, 900.
; .H-
urea-H202 ,aq NaOH , 1 h P hCHO * Newhold, A.J. Tetrukdron Ldt., 2001, 42, 6607.
*
PhCOOII
PhCO,H
94%
94%
Section 20
11
Acids from Alkyls
H202-SeO2,
THF
reflux, 5 h
99%
Wcjjtowicz, H.; Brzpzcz, M.; Kloc, K.; Mlochowski, J. Tetruhedron, 2001, 57, 9743.
73% Sato, K.; Hytdo, M.; Takagi, J.; Aoki, M.; Noyor L& Tetruhedron k t t . , 2000, 41, 1439. bmnate exchange m i n
* PhCOOH octane, =flux Chetri, A.B.; Kalita, B.; Das. P.J, Synth. Commun.,2000, 30, 3317. PhCHO
€124
PhCXO
, cat S e 9 , T H F
*
PhCooH
*
PhC02H
reflux, 2.5 h Synth. Conmun., 2000, 30, 4425. PhCIIO
O2 , A1203,micluwaves
Reddy, P.P.; &ddv. P.S.N. Synth. Commun.,1999, 29, 2949. Reddy, D.S.;
SECTION 20:
97%
58%
ACID DERIVATIVES FROM ALKYLS, METHYLENES AND ARYLS C O , V q a c a L h ,K2S208 CF3CO0I-I
CH't
88%
+
CH,COOH
93%
Taniguchi, Y.; Hayashida, T.; Shihasaki, H.; Piao, D.; Kitamura, T.; Yamaji, T.; Org. Lxtt., 1999, 1, 557. Ph-- CH3 ,
'
0.5 clo, ,35eq €I@,
Ph-H
MtCN,rt, 1 h Org. LEtt., 1999, 1, 2129. NaOCI,MeCN,rt,I h
02N-@.
. .
* Synth. Commun., 1999, 29 , 2211.
85%
CO,H 98%
12
Section 23
Compendium of Organic Synthetic Methods, Vol 11
SECTION 21: ACID DERIVATIVES FROM AMIDES PhCON HNMe,
2 qPhI(OH)OTs,
H20
t
91%
wuts. P . m ; Gohle, M.P. Org. Lett., 2000, 2, 2139.
+&
ji
Ph
250°C, 4 atm
/
NH2
*
30 min
Ph O H' 99%
0
+ phthalimide
TerrohedronLeft.,2000, 41, 3855.
SECTION 22: ACID DERIVATIVES FROM AMINES NO ADDITIONAL EXAMPLES
SECTION 23: ACID DERIVATIVES FROM ESTERS
($
co2i-pr
AlC!, , MeNO,
H 2oc$(
10"C,ld
92%
N HC02i- Fr Chee, G.-L. Synlett, 200Z, 1593. C e l C02t-Bu
N€IC02i- Pr
SiO, , toluene ~ f l u x7, h
* C
Buck, M.;
1. BuLi , THF
\0 C/ O
2
H
74%
R.W, Tetruhedron k t t . , 2001, 42, 5163. =-UB
I
t
B-CloH21
2. CloHzlI, reflux, 8 h Tetmhedron k t t . , 2001, 42, 5825.
75%
Section 25
13
Acids from Halides
-
1. ZnBr,, DCM , 1d
P hCnzt-Bu
PhCO,H 2. HzO , 2 h Wu.Y-0,; Limhurg, D.C.; Wilkinson, D.E.; Vaal, M.J.; Hamilton, G.S. Tetruhedron Lett., 2000, 41, 2847.
86%
irzo
so,,
* PhCHzCQH microwaves Ranu.; Dutta, P.; Sarkar, A. Synth. Conzmun., 2000, 30, 4167. PhCHZC02Me
PhSH ,KZCD3,NMP
PhC0,Me
+
PhCO,II
190"C, 10 min Tetruhedron, 1999,55, 9595.
Shar~na,L.; Nayak, M.K.;
92%
quant
Other reactions useful for the hydrolysis of esters may be found in Section 30A (Protection of Carboxylic Acids).
SECTION 24:
ACID DERIVATIVES FROM ETHERS, EPOXIDES AND THIOETHERS
A0
P 11
Bi(II)mandelate ,0, , DMSO +
R'yc%Er , 80°C ,4.5 h OH
Coin, C.; Le Boisselier, V.;Favier, I.; Posbel, M.;
SECTION 25:
PhCHZCl
PhC02kI
<
58%
Eur. J. Org. Chem., 2001, 735.
ACID DERIVATIVES FROM HALIDES AND SULFONATES 30% IIzOz,cat Na,W04-2 H,O Me(C4H17)3N+HS04-, MS 4A
-
PhCOOH
83%
t-Bu 90°C
aFeng, Y.-S. J. Org. Chem., 2001, 66, 3235.
\ /
Itoh. A.: Kodarna, T.; Inagaki, S.;
mesoporous silica, hv acetone , 2 0 h '
* t
-
Org. Lett., 2000, 2, 2455.
\B ./
0
co,ir 86%
14
Compendium of Organic Synthetic Methods, Vol 11
10% [RhCl(cod)], , 1 atm C O
ph-7 Br
*
Section 27
Ph-l CO2H 93%
5% KI , HCOOEt ,60°C,18 h Giroux.;Nadeau, C.; Han, Y. Tetruhedron Lett., 2000, 41, 7601.
SECTION 26: ACID DERIVATIVES FROM HYDRIDES
&.
0
SO&,
cat Vqacac), , 1 d 46% conversion
Y.: Matsunaka, K.; Sakaguchi, S. J. Am. Chem. Soc., 2000, 122, 7390.
(0.34
:
Asadullah, M.; Taniguchi, Y.; Kitainura, T.;
0.1 0.24) 58% Tetruhedron Lett., 1999, 40, 8867.
SECTION 27: ACID DERIVATIVES FROM KETONES aq Oxone, NaHC03 ~
Lee.
Ph r
.
w
d Ph MeCN ,pH <5 .W,; Grega, K.C. J. Org. Chem., 2001, 66, 1523.
L
[hydroxy (2,4dinitrobenzcnesulfonyloxy)iodo] benzene MeCN ,reflux, 1 h
Ph J.C.; Choi, J.-H.; Lee, Y.C. Synlett, 2001, 1563. K O H D M F , 68"C, 12 h
*
-
PhCOOH
PhCO2II
97%
75%
PhCOOH
47%
Tetruhedron Lett., 1999, 40, 6077. Zabjek, A,; sA.
A
RQO,, 70% TBIIP, 5 h
Ph Gurunath, S . ; Sudal ai. A. Synlctt, 1999, 559.
PhCOOH
71%
Section 29
Acids from Alkenes
0
1. t-B uOH , 3 0 % aq H202 2.30% H202 for eachof 4* d
15
@C02H
60%
3.10% '14 KZCO, Giurg, M.; Mlochowski, J. Synth. Commun., 1999, 29, 2281.
A
PhCHO ,hexane, BF3(gas)
-
Bu-€02H reflux, 1.5 h Bu Bu Kahalka. G.W,; Li, N.-S.; Tejedor, D.; Malladi, R.R.; Gao, X.; Tmtman, S. Synth. Contmun., 1999, 29, 2783.
-
67%
SECTION 28: ACID DERIVATIVES FROM NITRILES NO ADDITIONAL EXAMPLES
SECTION 29: ACID DERIVATIVES FROM ALKENES 1 atm C O , H 2 0 , H2S04
[Rh(C0)41+ ,fi * 3('02H68% Xu. 0,;Nakatani, H.; Souma, Y. J. Org. Chem., 2000, 65, 1540. p a 2 , 96%
\ -
3<'"'"
Er2so,
* 1 atmCO X U & ; Fujiwara, M.; Tanaka, M.; Souma, Y. J. Org. Chem., 2000, 65,8105.
A
1. (R0)2BH, Rh(d);BF4-,
BINAP
Ph
0
Chen, A; Ken, L.;
2. LiCIIC12 3. NaC102
.
--
p 2 H
*
n
Ph
c:::
J. Org. Chem., 1999, 64, 9704.
supported hetero-pol yacid 1-120, , 1d
70%
*
9 9 ~ 8 7 %(93% ee, R)
90%
Brooks, C.D.; Huang, L.-c.; McCaiTon, M.; Johnstone. R.A.W, Chem. Commun., 1999, 37.
16
Compendium of Organic Synthetic Methods, Vol 11
4
PdClZ(PPh3h, COM20 * /I,,H TsOI1, LiCl Ph Org. Lett., 1999, I , 459.
Ph
Seayad, A,; Jayasree, S.;
Section 30
91 %
REVIEWS: "Palladium-Catalysed Reppe Carbonylation,"
SECTION 30:
Chem. Rev., 2001, 101,3435.
ACID DERIVATIVES FROM MISCELLANEOUS COMPOUNDS
-w
SnBq
t-BuOH , 5 0 T
VO(OCHZCF,)Ch/36 h 100% 60% 19% V q O C IIZCF3>c h/3 h Hiram T.; Morimoto, C.; Takada, T.; Sakurai, H. Tetruhedron Lett., 2001, 42, 1961.
PhCH=N-OI 1
*
PhC02H
99% 30% HzOz, THF , reflux, 10 h Synth. Contmun., 2001, 31, 3151. Giurg, M.; Said, S.B.; Syper, L.; m c h o w &iJ
REVIEWS: "Carboxylic Acids and Esters,"
J. Chem. Soc., Perkin Trans. 1, 1999, 3537
eJ
Section 30A
SECTION 30A:
Protection of Acids
17
PROTECTION OF CARBOXYLIC ACID DERIVATIVES
NaH,DMF,rt
~
92% o-Wu. M&; Regueiro-Ken, A.; St. Laurent, D.K.; Carroll, T.M.; Balasuhramanian, B.N. Tetruhedron Lett., 200Z, 42, 8593.
THF, rt Wang, M.F.; Golding, B.T.; Potter. &A. Synth. Commun., 2000, 30, 4197. Other reactions useful for the protection of carboxylic acids are included in Section 107 (Esters from Carboxylic Acids and Acid Halides) and Section 23 (Carboxylic Acids from Esters).
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 3 PREPARATION OF ALCOHOLS
SECTION 31: ALCOHOLS AND THIOLS FROM ALKYNES NO ADDITIONAL EXAMPLES
SECTION 32:
ALCOHOLS AND THIOLS FROM ACID DERIVATIVES OH MeCHO
Y
O0 z
H phenylpyruvate decarboxylase 0 76% (87% ee) Tetmhedron Asymm., 2001, 12, 571.
Guo, Z.; Goswami, A.; Nandur, V.B.;
BnEt,N+BF; , reflux, DCM
B uCO~ZI
Ndrdslmhdn.; , , . . Swarnalnkshmi, S.; Balakumar, R. Synth.
-
PhS02C1
>
70%
Commun., 2000, 30, 941.
3.5 q Zn + Me$iCI2, 3 eq DMA 1.2DCE,75"Ct 15 h
DMA = dimethylacetamide IJchiro, 11.; Kohavashi. S, TetruhetEronZxtt., 1999, 40,3179.
Ph
CO,H
BuCH~OH
-
PhSH
95 %
c1 1.
a
&(" N A N
,DME*fl
N-methylmorpholine , 3 h 2. NaBH4, H20 , 0°C
*
-OH Ph
Falorni.;Porcheddu, A.; Taddei, M. Tetmhedron Lett., 1999, 40,4395.
92%
Section 34A
19
Alcohols from Aldehydes
SECTION 33:
ALCOHOLS AND THIOLS FROM ALCOHOL AND THIOLS
1. haeSO$l,
i
DCM ,25"t
2. LiA1H4, THF
&
OH
C,H ,,CH,CH,OH
47%
OH
Benedetti. F.; Norhedo, S. Tetruhedron Lett., 2000, 41, 10071.
" F A A , MeCN h ydroslfide -supported polymer re sin
+
C$,,CH2CH2SH 85%
Sadavarte, V.S.; Uppalla, L.S. Chem. Lett., 2000, 1304.
;-
SECTION 34: ALCOHOLS AND THIOLS FROM ALDEHYDES The following reaction types are included in this section: A. Reductions of Aldehydes to Alcohols B. Alkylation of Aldehydes, forming Alcohols. Coupling of Aldehydes to form Diols is found in Section 323 (Alcohol-Alcohol). 1. CF3SQH-THF t PhCH,OH 83% 2. Z-BUNHZ-BH~ Lukln.;Yang, C.X.; Bellettini, J.R.; Narayanan, B.A.; Leanna, M.R.; Rasmussen, M. Synlett, 1999, 59.
PhCH2(OMe)2
SECTION 34A: PhCHO
REDUCTIONS OF ALDEHYDES TO ALCOHOLS Ph3PBu+BH4-, DCM ,rt
b
PhCH,OII
&ygmur. A .R.;Mallakpour, S.E. Synth. Commun., 2001, 31, 1177. PhCHO
Yu,H.;
PhB(0II)L ,Bu3Sn€I,DCM rt , 4 h
Synth. Cornmun. 2001, 31, 2719.
t
94%
PhCHzOH 88% (15% without PhB(OH)2)
20
Section 34A
Compendium of Organic Synthetic Methods, Vol 11
3 eq HC02Na, H@
CHO
58%
34OoC-35O0C B r y a n . T.A.; Jennings, J.M.; Gibson, J.M. Tetruhedron Lett., 2000, 41, 3523. Mg-FeCb , aq DMF
P hCI I 0
LPhCHzOH rt,25h Swami. s.s.; Desai, D.G.; Bhosale, D.G. Synth. Commun., 2000, 30,3097.
[emim] PF, ,B B u 3 , 16 h
PhCHO
92%
PhCH,OH
L-
quant
ionic liquid medium
Kabalka.;Malladi, R.R. Chem. Commun., 2000, 2191. PhCHO Liu, W.-y.; Xu, Q.-h.;
NaBH4, SiOz ,rt , 10 min
LPhCH20H Org. Prep. Proceed. Int., 2000, 32, 596.
Bu3SnH ,MeOH
-CHO Ph ~.
L-
P
h
96%
M
O
reflux quant
Kamiura, K.; Wada. M. Tetruhedron Lett., 1999, 40, 9059. PhCHO Bagnell, L.;
i-PiOH ,225"C, 1 d
*
PhCHzOH
92%
t
PhCH,OII
90%
Chem. Commun., 1999, 281.
IKHO , NaOH, 25 sec
PhCHO
microwaves Thakuria, J.A.; Baruah, M.; Sandhu. J.S. Chem. Lett., I999, 995. Zn , BnNE4C1, MeOH
-
PhmzOH reflux,4 h Kardile, G.B.; Desai, D.G.; Swami. S.S. Synth. Commun., I999, 29, 2129. PhCHO
P hCI I 0
1 . SnC12-2 IIzO, Mg , THF 2. H Z 0
Bordoloi.;Sharnia, R.P.;
PhCHzOH
Chakraborty, V. Synth. Commun., 1999, 2Y, 2501.
90%
90%
H
Section 34B
21
Alcohols from Aldehydes
ALKYLATION OF ALDEHYDES, FORMING ALCOHOLS
SECTION 34R:
ASYMMETRIC ALKYLATIONS Ti(Oi-Pr), , TIIF , AlEt3 PhCHO
* tE' chiral sulfonated amino Ph alcohol ligand , 0°C You, 1 . 4 . ; Hsieh, S.-11.; Fau. €I.-M. Chem. Comrnun., 2001, 1546. 1.
/ASiMe, , cat TiF, , 0°C
kHO
OTIF'S
S-BINOL, DCM
2. aq HF ,MeCN
Bode, J.W.; Gauthier Jr., D.R.;
PhCIIO
-
4
*
Lt
EtzZn, his-amino-alcohol , 0°C toluene
=-
Ph
0.65 PhzZn , Et,Zn, 10°C toluene, chiral Re catalyst
97% (98% ee) J.P.; Raabe, G.
Angew. Chem. Int. Ed., 2001, 40, 1488.
E@,
Kj' 93% (84% ee)
Bolm.;Kesselgruher, M.; Hermanns, N.; Hildehrand,
P hCI I 0
OTIPS 011
Chem. Commun., 2001, 2560.
Ooi, T.; Saito, A,; Maru oka. K . Chem. Lett., 2001, 1108.
a-
98% (96% ee)
toluene-hexane ,rt
5% 2-azanorbornyl+xazolidine catalyst
Nakano.;Okuyama, Y.; Iwasa, K.; -Heterocycles, &SnBu3
PhCHO chirai phosphine-AgOTf , TI-IF
84% (88% ee)
u
'ph
L =L Ph
72% (77% ee)
2001, 54, 411.
Ph
88% (96% ee)
Yanagisawa, A.; Nakashima, €1.; Nakatsuka, Y.; Ishiba, A.; Bull. Chcvn. Soc. Jpn., 2001, 74, 1129.
22
Compendium of Organic Synthetic Methods, Vol 11
QH -
-
EtzZn ,hexane, toluene ,rt
P hCHO
15%chiral amino-alcohol , 1 d*
2 eq EtzZn , PhMehexane ,0°C 2% his(oxazo1me) ligand , 4 5 h
Schinnerl, M.; Seitz, M.; Kaiser, A.;
97% (72% ee)
ph&
Liu, D.-X.; Zhang, L.-C.; Wang, Q.; Da, C.-S.; Xin, Z.-Q.; A.S.C. Org. Lett., 200Z. 3, 2733.
PhCHO
Section 34B
Wane.;Choi, M.C.K.;
*
Chan,
96% (93% ee)
Ph Et Org. L.ett., 2001, 3, 4259.
Sp--L48% (>99%ee,S)
PhCIIO
10%TSA*HzO12O"C, 20 h Ph Ohga, M.; Nakamoto, H.; Matushara, T.; Hussain, I.; Kataoka, K. J. Am. Chem. SOC., 2001, 123, 9168. CIIO
NO, 68% (76%ee) Sakthivel, K.; Notz, W.; Bui, T.; Barhas III, C.F. J. Am. Chem. SOC.,200Z, 123, 5260.
P hCI I 0
ZnEtz, norephedrine thiol ligand
98% (99% e e , R)
toluene * PhEt' Jimeno, C.; Moyano, A.; PericBs. M.A.; Riera, A. Synlett, 2001, 1155. m S n B u 3
PhCHO Kii, S.; &uuhJ.
-L
, CHzClz, 0°C
95% (99% ee ,S)
Ti(IV) catalyst, 2h Ph Tetruhedron k t t . , 2001, 42, 1935. 2 eq E t2Zn
PhCHO
chiral amino-alcohol Hermsen, P.J.; Cremers, J.G.O.; Thijs, L.;
*
JEt 99% ( 9 2 % e e , S ) Ph TetruhedronLett. 2001, 42, 4243.
Section 34B
23
Alcohols from Aldehydes
, SiC14,6 h
-SnBu3
QH -
-
.-
P hCHO 5% chiralphosphoramide , -78°C
85% (79% ee)
-L -L
Denmark.;Wynn, T. J. Am. Chem. Soc., 2001, 123, 6199. EtJn, toluene, 0°C
PhCtIO
cat bis-f5-amino-alcohol
Xu, Q.; Wang, H.;
92% (95% ee S)
v.; Chan, A.S.C.; Yang, T.-k. Tetruhedron Lett., 2001, 42, 6171.
-
T i - c h i r al diol , hexane
P hCHO
Ph
97% (91% ee) Et,Zn , 0°C rt Ph Yang, X.-w.; Shen, 1.-h.; Da, C.-s.; Wang, H.-s.; Su, W.; Liu, D.-x.; M(ane.; Choi, M.C.K.; Chan, A.S.C. Tetruhedron Lett., 2001, 42, 6573.
PhCIIO
Et&,
c h i d amino-alcohol
-
QH
*
hexane ,0°C PhAEt ' Tetruhedron, 2001, 57, 4825.
Ohga, T.; Umeda, S.;
97%ee,R
Et,Zn, 10%(C,F,,CI12CH,),C-OII
90% (83% ee ,R )
P hCI I 0 toluene-hexane , rt ,20 h
. ,
; -
* PhtE'
Okumura, K.; Ohgo, Y. Tetruhedron, 2001, 57, 5565. Et,Zn ,toluene , 0°C
\ /
15% c h i d pyrrolidinylmethanol derivative
Zhao.; I,i,
X.-G.; Wang, X.-R. Tetruhedron Asymm., 2001, 12, 399.
P hCI I 0
B
~
~
O
,Zn A , qC NII,Cl
22°C
Lomhardo.;Girotti, R.;
Morganti, S.; m
i n
*
96% (93% e e , SS)
Jp
Ph
OAc 90% (65:35 syn:anti) .i .. C. Chem. Commun., 2001, 2310.
Compendium of Organic Synthetic Methods, Vol 11
24
PhCHO
EL,&, 5% sulfinyl ferrocene ligand toluene, rt
Section 34B
Ipri\/
c
80%(88%ee)
Ph Chem. Commun., 2001, 2026. ~~
Priego, J.; Manchefio, O.G.; Cahrera, S.;
PhCHO
Et,Zn, toluene, hexane
96% (83% e e , R) 20% chiral quinoline 0°C- It Xu, Q.; Wang, G.; Pdn.; Chan, A.S.C. Tetmhedron Asymm., 2001, 12, 381. &Br
YH
, S b , 0.5M HCl , H20
eL
Li, L.-H.; Chan, T.H. Cun. J. Chem., 2001, 79, 1536.
PhCHO
Et,Zn , toluene, 0°C , 7 8 h
cat iron tricarhonyl-amino alcohols
ph
67% (89% e e , 5') Okanioto, K.; Kimachi, T.; Ihuka, T.; Takemoto. Y . Tetruhedron Asymm., 2001, 12, 463.
I'hCHO
Et,Zn ,Ti(0i-Pr), , bluene chiral amine, MS 4 A , -30°C
i"
*
phA Et
1. CICH2CICH, MII, TMSCl
P hCI I 0
10% Cdsalen) , MeCN
-
2. fl+ , THF Bandini, M.; ; Mechiorre, P.; Tino, R.; Tetmhedron Asymm., 2001, 12, 1063.
P hCI I 0
2 eq ZnEt2 , toluene, rt
quant (59% ee)
2 ,
Lake, F.; &lohere. C , Tetruhedron Asymm., 2001, 12, 755.
58% (56% ee)
Ph
ptl,
99% (87% ee , S) cat binaphthylazepine lipillid Ph Superchi, S.; Mecca, T.; Giorgio, E.; Tetruhedron Asymm., 2001, 12, 1235.
PhCHO
2.2 eq EtJn, toluene, -30°C chiral amino-alcohol ligand
-1
Et Ph Cohb, A.J.A.; Marson. C.M. Tetmhedron Asymm., 2001, 12, 1547.
99% (64% ee)
PhCHO
25
Alcohols from Aldehydes
Section 34B
/IEt
2.2 eq EtzZn , toluene , 0°C , 7 h
* Ph
dendritic BINOL-Ti catalyst
99% (84% ee)
Fan.; Liu, G.-H.; Chen, X.-M.; Deng, G.-J.; Chan, A.S.C. Tetruhedron Asynim., 2001, 12, 1559.
PhCHO
Et,Zn , toluene, 43 h
* J 10% chiral ferrocenylph amino-alcohol ligand Bastin, S.; Aghossou-Niedercom, F.; Brucard, J.; E%&LL, Tctrulicdron A.syni.nz.2001, 12, 2395.
quant (83% ee)
t
JEt
1. Et,Zn, P-cillholine esterligand
PhCHO
E
toluene, rt
2. H30+ Ph a u . H.J.; Zhao, B.T.; Zuo, G.-Y.; Pittman Jr., C.U.; Dai. W.M.: Hao. X.J, Tctruhedron Asymin. 2001, 12, 2613. Et,Zn, Ti(Oi-Pr), , DCM , rt , 1 h
74% (39% ee)
quant (96% ee , R)
oCHo PhCHO
chiral sulfonated amino-alcohol * PhE t' You, J.-S.; Shao, M.-Y.; Gau. 1L-K Tetruhedron Asymm., 2001, 12, 2971.
BH
E M , 20"C, 19 h
/
PhNMe, , chiral Al compkx
63% (43% ee) Gothelf, A.S.; Hansen, T.; J!Argensen, K.A. J. Chem. SOC., Perkin Trans. 1, 2001, 854.
P hCHO Sato, I.; Saito, T.;
PhCAO
Et+,
neat
chiral amino-alcohol
-1 Ph
Et
99% (87% ee)
Chem. Commun., 2000, 2471. 2 eq Et2Zn , toluene ,rt , 1 d
5% chirdl amine hicyclo[2.2.l]heptme alcohol *
tE' Ph
99% (94%ee) Hanya, N.; Mino, T.; Sakamoto, M.;Euj&iJl Tetruhedron Lett., 2000, 41, 4587.
26
Compendium of Organic Synthetic Methods, Vol 11
Et,Zn ,5% chiral piperidine hexane, 0°C
PhCHO
Section 34B
88% (24% ee, S)
*EthP'
Shl.;Jiang, J.-K.; Feng, Y.-S. Tetrahedron Asymm., 2000, 11, 4923. g\/SnBu3
PhCHO
, aq EtOH , 4 O " C
*
(9-tolyl-BINAP , AgN03, 14 h 93% (79% ee)
Loh. T.-P.; Zhou, J.-R. Tetruhedron Lett., 2000, 41, 5261. 20% bis-naphthyl , hexane Et
Ti(Oi-Pr), ,45"C perfluom(m thyldecalm) Tian, Y.;
Ph
99% (54% ee)
Tetrahedron L.ett., 2000, 41, 8813.
=
CHO
1. allyldialkoxytitanium complex ether, -78°C
2. HzO
Bouzhouz.;Pradaux, F.; cossV.;Ferroud, C.; Falguibres, A.
53% (96% ee)
Tetruhedron Lett., 2000, 41, 8877. 1) PhMezSi
QIi -
---
BOW),
MeCHO 2) I I 2 0 2 , pH 6 huffer 3) Na$03, 0"
*
80% (93%ee)
SiMqPh h u s h . W.R; Pinchuk, A.N.; Micalizio, G.C. Tetruhedron Lett., 2000, 41, 9413.
P hCIiO
Et,Zn ,toluene, rt , 12 h
*L
chiral carbohydrate derivative Ph U.B.T.; Chun, Y.S.; Yang, W.K. Tetruhedron Asymm., 2000, 11, 2149.
83% (90% ee)
l.ZnPh@nEt, 5%chiral femcenyl catalyst 2. workup
92% (95% ee) Bolm. C.; Hermanns, N.; Hildebrand, J.P.; Muiiiz, K. Angew. Chern. Int. Ed., 2000, 39, 3465.
Section 34B
27
Alcohols from Aldehydes
AlEti ,THF, 12 h
PhIIO
OH
I
r
Ti(IV)-TADDOL ate complex Ph Lu, J.-F.; YOU,J.-S.; - Tetruhedron Asymm., 2000, 11, 2531. i-Pr,Zn , a morpholino-xylofuranose
C&,,CHO
-1
88% (96%ee)
toluene, 0°C , 8 h
i-Pr
C6H13
Yang, W.K.; W L B.T. Tetruhedron Asynzm., 2000, 11, 2947. 2 eq Et2Zn , 5 %chirdl amino-alcohol
PhCHO
* tE'
toluene , rt Hanyu, N.;Aoki, T.; Mino, T.; Sakarnoto, M.; Tetruhedron Asymm., 2000, 11, 2911.
PhCHO
. .
99% (93%ee)
Ph
Et2Zn , 6 %hydioxy-henzylamine
93% (89%ee)
toluene, rt Tetruhedron Asymm., 2000, 11, 3361.
Ph
/IEt
Et2Zn, cat chiral amino-alcohol
PhCHO
94%(84%ee)
*
92% (77%ee) Ph Wu. Y.; Yun, H.; Wu, Y.; Ding, K.; Zhou, Y. Tetruhedron Asymm., 2000, 11, 3543.
PhCI 1 0 ;-
toluenehexane , 5 h
polymer-hound BINOL, catalyst Et,Zn, Ti(0i-Pr), ,DCM ,0°C
* QEI
---
*
Ph Shin, Y.-J. Tetruhedron Left., 2000, 41, 9515.
92% (95%ee)
Et,Zn , toluenelhexane , 5 h C
I
O
C
H
O cat amino-alcohol
97% (91.5% ee) Yun, H..; JVu. Y.;Wu, Y.; Ding, K.; Zhou, Y. Tetruhedron Lett., 2000, 41, 10263. PhCHO
2 eq EtzZn, cat chiral amino-alcohol toluene , 2 h
Hanyu, N.;Aoki, T.; Mino, T.; Sakamoto, M.; Tetruhedron Asynim., 2000, 11, 4121.
99% (93%ee) tE' Ph
Compendium of Organic Synthetic Methods, Vol 11
28
Section 34B
,Ti(0i-F'r)d
/ m S n B u 3
Jhthyl , toluene
25°C , 2 0 h
Doucet.
L;Santelli, M. Tetruhedron Asymm., 2000, 11, 4163. Et,Zn, rt , 1 d
PhCIlO
- *
cat hrdged chiral amino-alcohol Arroyo, N.; Haslinger, U.; Mereiter, K.;
'
tE' 84% (96% ee) Ph TetruhedronAsymm., 2000, 11, 4207.
1 . Et,Zn , cat thiazolidine derivative PhCHO
2. H+
?I I
J ,
99%(89%ee)
Ph Et Meng, Q.; Li, Y.; He, Y.; Gum. Y,Tetruhedron Asymm., 2000, 11, 4255. PhCIIO Shen, X.; Guo, H.;
PhCHO
EtzZn, BINOLcatalyst , DCM
* tE' Ti(Oi-h)4, -7O"C, hexane Ph Terruhedron Asymm., 2000, 11, 4321. Et,Zn , c h i d amino-alcohol
* Ph .I. Org. Chem., 2000, 65, 2108.
toluene , 1 8 T , 20 min
Palco, M.R.; Caheza, I.;
*
96% (91% ee)
98% (97% ee , S)
3 eq E tzZn ,TIIF , -20°C AcO
-L
1 . .A ; Adiuns, N.D. J. Org. Chem., 1999, 64, 5201. PhCIlO
Br
,Ce(OTf)4-xHz0
75% (95 : 5 anti:syn) 90% ee
chiral ligand Ph L h . T.-P-; Zhou, J.-R. Tetruheclron Lett., Z999, 40, 9115.
90% (92% ee ,R)
Section 34B
Alcohols from Aldehydes
29
* L E*!%
Et2Zn, toluene , 0°C , 3 h PhCHO
Ph
HO-
quant (97% ee ,S)
Reddy, K.S.; Sol& L.; Moyano, A.;
; Riera, A. J. Org. Chern., 1999, 64, 3969.
,M&H, -20°C
&si(oMeh
; 80% (94% ee) catR-Tolyl-BINAP-AgF , 4 h ph Yanagisawa, A.; Kageyama, H.; Nakatsuka, Y.; Asakawa, K.; Matsumoto, Y.; Angew. Chem., Int. Ed., 1999, 38, 3701.
PhCIiO
p
EtzZn , 2 % chiral amino-alcohol PhCHO
t
0°C ,toluene, 5 h Ph €ho. F3.T.; Chun, Y.S. Synth. Cnmmun., 1999, 29, 521.
M
e
\ 0/
0 CHO
PhzZn, toluene, -3O"C, 1 d cat (chiral diary1 carbonate
+ ZnEt2) 84% (93% ee)
Huang W.-S.; &-L. J. Org. Chern., 1999, 64, 4222. 2 eq Et2Zn , toluene/DCM, rt PhCHO
polymer bound aziridinylmethanol
ten Holte, P.; Wijgergans, J.-P.; Thijs, L.; Br ,T€IF/hexane
P hCHO
88% (83% ee ,R)
In , h c h o n i i e
L,
91%(96%ee,S) Ph
-L Ph
Org. Lett., 1999, I, 1095.
73% (72% ee ,S)
x~~
Loh. T.-P.; Zhou, J.-R.; Yin, Z. Org. L t t . , 1999, 1, 1855. 2 eq Et2-Zn
PhCHO 5%
+&lH
N I Trt Gadhwal, S.; Baruah, M.;
Ph *
L, Ph
Synlett, 1999, 1573.
90%(99%ee)
30
Compendium of Organic Synthetic Methods, Vol 11
P hCI I 0
&SnBu3
bL
, DCM ,rt
5% (S, S-(PhebOX)F&Clz(HzO) Motoyama, Y.; Narusawa, H.; Nishiv
Section 34B
Ph
88% (61% ee) Chem. Comnzun., 1999, 131.
(84 >950/0ee
16 dr) 55%
'
Barrett. A.G.M,; Braddock, D.C.; de Koning, P.D. Chem. Conmsun., 1999, 459.
Iltl,
Et,Zn , hexane ,0°C -t rt
PhCHO
10% chirdl pyrmlidine
* Ph 97% (97% ee) Yang, X.; Shen, J.; Da, C.; Wanp.; Choi, M.C.K.; Yang, L.; Wong, K.-y. Tetruhedron Asynzm., 1999, 10, 133. chiral amino alcohoL-2 BuLi
PhCHO Schon, M.;
THF , -78°C , 1h &gf&
PhCfIO
*I Ph
Tetruhedron Asymm., 1999, 10, 169.
Bu
17% (71% ee)
BuLi ,c h i d bis-amide, -1 16°C
* PhBu' 72% ee Arvidsson, P.I.; Davidsson, 0 ;nilmenson. G. Tetruhedron Asymm., 1999, 10, 527. DEE/DMM
C N - B n
P hCI I 0
Et,Zn , hexane , 0°C
5% c h i d azetidine
*
99% (92% ee)
tE' Ph
Shi.;Jiang, J.-K. Tetruhedron Asymm., 1999, ZO, 1673. PhCI-IO
Et,Zn ,0°C , 3 0 h
81% (>99% ee)
chiral disulfide ligand * PhtE' Braes.; Appelt, H.R.; Schneider, P.H.; Sliveira, C.C.; Wessjohann, L.A. Tetruhedron Asymm., 1999, 10, 1737.
Section 34B
Alcohols from Aldehydes
31
2 eq E tzZn , 2 d , toluene ,0°C
PhCHO
Ph tE' 5% chird pyridyl alcohol Kanrr.; Kim, H.Y.; Kim, J.H. Tetruhedron Asymm., 1999, 10, 2523.
JEt
Et,Zn , toluene, 0°C P hCHO
82% (90% ee)
86% (95% ee)
*
chiral2,2'-bipyridyl diol Ph Kwonr. H .-J,.; Lee, W.-S. Tetruhedrnn Asynim., 1999, 10, 3791.
PhCHO
Et,Zn , toluene , -30°C
92% (78% ee)
10% camphor-derived
EPhxEt 1,4-amino-alc~hol K d b u k J L ; Ferencic, M.; Giirtner, P. Tetruhedron Asynim., 1999, 10, 3969.
LEt
2.2 eq EtzZn, toluene ,0°C
PhCEIO
91% (88% ee) cat Cinchona alkaloid *Ph Lee, S.H.; Im, D.S.; Cheon B. C.S.; Chung, B.Y.Heterocycles, 1999, 51, 1913. CHO
lOeq-SiC13
,HMPA
chiral DCM, amide-78°C , HMPA , 7 d * +(76%ee) Iseki. K.; Mizuno, S.; Kuroki, Y.; Kohayashi, Y. Tetrulzeclron, 1999, 55, 977.
PhCHO
Et,Zn ,toluene, 0°C ,70h
2% polymer-supported ephedrine Ph 85% (83% ee) derivative Sung, D.W.L.; Hodge.;Stratford, P.W. J. Chem. Soc., Perkin Truns. 1, 1999, 1463
NON-ASYMMETRIC ALKYLATIONS 1. 3 eq BuL-LiDMAE hexane ,-60°C. 1 h
*
~
2. t-BuCHO, THF -GO"C, 1 h Choppin, S.; Gros, P.; Fort. Y. Eur. J. Org. Chem., 2001, 603.
z
-
B
u 69%
OH
Compendium of Organic Synthetic Methods, Vol 11
32
PhCIIO
& Ph,
-SIB%
Section 34B
P
+
h
y
cat Bu4NBr-Ph12, H 2 0
OH
2-allyltin gives 9 3 7 syntunti
OH
(90 10) 80% Shihata, I.; Yoshimura, N.; Yabu, M.; Baha. & Eur. J. Org. Chem., 2001, 3207.
CTH15CHO
1. I
w
B
r ,In
+
2. Phl, cat Pd(PPh3)4,LiCl Hirashita, T.; Yarnamura, H.; Kawai, M.;
CH ' 15?Fb
43%
OH
Chent. Conttitun., 2001, 387.
PhCHO , aq THF ,70"C , 7 2 h 3 eq SnCJ , cat Pd(PhCN),C12
Uph 0
Ph\s//
*
65%
Tetruhedron Asymm. 2001, 12, 1625.
Mh-quez, F.; Lleharia, A.;
3. P-TsOH ,PhH ,80"C
22%
Soai.;Konishi, T.; Shihata, T. Heterocycles, 1999, 51, 1421.
m
B
r
,p-sno
CRO a t PtCl2(PPh3k , 4TIIF Sinha, P.;
PhCHO Pourhaix, C.; .
Chenz. Cornmun., 2001, 1798.
c1
1
H>-i , DME F , H2O Td ~
3% R ~ ( x x ) ( C O ) ~ ,3% dppf ,80"C Ph F.: ' Org. Lett., 2001, 3, 803.
p-To1
62%
PhCHO
33
Alcohols from Aldehydes
Section 34B
YHJC
awe,
1. IO%Cr-salen , 10%,Mn,TMSCl d e n , MeCN
Ph
2. H* ,TIIF
C1
40%
ph
Bandini, M.; $lg&UL ; Melchiorre, P.; Morganti, S.; Umani-Ronchi.. Org. Irtt., 2001, 3, 1153.
5%
PhBr ,NiBr,*hipy PhCHO
t
ph
65%
Maz
Ph DMF ,e-,FdCr/Ni anode Durandetti. M.;N6dClec, J.-Y.; PBrichon, J. Org. Lett., 2001, 3, 2073.
-
Et,Zn, cat Ni(acac)z, rt
Zn ,hexane/TEIF, 15 min
Shihata, K.; Kimura, M.; Shimuzu, M.; Tarnaru. Y. Org. Lztt., 2001, 3, 2181.
Top;\\
SnCl, ,-78°C
CHO
-
IIH $
PMP 0
60%
N\
PMP
Alcaide.;Pardo, C.; Rodriguez-Ranera, C.; Rodriguez-Vicente, A. Org. k t t . , 2001, 3, 4205.
mso, B(C,FS), - 7 8 c CHzClz ,ether 9
81% vinylogous Mukaiyama aldol Tetruhedron Lett., 2001, 42, 1269. Chirstmann, M.;
Section 34B
Compendium of Organic Synthetic Methods, Vol 11
34
OH PhCHO, C C l ,
Ph-m3
lt,THF
Barma, D.K.; Baati, R.; Valleix, A.; .-
A
C... F,
91% U Org. Lett., 2001, 3, 4237.
1. Li ,DTBB , t-BuCHO THF ,-78°C
COzMe
2. p ~ ; q $ t t b ; ~ ~ ; ( p H 7) t-Bu 3. MeOH ,pTsOH ,20"C overnight Pastor, I.M.; Yus. M_ Tetrahedron Lett., 2001, 42, 1029. m S i M e 3
58%
, Sc(OTf)3
PhCHO
t
90%
CH2Clz,rt , 5 h Ph Yadav..;Suhba Reddy, B.V.; Srihari, P. Synlerr, 2001, 673. 1. TMSOTf, CI12CI, -78°C SiMqPh
. .
2. aq NaOH
-0 HoJ%,o,
Melllll~~~
81% (83: 17 c k t r a n s ) Iwanami, T.; Yamamoto, A.; fio. Y, Synlett, 2001, 1042.
COzEt
Et02CCIf0, 1% Pd(MeCN)ZClz
*
D C M , r t , 18h Hao, J.; Taktak, S.; Aikawa, K.; Yusa, Y.; Hatano, M.;
Mdan$J-
96% H Synlett, 2001, 1443.
PhCIIO ,SnClz, NCS CHzClz, -60°C , 3 9 h
L
Mdsuvdma.; , , . Saeki, K.; Horiguchi, S.; Kurusu, Y. Synlett, 2001, 1802.
P 74%
h
35
Alcohols from Aldehydes
Section 34B
OBn
1. Cp&rC& ,BuLi
c-
2. PhCHO
96% (86: 14 antixyn) Tetruhedron Lett., 2001, 42, 1677.
85%
Takernoto.; Anzai, M.; Yanada, R.; Fujii, N.; Ohno, H.; Ihuka, T. Tetruhedron Lett., 2001, 42, 1725.
1. PhCHO
OEt
C02Et
BIIj*THF, CH2C12,-78°C
Hillier, M.C.;
4
a 0
q+ 88%
2. (Et0)2POCI12C02Et, 2 eq NaH THF,-78"C + rt . Tetruhedron Lett., 2001, 42, 5145.
NhC15, B I $ether, ~ I -78°C W
*
or1
Ph
(c-C6111I)2BCI,hexane , rt
1) 63%
-1
Ph 2,6-lutidine, 12 h G.W,; Wu, 2.;Ju, Y. Tetruhedron Lett., 2001, 57, 1663. PhBr , cat Pd(OAc),/PPh3
Bu-CH0
OH
Ph
(3 Andrade.; Azevedo, N.R.Tetruhedron Lett., 2001, 42, 6473. PhCI-I0
87~59%
Cs2C03 ,o-xylene , 3 h 1GOY! Terao, Y.; Kametani, Y.; Wakui, 11.; Satoh, T.; Miura. M.; Nomura, M. Tctruhedron, 2001, 57, 5967.
75%
c-GH11
Compendium of Organic Synthetic Methods, Vol 11
36
Section 3 4 3
Jdoh. T.-P,; Tan, K.-T.; Yang, J.-Y.; Xiang, C.-L. Tetruhedron Lett., 2001, 42, 8701
1
Nocentini, T. Tetruhedron Lett., 2001, 42, 4557.
1
&Bf
PhCHO
, Mn*
*
THF-hexane Kakiya, H.; Nishimae, S.; Shinokubo, H.; C
O
PhCHO
NH4C1
Ph
Tetruhedron, 2001, 57, 2365.
60%
Et,Zn ,hexane ,0°C
91%(97% ee)
chiral leucine derivative
Kawana
82%
i 1. PhCIIO, 2 eq TiCl(Oi-Pr)3 acetophenone ,20"C
L
2.
Pastor, I.M.;
Tetruhedron, 2001, 57, 8807.
Ph
u; Mitsuie, T.; Miki, M.; Sakamoto, T.; Nishitani, K. Tetrahedron, 2000, 56, 175. )2BC1 ,NEt3
PhCI-IO
*
2. H,O
P
an h
b
75%
G.W.; Wu, Z.; Trotman, S.E.; Gao, X. Org. Lett., 2000, 2, 255.
2
PhB(OH)2, DME/II20 ,50"C Rh(Xac)(we)z, P(t-Bu),
Ueda, M.;
J. Org. Chem., 2000, 65, 4450.
*
99%
Section 34B
Alcohols from Aldehydes
C1
37
PhCHO ,DMF ,Clclz
c1
Baati, R.;
.
1
'
73% (56:44) J. Org. Chpnz., 2000, 65, 1235.
JJPh
5% Pd(OAc), ,PhOII , 10% PPh3, rt
-
PhCHO, 2 eq BEt, , hexane/THF, 27 h Kimura, M.; Tomizawa, T.; IIorino, Y.; Tanaka, S.; m Tetruhedron Lttt., 2000, 41, 3627. SiCI,
Phff I 0
u
or4
I
, DMF, 0.2 h I
5% AgOTf
Eu-
78%
. Y.
; Voigtlinder, D. Synthesis, 2000, 959.
BF,- K+
BF,*OEt,, -78"C, 15 min
Ph
92%
-& /
OZN
OZN Batev. LA: Thadani, A.N.; Smil, D.V.; Lough, A.J. Synthesis, 2000, 990.
PhCIIO , Ni(dppe)Brz/Zn TIIF, 75°C Keck. G.E.; Wager, C.A. Org. Irtt., 2000, 2, 2307.
M 10 e-
93%
\ / 91%
Br , I n , D M F , r t
PhC€IO
b. F A ; Prahhudas, B. Tetrulzcdron, 2000, 56, 7595.
78% (92:s syn:anti)
Compendium of Organic Synthetic Methods, Vol 11
38
mBr , Sh/KF/HzO
PhCIIO
w
qumt
Ph
Li, L.-H.; i 3 a d . X . Tetruhedron Lett., 2000, 41, 5009.
mBr ,Cd,aqDMF
PhCHO
51%
Ph Synth. Commun., 2000, 30, 3517.
Zheng, Y.; Bao, W.;
O -H
Section 34B
1. TMSCl-NaI , MeCN, rt 2. Bio
Ge -
3. PhCHO Miyoshi, N.; Nishio, M.; Murakami, S.; Furuma, T.; Bull. Chem. Soc. Jpn., 2000, 73, 689.
l.
c-
*
68%
Ph
:;z:;:KyoM TMSCl , 6 h
96%
2. H,O Ph
OHC Kurohoshi, M.; Tanaka, M.; Kishimoto, S.; Goto, K.; Mochizuki, M.; Tetruhedron Lett., 2000, 41, 81. CHO
m
BrACOzEt
In,TIIF,rt,3h CozEt 95% ultrasound Lee.; Bang, K.; Lee, K.; Sung, S.-y.; Chang, S. Synth. Commun., 2001, 31, 3781. SiMe3
PhCHO
,YbC13, MeNNq
-u Ph
Fang, X.; Watkin, J.G.; Warner. B .P. Tetrahedron Lett., 2000, 41, 447. -snBu3
PhCHO
, 2 0 % ClCPh3 *
MqSiCl , CII2C12, rt Ph Chen. C.-T.; Chao, S.-D. J. Org. Chem., Z999, 64, 1090.
62%
65%
Section 34B
Alcohols from Aldehydes
39
0
II
0
I II
q
1. 2 eqBuLi
m
t.
"B-H N~s J (
2. PhCHO 77%
L OH
v. P, Emerschitz, T. Synth. Commun., 2001, 31, 961. I
, Mg/Iz
PhCIIO
t
q.0.1 NH4CI Zhang, W.-C.; J.i. C.-.I. J. Org. Chem., 1999, 64, 3230.
Ph
(allyl)2SnBr;?,HzO PhCHO
95%
t.
Cban.; Yang, Y.; Li, C.J. J. Org.
Ph Chem., 1999, 64, 4452. Ph
+ -
IFh BF4
\ /
Ma-(=)-
Chen, D.-W.; QchmJL . ' '
-
PhCHO , CC12
-
60%
0.1% NiC12, CC12
I
Ph A
O
Marx, A,;
A
I
B
~ , DCM, -78°C ~
s b
P~
10%(4-Br-2,6-di-t-Bu-phenoxyhAlMe Ph
Synlett, 1999, 584.
20%
c 93%
OH
Taylor. R.E.; Ciavani, J.P. Org. Lxtt., 1999, 1, 467. CHO
I
OMe
J. 01-8. Chem., 1999, 64, 6804.
Br
Ph
+
PhzCHOH
DMF, 25"C, 5 h
75 %
~
40
Section 34B
Compendium of Organic Synthetic Methods, Vol 11
OH
SnBu3
1 y
3qDMF,SnC14,12h -78°Crt Luo, M.; Iwahuchi, Y.;
Synlett, 1999, 1109.
PhCHO NaI , DMI , Sn12, , H,OTBN ,60"C ,47 h
*
OH
88%
++
Ph
(82
Masuvama.; Ito, T.; Tachi, K.; Ito, A.; Kurusu, Y. Chenz. Comntun., 1999,
*
0.1 Bu3SnH , 05 PhSiH3 AIBN ,PhH , 2 eq EtOII
Ph
*
HOs
p
h
1) 85%
(1.2
Hays, D.S.; Eu. (3.6Tetruhedron, 1999, 55, 8815.
79%
81%
Ph MeCN , 12 1120, It Iwai, 1.;Sugano, M. Tetruhedron, I999, 55, 7499. h
CI ro
''+6
, l o % Sc(OTQ
PhCI-I0
'I.;
I
+
l-butyl-3-mthylimidazolium Ph tetrafluomhorite (ionk liquid) . Chem. Commun., 1999, 1431.
.
Mivama.
18) 76%
126.
OH
(C€12=CHCI-12)4Sn
PhCHO
Ph
Loh. T.-P.; Xu, J. Tctmheriron Lett., 1999, 40, 2431.
PhCHO
(CII2=CHCII2)2Hg, 1120
80%
w
Chan.; Yang, Y. Tetmhedmn k t t . , 1999, 40, 3863.
Ph
Section 34B
Alcohols from Aldehydes
41
PhCIIO , AgOTf, CHzCl2 0°C , 15 min
WSEb C
Chataigner, I.; Piarulli, U.;
CSIITi-CHO
'
* E
1.2 Bu3sn-B~
h
85%
O
4A-JJ
BF3-K*
=+ SnBu,
c5k11 1
73% (77:23 E:Z)
Lee. AS.-Y,; Wu, C.-W. Tetruhedron, 1999,55, 12531.
Me<
P
Tetrahedron Lett., 1999,40, 3633.
ZdCeC13, PhH-THF ukrasound , 2 h
C,Ii ,SCIIO
L
C7H15 BF,OEtz, CHzQ2 -78°C Me 74% (>98:2 dr) Batev.;Thadani, A.N.; Smil, D.V. Tetruhedron Lett., 1999,40, 4289. Bu3SnH, BEt, ,02
I
toluene, -78°C
4
0°C
O r m Devin, P.; Fensterhacnk, L.; Malacria. M. Tetrahedron Lett., 1999,40, 5511. PhCHO , BEt, , hexandTHF ,rt
-
INi(x=)21,4 h
87%
Ph
90% (1: 15 Jyn:unti) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Angew. Chena., Int. Ed., 1999,38, 397.
2
PhCIIO , 3.3 ey ATPH 2.3 eq LIMP, -78°C w C 0 2 M e
toluenefilI F ATPH = tri(2,6-diphenylphenoxy)aluminum
%A/ Ph
97% Saito, S.; Shiozawa, M.; mote. I t Angew. Chrnt. Int. Ed., 1999,38, 1769.
C02Me
Compendium of Organic Synthetic Methods, Vol 11
42
Section 37
,catIn,Mn/TMSCl H,O, I d
1. &Br
PhCIIO
71%
/
2. HzO
Ph
AueC.;Luhin-Germain, N.; Thiaw-Woaye, A. Tetmhedron Lett., 1999, 40, 9245. ,Ga,KI
1. B-r
PhCIiO
THF , LiCl ,reflux
*Ph+
2. HzO 94% (54:46 Jynranti) Han, Y.; Chi, Z.; Huanp. Y. -ZLSynth. Commun., 1999, 2Y, 1287. SiMe3
, 5 min
dE
fiSiMe3 * MqSi TiCb , DCM ,-60°C Princet, B.; Anselme, G.; pornet. .I. Synth. Comniun., 1999, 2Y, 3329.
EtCHO
54%
REVIEWS: "Catalytic Asymmetric Organic Zinc Addition to Carbonyl Compounds", Chem. Rev., 2001, 101, 757.
SECTION 35:
u; Yu, H.-B.
ALCOHOLS AND THIOLS FROM ALKYLS, METHYLENES AND ARYLS
No examples of the reaction RR1 .-+ ROH (R1 = alkyl, aryl, etc.) occur in the literature. For reactions of the type RH 4 ROH (R = alkyl or aryl) see Section 41 (Alcohols and Phenols from IIydrides).
SECTION 36: ALCOHOLS AND THIOLS FROM AMIDES NO ADDITIONAL EXAMPLES
SECTION 37: ALCOHOLS AND THIOIS FROM AMINES 1. B uLi ,THF ,-45°C 2. H+ Me
Me
3. NaBH, , MtOII Bu Shieoya, Y.; Nagaoka, Y.; Yamada, K.4. J. Org. Chem., 2001, 66, 7051
74%
Alcohols from Esters
Section 38
43
'5
diethylene glycol, KOH 210"C, 12 h NH 2 Rahman, S.M.A.; Ohno, H.; N-
J
Ph
76%
3eq
OH
L \
Tetruherlron Len.,2001, 42, 8007. 2 eqIn, H20
Ph
. . ;-
*
ABr
85%
Ph
Winotapan, C.; Shinada, T.; Ohfune, Y. Tetruhedron Lett., 2001, 42, 9073.
SECTION 38: ALCOHOLS AND THIOLS FROM ESTERS NaBH4-LiC1, 5 min
* PhCH,OH 75% microwaves Jhg. J . - C Liu, B.; Dai, L.; Yang, X.-L.; Tu, S . 4 . Synth. Commun., 2001, 31, 1875. PhCO,Et
Q-M 0
Ph Kauch, M.; Hoppe. PhOAc
1. BuLi, TMEDA 2. TMSCl ~
97%
3.2MHCl Ph
D, Cun. J . Chem., 2001, 79,1736. sulfiiiatod bomhydride exchange resin
*
MeOI1,25"C, 10 min Bandcar. B.P.; Kamble, V.T. J. Chern. Rex (S), 2001, 54.
PhoH
94%
MeTi(Oi-Pr)3 , 4 eq EtMgBr
THF ,0°C Quan, L.G.;
Org. Lett., 2001, 3, 2745.
T i C b E n , C€I2CI2
e PhSH 87% 0°C , r t Jin, C.K.; Jeong, H.J.; Kim, M.K.; Kim, J.Y.; Yoon, Y.-J.; J.ee. S.-G. Syntett, 2001, 1956.
PhSAc
Compendium of Organic Synthetic Methods, Vol 11
44
Section 38
EtMgCl , Ti(Oi-Pr)4
OH
THF ,r t
81%
Lee, J.C.; Sung, M.J.; Cha. J.K. Tetmhedron Lett., 2001, 42, 2059. T i c k ,Li , THF , rt OTs
18 h
* +OH
Synthesis, 2000, 1575.
&y&A&
Zn(BH4)2 ,EtMgBr
C$ ,9-COzMe
-
1
THF, rt GI49 Balasuhramanian, S.; Nair. M.G. Synth. Contnzun., 2000, 30, 313.
.
B
n
\ e /O
O
T
Reddy, G.S.; Mohan, G.H.;
s
CeC13-7 HzO-NaI MeCN,6h '
* B
75%
76%
Et
n
\O O/
O
H
95%
Synth. Conintun., 2000, 30, 3829.
Ph2SiH2, cat PPh3, TI-IF, rt
cfi 19COZEt
98%
t Cfi19CHzOII 10% [ R h C l ( ~ ~ d ) ] 72 z, h Ohta.;Kamiya, M.; Kusui, K.; Michihata, T.; Nobutomo, M.; Furukawa, I. Tetruhedron Lc.tt., 1999, 40, 6963.
K S
COzMe
5 eq Mg , MtQH reflux, 30 inin
011
79%
Rho, H.-S.; KO, B.-S. Synth. Continun., 1999, ZY, 2875. 5 ~NaBII4,IIMF
MtQ &Coz*
MeOH, reflux , 1 h *Me0
Zanka.; Ohmori, H.; Okamoto, T. Synlcitt, 1999, 1636.
c&ori 98%
Section 39
Alcohols from Ethers
SECTION 39:
45
ALCOHOLS AND THIOLS FROM ETHERS, EPOXIDES AND THIOETHERS Et3Al, 5% Pl'h3, toluene
*
D
O
rt,ld
H '%It
99%
Et
Schneider. C.; Brauner, .I. Eur. J. Org. Cheni., 2001, 4445.
NaN3, € 1 2 0 , AlCh IIOZC
pH4,3O0C,3.5h
u-f r
.c
H02C
J+
99% N3
h p g g l l ~ F.: . Pizzo, F.; Vaccaro, L. Tetruhedron Lett., 2001, 42, 113 1.
I2 ,CII2Cl2, 10°C , 1 h
%,,,
Vatele.
92%
J.-M. Synlctt, 2001, 1989.
(90 v. J.S.; Arijaneyulu, S.; Ahmed, Md.M.; Subha Reddy, B.V. Tetruhedron Lett., 2001, 42, 2557.
o\
10) 90%
1.4e q M e 3 N ,1 eq H 2 0 DCM ,-2O"C, I h
0 2.H30' Wipf. P.; Rihe, S. Org. Lett., 2001, 3, 1503.
2 qAlEt3, I d imidazolium salt catalyst
*
uEt 76%
1%
Zhou, H.; Campbell, B.J.; &uv . en. S . T Org. Lett., 2001, 3, 2229.
"'OH
Compendium of Organic Synthetic Methods, Vol 11
46
Section 39
1. Li, 5% DTBB ,TI-IF 2. ZnBr2, THF 3 . 5 % Pd(PPh3),, THF, 60°C 4. HCl-HZ0 77%
Gomis, J. Tetrahedron Lett., 2002, 42, 5721.
NaN3 , rt , 6 h phase transfer ammonium PhL resin
Ph
0
-k
H
(9 1 Mahdavi, II. Tetruhedron Lett., 2002, 42, 8721.
;-
1. BuLi, DCM 2 . 3 eq Me3Al, 0°C + It
-p -
9) 95%
96% ( > 9 7 : 0 13-:1,2diol)
'
OBn
N3
Ph
OB n Sasaki, M.; Tanino, K.; J'vlivashita. M, Org. Ldt., 2002, 3, 1765.
Go
2.5 eq -78°C BuLi,+THF, rt 1 h
-JII 0
w 1 1
D M ; Stent, M.A.H.; Wilson, F.X. Org. Lxtf., 2001, 3, 3401.
C5H1 1
Et3AI, 5% P(NMed3 toluene ,rt , 1 d
Schneider.;Brauner, J. Tetruhedron Lett., 2000, 41, 3043.
Ylq
ye --
5
Me
5% Pd(PPh3)4, MezNH-BH3 Lc
3eqAcOH,DCM,rt,15min
Me
C02Bn 92% David, H.; Dupuis, L.; Guillerez, M.-G.; Guihe. F. Tetrahedron Lett., 2000, 41, 3335. CO$n
Section 39
Bt-0
Alcohols from Ethers
Ph
41
1.2.2eq BuLi
Ph%OH
2. HZO
ON:
v. A . R ; Fang, Y. Heterocycles, 2000, 53, 1783. 1. MgSiN, ,Bu4NC1 , neat
*
2. P-TsOH, MeOII
. ,
40%
Bu
Synlett, 2000, 1840.
89%
% ",,
BF3*OEt2,DCM
aOv
75%
Prestat, G . ; Baylon, C.; &&. M.-P.:
/
solid phase microwaves , DMF , 4 min
/
* H
Kumar.;Anjaneyulu, S.; Reddy, B.V.S.; Yadav, J.C. Synlett,
Noguchi, Y.; Yamada, T.; Uchiro, H.;
O
2000, 1129.
W
92%
(95 5) 84% Tetrahedron Lett., 2000, 41, 7493, 7499.
48
Compendium of Organic Synthetic Methods, Vol 11
ON3
1. Th4SN3 , Cr-salen catalyst
[emim] SbF6,20°C
2. CSA , MeOH * "'~8Il#OH Sonr.; Oh, C.R.; Roh, E.J.; Choo, D.J. Chem. Coinmun., 2000, 1743.
(90 oor. N,; Kazemi, F. Synth. Continun., 199Y, 29, SGl. 2% TiQ(OTf), MtOH
P h it^^^
Section 39
0°C , 5 min
75% (87% ee)
10) 93%
-
MeO 95% (89% ee)
Iranpoor, N.; Zeynizadeh, B. Syntlz. Cornniun., Z999, 2Y, 1017. 1 . 2 q A l C 1 3 , 2 q NaI
Ph-OMe ci.
2.5% Na2S203 Asghari, J. Synth. Cornniun., 1999, 29, 973.
m;
*
Ph-OH
98%
-
Li naphthalenide , THF -78°C rt , 10min 0
Jankowska, R.; Mhehe, G.-L.;
b. H. -J, Cheiii. Continun., 1999, 1581.
78%
1 . 2 q i-PrSNa, DMF 1GO"C , 4 h P
h
\ e /S
S
M
e
2. aq HCI
Pinchart, A,; Dallaire, C.; Van Bierheek, A.;
93% Tetmhedron Lett., 1999, 40, 5479.
1. Hg(OAc)z, TIIF/II20 2. NaBHdaq K2C03
OH 62% Crouch.; Mehlmann, J.F.; Herh, B.R.; Mitten, J.V.; Dai. G , Synthesis, Z999, 559.
Section 40
Alcohols from Halides
x
I
I
A/
Ph
49
2. l.K”’lrz HzO
-
€
SiMe,
1
I HO/,
4
Ph
Ph
m . Geng, ;F. Org. Lett., Z999, I, 1115. 1
21%
I.
Additional examples of ether cleavages may he found in Section 45A (Protection of Alcohols and Thiols).
SECTION 40:
ALCOHOLS AND THIOLS FROM HALIDES AND SULFONATES 1. Mn*, TIIF, rt 2. PhCHO ,THF
Ph-OMS
*
1. BEt3, DCC , DCE -50°C. syringe pump
2. M e o r r ; ~ q ~
I
Kihara, N.; Ollivier, C.;
*
2. EtCHO
82%
+OPh
Org. Z*.rf., 1999, 1, 1419.
1. B u N g L i ,TIIF,U’C, 0.5 h
PhBr
72%
OH
othm ekctrophiles can he used Kim, S.-H.; Rieke. R.D. Tetrahedron Lett., Z999, 40, 493 1.
oir
9”
t
Ph Inoue, A,; Kitagawa, K.; Shinokubo, H.; Qshima. K. J. Org. Client., 2001, 66, 4333. 1. FSM-16 , N a I , hv , acetone, r t , 1d
PhA
v
B
r 2.FSM-16, CsI , h v , i-PrzO, 12 h
t
wcrro
Ph
Itoh. A.; Kodama, T.; Inagaki, S.; Masaki, Y. Org, Lett., 2001, 3, 2653.
86x8 1%
50
Section 41
Compendium of Organic Synthetic Methods, Vol 11
SECTION 41: ALCOHOLS AND THIOLS FROM HYDRIDES
90% conversion
u; Feiten, H.-J.; Chang, D.; Duetz, W.A.; van Beilen, J.B.; Witholt, B. J. Org. Chem., 2001, 66, 8424.
5
HO cultured cells of Gocsypium hirsutum I1II1II1I
11l111111
Hamada.;Tanaka, T.; Furuya, T.; Takahata, H.;Nemoto, II.
72%
Tetruhedron Lctt., 2001, 42, 909.
’)
0
,acetone
0°C , 5min ;-
A
Ph
Ce(OTf), ,MeCN, rt
OH
4 li: Ph
+ +
doH 21%
79% DAccolti, L.; Fusco, C. Tetruhedron Lxtt., 2001, 42, 7087.
Ph
1 5 % I-r,o 9.5% 16.40/0HzO 99:7% Laah.;Herbert, M.; Cushnyr, B.; Bhatt, A,; Terrano, D. 3. Chem.. Soc., Perkin Truns. 1, 2001, 578.
DDQ , TfOH , rt , 10 h
85.7% -
4OH
;Suzuki, T.; Nishida, Y.; Satsurnabayashi, J. Chem. Soc., Perkin Truns. 1, 2001, 3230.
K.; Horaguchi, T.
89%
51
Alcohols from Hydrides
Section 41
Cu(N0+3 H 2 0 , MeCN
Nasreen, A.;
w
Ph
phosphate buffer, 50°C 30% H 2 0 2 , 5 h Org. Prep. Proceed. Int.. 2000, 32, 287.
B. meguteriwn
QH
96%
63% conversion (74% ee ,R)
Ph Adam, W.; Kukacs. Z.; Harmsen, D.; Saha-Moller, C.R.; Schreier, P. J. Org. Chem., 2000, 65, 878.
-'"oh
no N
Splzingonwnus sp. HXN-200
I
2% glucose , 5 h
B oc
Chang, D.; Witholt, B.;
0
N
I
80%
Boc
Org. Lett., 2000, 2 , 3949. Bucllus me.gu&riunt 0 2
79%
,30°C, 17 h
. ; Saha-Moller, C.R.; Weckerle, B.; Schreirer, P. Adam, W.; Eur. J. Org. Chem., 2000, 2923. Pbreu~loinonu.s ofeovorms GPol C N - B n
I 'O+
*
4%
c N I B n
62%
u; Feiten, H.-J.; van Beilen, J.B.; Duetz, W.; Witholt, B Tetuhedron Asyinm., 1999, 10, 1323.
Oz ; 10%NHPI , 2 % Bu4NBr
P hCF, , HZO
Matsunaka, K.; Iwahama, T.; Sakaguchi, S.;
60% (73% conversion + 23% diol) Tetruhedron Lett., 1999, 40, 2165.
Compendium of Organic Synthetic Methods, Vol 11
52
&
CO,Et
.
0, , 5%Mt1(OAc)~*4 HZO DCM ,23"C, 14 h
Section 42
bOH COzEt
Ic
J. Org. Chein., 1999, 64, 7668.
89%
OH
I
Mn-sabn catalyst , PhIO
5X% (19% ee)
Punniyamurthy, T.; Katsuki. T. Tctruhedron, 1999, 55, 9439.
Yoshida, Y.; Ogura, M.; w e . Y. Heterocycles, 1999, 50, 681.
65~70%
SECTION 42: ALCOHOLS AND THIOLS FROM KETONES The following reaction types are included in this section: A. Reductions of Ketones to Alcohols B. Alkylations of Ketones, forming Alcohols
1
BuOII , 5%KUC12(PPh3)3
LBu
KOII , dioxane , 4 0 h * Ph C.S.; Kim, B.T.; Kim, T.4.;w.S .6 J. Org. Cheni., 2001, 66, 9020.
Ph
80%
Coupling of ketones to give diols is found in Section 323 (Alcohol + Alcohol).
Section 42A
53
Alcohols from Ketones
SECTION 42A: REDUCTION OF KETONES TO ALCOHOLS ASYMMETRIC REDUCTION 1. (-)-Ip2BII , THI' , 2 d 2. NaOH , I 1 2 0 2
Et
Et LCD2H 82% (95% e e , R )
-1 -1
Bjlmachandran. P.V,; Brown, H.C.; Pitre, S. Org. Lcctt., 2001, 3, 17.
A
bakers yeast ,pet etherA120 , rt , 1 d
Ph
Ph
Llu.;Zhu,
-
62% conversion (90% ee ,S)
T.-S.; Sun, P.-D.; Xu, .I.-H. Synth. Conzntun., 2001, 31, 1521.
ji
RuQ(cymene)2, HCOOI-I, NEt,
99% (97% ee) dendritic ligand , 20 h Ph Ph Chen, Y.-C.; Wu, T.-F.; J.-G.; Liu, 11.; Jiang, Y.-Z.; Choi, M.C.K.; Chan, A.S.C. Cheni. Cotnniun., 2001, 1488.
L
Ph
3% CuCl, 3% NaOt-Bu, 3.5h 3 % (R)35 -xyl- MeOBIPHEP 0.34 PMHS ,0.S M toluene -50°C
QH
b
--
Ph
95% (95% ee) Llpshutz. B.11.;Noson, K.; Chrisman, W. J. Am. Clzena. Soc., 2001, 123, 12917. R U(S-Tol-P-Ph0s)PhII)Clz C02Bn
C 0 2 Bn
N2 , 80"C, 2 h
Wu, J.; Chen, H.; Zhou, Z.-Y.; Yueng, C.H.;
b. A.S.C, Synlett, 2001,
cat [Rh(cod)(02CCF3),], toluene
-x
quant (98%ee) 1050. 90% (72% e e , R )
C02Bt 50°C. q6-arenechromium diphosphines CO2Et Pasquier, C.; Pelinski, L.; Brocard, .I.; Mortreux, A,; A_Ehossou-Niedercorn. F, TetruhecironLEtt., 2001, 42, 2809.
54
Section 42A
Compendium of Organic Synthetic Methods, Vol 1 1
a
1. i-PIOH , t-BuOK , H 2 0 , rt aminosulfonamide ligand 2. [Cp*IrCl2]2 ,40°C, 2 h
1
*
Ph
3. add ketone, aq i-PIOH t-BuOK, 1 d T h o r p , T.; B.-cker, J.; Brown, S.M.; Buhert, C.; Croshy, Tetrdedron Lett., 2001, 42, 4041.
Ph
97% conversion (97%ee,R)
; Fitzjohn, S.; Muxworthy, J.P.;
S d 2 f i i @ , THF ,-78°C 2h OMe
0
OMe
92% (75% de , S) Fukuzawa. S.-i.; Miura, M.; Mahuzawa, H. Tetruhedron Lett., 2001, 42, 4167.
p --
Bakers yeast
"zEt
liquid petrokum gas*&C02Et
74% (95% ee) Johns, M.K.; Smallndee. A,.1.: Trewhella, M.A. Tetrulzerlron Lett., 2001, 42, 4261.
A
1. proline ligand , DCE , 2 % Ru complex 4
2. I-ICOOH ,NEt, Ph Rhyoo, H.Y.; Yoon, Y.-A.; Park, H.4.;
96% (79% ee) Tetruhedron Lett., 2001, 42, 5045.
[hmim] PF, , II,O, MeOH imimhilized Bakers yeast
Howarth..;James, P.; Dai, J. Tetruhedron Lett.,
* D
O
H
35%
200Z, 42, 7517.
RuCl3lS-Tol-BIN AP
99% ee
H2 (4 bar), MeQH, 1 d OMe Madec, J.; Pfister, X.; Phansavath, P.; Ratovelomanana-Vidal, V.; Genet, J.-P. Tetruhedron, 2001, 57, 2563.
A
Ph Salvi, N.A.;v-
Rhizopus urrliizt~s
e
33% (69% e e , S) . ay.
S. Tetrultedron, 200Z, 57, 2833.
Alcohols from Ketones
Section 42A
&
55
0 OH -
Baker; yeast, 30°C ,OEt
fi-
54% (75% ee)
,OEt
HzO , 1 d
OEt
OEt
0 0 Attolini, M.; Bourguir, F.; Iacazio, G.; Peiffer, G.; M a f f e l . T e t r u h e d m n , 2001, 57, 537.
A
B H 3 * S M ~10% , c h i d Al akoxide
Ph Fu, I.-P.;
toluene, 40"C, 10 inin Tetrultedron Asymm., 2001, 12, 45.
96% (73%ee)
Ph
Bakers yeast/suanse, rt
* L N 3 phosphate buffer , pH 6.5 ph 92% (100% ee ,R ) 18h b d a v . J.S.; Reddy, P.T.; Nanda, S . ; Kao, A.B. Tetruliedron Asymm., 2001, 12, 63. N3
Ph
Baken: yeast 48% (>96% ee ,S)
Weui, Z.-L.;
Lt. Z.-Y.: Lin. G .-OLTctruhedron Asymm., 2001, 12, 225.
A 0
y
i-PrOH ,20"C, 4 h
Ph
3% [
Bied, C.; m
u
*
NHCO Nf Ii-Pr
I"'
N Hz
/0.5 KuCLz@-cymeiw)]
. J.J.E.; Man, M.W.C. Tetruhcclron Asymm., 2001, 12, 329. i-PrNEtPh*BH3,THF, 25°C
Ph~
75% (63%e e , R)
Ph
s o z T o l
(3; .N
n' \
Me
Cho.; Kim, D.J. Tetruhedron Asymm. 2001, 12, 2043.
*
QI I I
&S q T o l
Ph
98% (>W%ee ,S)
56
Section 42A
Compendium of Organic Synthetic Methods, Vol 11
Curvuluriu luncltu , 10 h Phj i S O 2 P h
QH -
+A
SOzPh 90% (87% ee ,S)
Ph
Gotor, V.; Reholledo.; Liz, R. Tetruhdron Asyrnm., 2001, 12, 513. carhonyl rtxuctase S1 C02Et quant (>99% ee ,S) Yasohara. Y .; Kizaki, N.; Hasegawa, J.; Wada, M.; Kataoka, M.; Shimizu, S. Tetruhedron Asynim. 200I, 12, 1713.
A
=A
BH3-SMe,, squaric acid ligand
95% (95% e e , R) Ph toluene, 50°C Ph Zhang, J.; Zhou, €L-B.; Lii,S.-M.; Luo, M.-M.; Xie. R.-G.; Choi, M.C.K.; Zhou, Z.-Y.; Chan, A.S.C.; Yang, T.-K. Tetrahedron Asymiiz. 2001, 12, 1907.
A A
P h S i H ? , cat [Kh)cod)ClI2 , neat
Ph
cyclic ke timine ligand
-A Ph
v. Keyserlingk, N.G.; Martens. J. Tetruhedron A.ryinm. 2001, 12, 2213.
86% (54% ee)
-A
BH3-oxazahoiulidine , amino-alcohol ligand
92% (74% ee ,S)
THF Ph Feng, Y.; Hang, .f.-F. Tetruhedron Asytiinz., 20UZ. 12, 2323.
Ph
*A
1%chiral Ru compkx , i - M I I
Ph
Lutsenko, S.;
4
Ph
1
micmwaves , 9 min Ph Tetruhedron Asyntm. 2001, 12, 2529.
90% (82%e e , R)
QH Ywuufuzyiriujurinosu IF0 10896 I d
-
*P
h
q
91% (>99% ee,S)
OH 0 1I Tsujigami, T.; Sugai, T.; Ohta. 11. Tetrulrerlron Asynrm. 2001, 12, 2543.
Section 42A
0
I1
Ph Lin, Y.-M.; Fu, I.-P.;
Alcohols from Ketones
BH,-SMe,, DCM , 10% Al(Oi-Prh 21% hinaphthyl ligand ,0.5 h
57
PH - /Z
95% (71% e e , ~ )
Ph
m.B.-1. Tetruhedron Asymni. 2001, 12, 3217.
1
1. PhSiH3, CuF,/S-BINAP toluene , rt , 2 h
79% (78% ee, S) Ph Sirol, S.; Couriiiarcel, J.; Mostefai, N.; R l d n t . O r g . Lett. 2001, 3, 4111. Ph
A
Ph
2. ay HCI
i-Pa11 , cat RuClz (PPh3),
20" , tetramine ligand , 2d
-
A
44% conversion 44%e
Ph
Marson.;Schwarz, I. Tetruhetlron Intt., 2000, 41, 8995.
S,S-Ru catalyst, 27°C:
(9S%ee,S)
*
-f
HCOOII , NEt, , 12 h
0 OH Okano, K.; Murata, K.; M y a . T. Tetrahedron L a . , 2000, 41, 9277.
A c&.',
NaBII4 / MqSiCI , TIIF, 25°C
Ph
10%
PI1
-
-1
98% (96%e e , R )
Ph
HO Jim:. B.; Feng, Y.; Zheng, J. Tetruherlron Lett., 2000, 41, 10281.
A A
oxazohorolidine catalyst , TIIF
Ph BH,*SMq, rt Santhi, V.; Rao, J.M. Synth. Cnmntun., 2000, 30, 4329.
Ph
ofr
* A
chiral P-diamine , BH3*'I'€IF , THF -15"C, 2 h
Sato, S.; Watanabe, H. Chent.Lett., 2000, 990.
88% (70% ee)
Ph
* A Ph
88% (92%ee, R )
58
Compendium of Organic Synthetic Methods, Vol 11
Section 42A
cat [Rh(cod)z] BF4 , Ph2Si€Iz
chiral his-phosphine , THF , 4 0 ° C
Kuwano, R.; ; Shirai, J.; Takahashi, M.; Jto. Bull. Chem. SOC. Jpn., 2000, 73, 485. BH3.THF ,proline, T H F
*
rt , 10min
90% (91% ee)
Y,
1
quant(85%ee)
Ph TeodomviC, A.V.; Joksovik, M.T.,.; Konstantinovie, S.K.; Mojsilovie; Mihailovie, M.L. Monut. Chem., 2000, 131, 91.
'k
Bakers yeast, 1 d
=
Ph
Ph
75%(97%ee)
N-OMe N-OMe Kreutz, O.C.; Segura, R.C.M.; Rodiigues, J.A.R.;Moran. P.J& . .Terruhedron Asynttn., 2000, 11, 2107.
A
Geotrichutii cunrlitlr~rilimmobilized resting cells
* A A . -A
51% (>99% ee ,S)
. . super cr itica 1 CO, Ph Ph Mdtslada.;Harada, T.; Nakamura, K. Chent. Conimun., 2000, 1367.
1
ph
Ru catalyst, Hz , I-PiOH t-BuOK
*
Ph
9 8 % ~
. . Org. Lett., 2000, 2, 4173. Burk,;Hems, W.; Henberg, D.; Malan, C.; h t t i -GtraSLL&
A
aryl oxazaphospholidine oxide
BII3 ,THF Ph Ph Brunel. J.M.; Legrand, 0.;Buono. G. Eur. J. Orb. Chem., 2000, 3313.
95% (32% ee)
Cutvuluriu lunutu CECT 21 130 phosphate buffer, pH 6 , MeCN Dehli, J.R.; &&or. V. Tetruherlron A~pittii.,2000, 11, 3693.
55% (96% e e , S )
Section 42A
Alcohols from Ketones
59
OH
--
Synechococcus sp FCC7942 9d
51% (98% ee ,S) Yamanaka, R.; Tohi, K.; IIamada, €1. Tetruhedron Lett., 2000, 41, 6799.
Nakam-;
chiral perfluoro s a k n ligand ,70"C [Ir(cod)Cl]2 , i-PiOH , D- 100, KOH
0
II
A
OH
I
2d Ph Maillard, D.; Nguefack, C.; Pozzi, G.; Quici, S.; Valadb, B.; Tetruherlron Asynzm., 2000, 1 1 , 2887.
A
chiral oxazahoroline ,BHj.SMe2 1XF,rt, 2 h
Ph
I\
.r
Ph
*A Ph
Santhi, V.; h o . J.W Tetruherlron Asymnz., 2000, 11, 3553.
91%(56%ee)
94% (93% ee)
L
Hz (40 bar) , cat diamine-BINAP L
C
0
2
M
e
MLOH, S O T , 14 h
COzMe
quant (99% ee)
ter Halle, R.; Colasson, B.; Schulz, E.; Spagnol, M.; Tetruhedron Lrtt., 2000, 41, 643. H
A
4
2 BI-13 , THF Ph Jones.; Atherton, J.C.C. Tetruhedron Asynim., 2000, 11, 4543. Ph
>95% (84% ee)
Ceotrichuni canriiriuni I F 0 4597 Amherlite XAD-7 83% (94% e e , S) Nakamura. K.; Fujii, M.; Ida, Y. J. Cheni. Soc., Perkin Truns. I, 2000, 3205.
60
A
*x
0.1 chiral diamine ,BH3*THF
THF ,rt
Ph Sato, S.; Watanahe, H.;
A
Ph Tetruhedron Asynirti., 2000, 11, 4329.
'
40 hw H2, i-PaWt-BuOK
chiral polymer catalyst S O T , 18 h ter Ilalle, R.; Schulz, E.; Spagnol, M.;
.
.
Cr(L-His)+ , DMF-€120
rt ,pH 6.5
0
Hajdu, C.; Jekij, J.; IRvai, A,; Tetruherlron Lett., 1999, 40,1373.
A
Ph Synlett, 2000, 680.
-
ph?
Ptk fI2N
OH
33% (36% e e , S)
; Zucchi, C.
2 eq LiBH4/Ni12, TIIF
Ph
88% (87% ee)
quant (68% ee)
Ph
;-
Section 42A
Compendium of Organic Synthetic Methods, Vol 11
*
Ph
H
Ir:
Ph
OII
94% ee
Molvinger, K.; Lopez, M.; Court. .I, Tetruhedron L t t . , 1999, 40,8375.
A A
CpRhCl(chird diamine) , 12 h
Ph Murata, K.;
Ph
*
i-PrOH ,t-B uOK ,30"C J. Org. Chent., 1999, 64,21XG.
9-- H
A
92% (94% e e , R)
Ph
10,l l-dihydrocinchonidine ,AcOH 1% PdlAIZQ , 17"C, 5.8 h~ H2 CO&t
Phd a z E t
LeBlond, C.; Wang, J.; Liu, J.; Andrews, A.T.; Sun. Y.-K, J. Am. Chem. Soc., 1999, 121, 4020.
1%
>'\B-Me Me0 ' 0
BH,*SM%, THF, rt
*
91%ee,R
1
Ph Puijaner, C.; Vidal-Ferran, A.; Moyano, A.; perichs. M.A.; Riera, A. J. Org. Cherir., 1999, 64,7902.
>99%(96%ee)
Section 42A
Alcohols from Ketones
jl.*
+ a
bakers yeasf, petm 4 0 6 0
Ph
4"C,7d
61
P[I/..
-
Ph
cinchona rmdifkd Pt catalyst & 0 3 , H 2 , 60 b a r , 25°C
++
AcOH , MeOH OMe OMe Studer. M.; Burkhardt, S.; Blaser, H.-U. Chcnt. Conintun., 1999, 1727.
Ph
Bolm.;Derrien, N.;
PhL
C
O
z
59%
; Ten, A.; Trewhella, M.A. Org. k t t . , 1999, 1, 1879.
Florey, P.;
-
BI-I3*SMq , THF, It 10%dendritic chiral catalyst
96% ee
QH
A
Ph
80%(89%ee)
Seger, A. Chern. Cornmun., 1999, 2087. 1. DlP-Cl, NEt,, 1'HF
H
2. aq OH; aqH+
- Lmz Ph
DIP-C1 = B-chloro diisopinocampheylhor~ne
87% (98% ee)
u; Zhao, C.; Pierce, M.E.; Fortunak, J.M. Tetrulzcdron Asymm., 1999, 10,225.
A
*
92% (73% e e ,S )
Ph
BH3*SMq, toluene, 25°C Yane.;Lee, D.-S. Tetruherlron Asyrnnt., 1999, 10, 405.
Tommasino. M.L.; Thomazeau, C.; Touchud, F.; Tetruherlron Asymrn., 1999, 10, 1813.
ji
*x
10%c h i d pyriulidine alcohol
Ph 12% M(OEt), , BII3-SMez Ph Yanagi, T.; Kikuchi, K.; Takeuchi, 11.; Ishikawa, T.; Nishimura, T.; Chem. k,tt., 1999, 1203.
quant (97.5% ee)
a
62
Section 42A
Compendium of Organic Synthetic Methods, Vol 11
A
20%
-
&IM'
BH
x
, BH3-SMe2t
91% ee
Ph THF , S O T Ph Li, X.; Yeune. C .-h ... Chm. , . A S.C.: Yanp T.-K. Tetruhedron Asymm., 1999, 10, 759.
1
*
95%991%ee)
zpie -
chiral G a complex Ph Ford, A.; W o o d w u Angew. Chmi., Int. Ed., 1999, 38, 335.
1.0.1 Ph&OM.
N-4
-
OH t
ph/YoMe
2. PhNEt,*BH,, THF , 25°C OMe OMe Cho. B.T.; Chun, Y.S. J. Clzem. Sor., Perkin Truns. I , 1999, 2095.
..
OH ---
BH,.OEt,, LR, THF Ph
93% (95%ee)
quant (95% ee)
P h A ,
Me Ford, A.; Woodward, S. Synih. Cornmun., 1999, 29, 189.
Cnlmes. M.; Escale, I;. Synth. Cornmiin., 1999, 29, 1341.
YKER-1 enzyme NAD PI I 0
- _.
QH
Y3H7 0
92% (>99%ee , S)
Kawal.;Hida, K.; Tsujimoto, M.; Kondo, S.4.; Kitano, K.; Nakamura, K.;Ohno, A. Bull. Chem. Soc. Jpn., 1999, 72, 99.
Section 42A
Alcohols from Ketones
L ~ B I ITIIF, ~, 2
0
63
~
chiral Lewis acid
Nozaki.;Kohori, K.; Uemura, T.; Tsubumi, T.; Takaya, H.; Hiyama, T. Bull. Chem. SOC.Jpn., 1999, 72, 1109.
NON-ASYMMETRIC REDUCTION
Iph
NiClz , N&H4
*
88%
Ph THF , r t , 15 min Khurdnd.; , . Chauhan, S. Synth. Conitnun., 2001, 31, 3485. Ph hP’
0-o
eoH
aq TiC13 , NH3, MeOH
*
0°C
68%
Clerici, A.; Pastori, N.; P o r t a . E i i r . J. Org. Client., 2001, 2235.
Bae, W.; Lee, S.H.; Jung, Y.J.; Yoon, C.-O.M.; yoon. C& Tetruhedron LL’tt., 2001, 42, 2137.
t
-
B
u
O
O
PhSiIi, , M n ( d ~ m ) ~* t DCM , i-PiOH,O2 ,rt
-
II
A
Ph
0.2% RuC12(I’Ph3X ,2.4% NaOII 0.4Yb(OTQ3, i-PiOI-I, reflux
*
l h
u
A
1-1, , 10% Pd/C-ethylenediamine
Ph
MeOH,3h
*
Tetruherlron, 2001, 57, 4781.
O
H
74%
xph
Ph Matsunaga, H.; Yoshioka, N.; u d d . T. Tetrahedron LElt., 200I, 42, 8857.
..
O
98% (14:l trans:cis)
Magnus. P,; Fielding, M.R. Tetruhedron Lett., 2001, 42, 6633. 0
B
Ph
96%
64
Compendium of Organic Synthetic Methods, Vol 11
Section 42A
MedI Mqo @ @ L ~ A ~ H ( O ? - B THF U)~,
N
'zbc
t
J
-78"Cd
80%
18°C
N-J
BZ'
IIuang, H.-L.; Wang, C.-L.J. Tetruherlron Lett., 2001, 42, 1329.
Me rulius t~r?m~Unsus
MeO
MLO
61%
c1 c1 Petra, D.G.I.; Field, J.A.; Schipper, D.; Wignherg, J.B.P.A.; Karner, P.C.J.; Reek, J.N.H.; van Leeuven, P.W.N.M.; Wever, R.; Schoemaker, H.E. Tetruhedron Asymm.. 2001, 12, 1025.
;.A-
&
BH3oTHF ,THF, ~ f l u x
-6
\\,*\\\'\\
81% (>99.5% trans)
Cha.;Moon, S.J.; Park, J.H. .I. Org. Chcni., 2001, 66, 7514.
Ph
Ph
-
Lfi
1. FH3{P(C,H,,),)], toluene -78°C
It, 15 h
OH 2. aq H+ Ahernathy, C.D.; Cole, M.L.; Davies, A.J.;
*
Ph
-
quant
OH Tetruhedron Lett., 2000, 41, 7567.
Na2C03 , 13S"C, 12 h 5% Pd(0Ac)z ,2 eq KOAc
Ph
DMF
a
Quan, L.G.; Lamrani, M.; Yamamo
Ph Phukan, P.; &&&u-& '
69% J . Aria. Chent. Soc., 2000, 122, 4827.
inacmcyclic Ni catalyst
*
KOH ,i-PIOH , 82°C Syntli. Corriinun., 2000, 30, 2401.
A
Ph
78%
Section 42A
Alcohols from Ketones
Po
Hayakawa, R.; Sahara, T.;
Bn\
'$
Ph
Tetrulzdron Lett., 2000, 41, 7939.
Ti(0i- Pr),
H;#::)
* Bn\
K-Selectride ,TIIF -100°C , 15 inin
OH
1
Np
c'. CPh Bn,
N
(> 100 O H . OH Tetruhodron Lett., 1999, 40, 593.
Lawson, E.C.; Zhang, H.-C.;
Ph
65
1 . 5 e q C ~ S i H , C I 1 2 C 1 21, 2 h
C
N-CIIO
,o"C-.
rt
1) 91%
-
Iwasaki, F.; Onomura, 0.;Mishima, K.; Maki, T.; Mntsumura. Y. Tetruherlron Lett., 1999, 40, 7507. 3 eq SmI2,2 eq H 2 0 0°C , 1 h k k . G E ; Wager, C.A.; Sell, T.; Wager,
*
96% (83:17 a n & ~ y n )
T.T.J. Org. Chenz., 1999, 64, 2172.
K( T ~ ~ PHBn ) ~ B,THF Trip = triisopmpylphenyl
85% (>99%cis)
Smith. K.; El-Hiti, G.A.; Hou, D.; DeBoos, G.A. J. Cheni. Soc., Perkin Truns. I, I999, 2807.
6G
Section 42B
Compendium of Organic Synthetic Methods, Vol 11
NaBH4, Si02 , hexane
2
0°C , 1 h Yakahe, S.; Firano. M.; Morimoto, T. Synth. Commun., 1999, 29, 295.
Ph
0
p h ~ c H @ ~
BuzSnH2-BusnFz, THF rt,2h
OH
0
+ IIMPA + LiI
89% 0% 0% 83% Moriuchi-Kawakami, T.; Matsuda, H.; Shihata, I.; Miyatake, M.; Suwa, T.; Bull. Chern. SOC.Jpn., 1999, 72, 465.
OH 94% (63:1 synzanti)
m o l r n . E.J.; Schulte 11, J.P. J. Org. Chem., 1999, 64, 2610. REVIEWS:
"Enantioselective Reductions hy Chirally Modified Alumino- and Borohydrides", Daverio, P.; Tetruliedron Asynim. 2001, 12, 2225.
SECTION 42B: ALKYLATION OF KETONES, FORMING ALCOHOLS Aldol reactions are listed in Section 330 (Ketone-Alcohol)
ASYMMETRIC ALKYLATION
LCN
Ph
Dehli, J.R.;
Cuivuluriu lurwtu EtOH
---
QH b
Tetruhedmn Asymm. 2001, 12, 1485.
P h / Y C N Et
69% (98%ee)
Section 42B
A
67
Alcohofs from Ketones
*A
Ira(cod),.hiral amino-alcohol sulfoxide
99% (65% ee) Ph Petra, D.G.I.; Kamer, P.C.J.; Spek, A.L.; Shoemaker, H.E.; van Leeuven, P.W.N.M. J. Org. Chenr., 2000, 65, 3010. Ph
A
HCOOIVNEG ,6O"C, Hz
0.25 [R~Cl~(p-cyrnene)]~, Hz , 0.7 h
2% chin1 amino-alcohol 2.5%i-ROK, I-PiOH Alonso, D.A.; Nordin, S.J.M.; Roth, P.; Tamai, T.; J. Org. Chent., 2000, 65, 31 16.
Ph
*A Ph
97% (94% ee)
..
(CIIZ=CHCI~~)~SII, DCM ,rt
R-B inal-Ti Ph Ph Casolari, S.; DAddario, D.; Tanliavini. . Org. k t f . , 1999, 1, 1061.
70% (55%ee)
NON-ASYMMETRIC ALKYLATION
+ 0.1 CUI (NO TMSC1,NOCuI (63% b e . P a ; Ahn, H.; Lee, K.; Sung, S.-y.; Kim, S. Tetruhedron ZAL,
/g
60%
-1 )
2001, 42, 37.
mBr ,Sin, THF
* I1% Ph rt ,20inin Ph Basu, M.K.; Banik. B.& Tetruhedron Lett., 2001, 42, 187,
Cdhezds.; . ,, Pereira, A.R.; Amey, A. Tetruhedron L.&t., 2001, 42, 6819.
80%
96%
68
Section 42B
Compendium of Organic Synthetic Methods, Vol 11
A
Ph Kamhle, R.M.;
Sn(CH2CH=CH2)4,DCE
10% CU(OTQ2,lOh
y I ' Ph
72%
m.V.K. Tetruhedron Lett., 2001, 42, 7525.
,TIIF,rt C&Ti(OPh), Tctruherlron Lett., 2001, 42, 8567.
Quan, L.G.;
&
9Me
63 %
0
/I
A
f P
N-Rn
S d , , acetone, THF , rt
-Bn
sqPh
*
OH
Yoda. H.; Ujihara, Y.; Takahe, K. Tetruhedron L.ett., 2001, 42, 9225.
A
Ph
1. H O C C I I Z B r , N d , Dy THF, HgC12, -14°C
2.H 2 0
+
Ph
-
Li, Z.; Jia, Y.; U o u . J, Synth. Conintun., 2000, 30, 2515.
ori
I Ph4
0, , pivaklehyde , MeCN, rt
Co salen complex , 8 h
0
k
II
*+ r \
Ph
Fernindez, I.; Pedro. J.E.; RosellB, A.L.; Ruiz, R.; Castro, I.; Ottenwaelder, X.; Eur. J. Org. Chern., 2001, 1235.
1. Tic& 2. MeMgC1-CeQ , ether M%N
3.II,O+
75%
,llllw~
MqN
85% (>98% de) Bartoli. G,; Bosco, M.; Marcantoni, E.; Massaccesi, M.; Rind&, S.; Sambri, L. Tetruhedron Lett., 2001, 42, 6093.
69
Alcohols from Ketones
Section 42B
S d z , cat NiI, , TIIF
OH
0
m.G.A.; Le Huirou, Y . ;Brown, G.A. J. Org. Cltem., 2002, 66, 4511.
a
0
04.
OH
1. M e %Me TiCb ,DCM
-78T , 15 rnin OMe 2. -78"C, 15 n i n ~
S
I
CqMe
I
B
~
+
CaMe
~
63% 20% Ghosh. A.K.; Kawahama, R.; Wink, D. Tetrahedron Lxtt., 2000, 41, 8425. 1 . TinI,(l>ME), , DME , <1 min ph?
I
2 . 4 - t -hutylcyclohexanone 3 . X I NH4CI
Wvans. W.J.; Allen, N.T. J .
h i .
* % ' -tB"
99% (79:21 u x e q ) Cheni. Soc., 2000, 122, 2118.
e- (Hg cathode) ,0.1 MTBAeBFd DMF-pyridine , DMQQ BF4
HO,.,
DIN02 BF4 = N,N-diinethylquiniun tetra fluorohorate , .
A&
Singh, A. Synlett, 2000, 1199.
-
96%
Sn(CH2CIi=CH2), , DCM
Ph
10% Zn(OTQz, 10%PhNMe2 OH It, Id Tetruhedron Lctt., 2000, 41, 9883. Hamasaki, R.; Chounan, Y.; Horino, H.; PI1
BuTe
BuLi , TI-IF , -78°C Dahdouh. M.J.; Jacoh, R.G.; Ferreira, J.T.B.; Dahdouh, V.B.; Marques, F. de.A. Tetruhedron Lxtt., l Y Y Y , 40, 7159.
70
Compendium of Organic Synthetic Methods, Vol 11
,0.2SmIz,TI-IF
1.
mischmetall , 20°C
*
2. H30+
mischmetall = alloy of [La/Ce/Nd/PrGm] J. Org. Chetn.. 1999,64, 2944. IIblion, F.; Namv. . J.-L
mBr*
€el 6
Ph
In , H 2 0 , rt , overnight
Ph
Section 44
90%
Yung, Y. J. Atit Cheni. Soc., 1999, 121, 3228.
;-
REVIEWS "Arylationwith Organolead and Organobismuth Reagents,' Elliott, G.I.; Tetruhedron, 2001, 57, 5683. "CatalyticAsymmetric Organic Zinc Addition to Carhonyl Compounds,' Chem. Rev., 2001, 101, 151.
u; Yu, H.-B.
SECTION 43: ALCOHOLS AND THIOLS FROM NITRILES NO ADDITIONAL EXAMPLES
SECTION 44: A1,COHOLS AND THIOLS FROM ALKENES 1 . B I I ~ * S M ,CTHF ~ , 0°C -s I t 2. NEt3 , catechol, 0°C ,0°C + 12
4 3.02,1t,12h
-
Ph
+
Ph-Orl
li:
Ph
1)
(9 Cadot, C.; Palko. P.1.: Cossv. J. Tetruhedrori I x t t . , 2001, 42, 1661.
69%
1%
B.
/ -
1. MeN>
-
,toluene, 18 h
1.6%J Cp2*Sm-TI IF 2. NaOII ,11202
Molander. G.&; Pkilfcr, D. Org. L t q 2001, 3, 361.
p
*-OH
* A
v-
86%
Section 44
Alcohols from Alkenes
1. BH3, TIIF , 9 0 ° C , 1 d 2. I120z ,NaOH
%-
71
OH
H Ph Varela, J.J.; Peiia,
D.;Goldfuss, B.; Polhorn, K.;Knochcl. P. Org. Lett., 2002, 3, 2395.
l.chiralAlcatalyst,DCM,rt 2. 2.5 BF?.OEt2, DCM q
o
B
46%
n
SH
3. 3rrqHSCII,CH,SH t,lh
DCM,rt,lOh
phu= -x
Nishide, K.; Ohsugi, S.-i.; Shiraki, H.; Tamakita, 11.;
/
3 eq TiC1, , toluene , 0°C
-
Org. Lett., 2001, 3, 3121.
P
h
a
1 , 2 x I = = S ,U.SCu0,1 h
Mukaiyama, T.; Saitoh, T.; Jona, 14. Chem. Lett., 2001, 638.
A
1. 1% [Rh(cod)2] BF,, ether, DCE 1.2% bis-phosphine ligand
Ph
Ph ca tec hohorme 2.3M KOH , H20, Demay, S.; Volant, F.; fiochel. P,Angew. Chem. Int. Ed., 2001, 40, 1235.
88%
92% S
1. 20% (Cl2SnO), , 1 d 2. (Me3SiO)z , 2 TMSN3 , I X M 3. AcOH , H 2 0 Sakurada, I.; Yamasaki, S.; Kanai, M.; Shihasaki. M. Tetruldron Lett., 2000,41, 2415
2) NaOH / € I 2 0 2 Kantha, J.V.B.;Brown. H.C. Tetruhedron Lett., 2000, 41, 9361.
89% (94:6 1-:2-)
72
\+hP
Section 44
Compendium of Organic Synthetic Methods, Vol 11
2. MqSiCHN2, THF, reflux 3 . H 2 q , NaOH 4. Bu4NF, THF
) .
OH
Ph 60% overall
Goddard, J.-P.; LeGall. T.: Mioskowski. C. Org. Lcrtt., 2000, 2, 1455. 1. S% [l, lO-phenmthndinePdM~Cl] HSiMe20SiMe3 , DCM ,-20°C
2. KF , M e C q H , rt , 2 d Pei, T.; W'den o e i :
.A, Org. Lett., 2000, 1, 1469. cat [Cp(TMShY( ~ - M e ) ] z
,." .'
PhSI13, cyclohexane
OH 90%(98:2 ds)
rt,6h
Molander.;Schmitt, M.11. .I. Org. Chem., 20110, 65, 3767. +,"
1 . TIIF, NiBII, 2. BF,*OEt,, 'IIIF, 0°C
,#'
3 . 1 1 2 0 ,rt , 2 h * QOH 4. Oxone, H 2 0 , 0°C -+ rt . . Rlnln.;Cai, W.; Brenek, S.J. Tetruhedron Lett., 2000, 41, 5817. 1. HSiMe20TBDPS, DCM -20°C , 12 h
2. TBAF , K F , K H C O 3 , TIIF SO% H 2 0 2 , rt , 3 d Pei, T.;
Tcrrulztdron Lett., 2000, 41, 7597. 1.
MazC
99 ~ 4 8 %( S O : de) 90%ee
, hexanes mBBn2 O"C, 2 h
2. r1202 , N ~ O I I
.A Org. Lett., 1999, 1, 485.
Me
Section 45A
SECTION 45:
Protection of AIcohols
73
ALCOHOLS AND THIOLS FROM MISCELLANEOUS COMPOUNDS 30% HzOz, HZO B(OW2
Simon, J.; Salzhrunn, S.; Prakash, G.K.S.; J. Org. C h m . , 2001, 66, 6 3 3 .
85%
; Olah, G.A.
In , NH4Cl, EtOH ,reflux, 2 h BnS-SBn * BnSH v. G.V.S*.; Rao, G.V.; Ivenear. D.S Synth. Cominun., 2000, 30, 859.
97%
'L
ZlC14, NaBH4, THF PhSSPh * PhSH Chary, K.P.; Rajaram, S.; Ivencar, D.S. Synrli. Comnzun., 2000, 30, 3905.
95%
B&em yeast, S U C ~ O S ~ H ~ O Ph
EtOH ,3O"C, 2 d
OMe Ferrahoschi, P.; Reza-Elahi, S.; Verza, E.; Tetruhedron A syntm., 1999, 10, 2639.
* PhL
o
.
82% (>98% ee)
SECTION 4SA: PROTECTION OF ALCOHOLS AND THIOLS
\
TI IF 83% .01M MeCN , hv (254 run) , 3 0 min
M.C.; Fallon, L.; Zhu, J.; Lee, Y.R. J . Am. Chent. Soc., 2001, 123, 3638.
74
Section 4SA
Compendium of Organic Synthetic Methods, Vol 11
OAc
I
OMEM 10% CAN, A q O , 1 d
m u m . K.; Suzuki, T.; Nishida, Y.; Satsumahayashi, K.; Horaguchi, T. Chem. Left., 2001, 1012. dihydmpyran ,1 2 , THF
78%
microwaves, 150 sec ,67"C
aoMoM J. Org. Chmi., 2001, 61, 1947.
Deka, N.;
Montmorillonite K10 DCM , r t , 3 h
C€IO . I . Deville, J.P.; -
kOIl
Ph
vows CHO
Orb'. Cliern., 2001, 66, 4097.
Ph
TMSN3, TBAB , neat, 2 h
*
96%
cq
Amantini, D.; Fringuelli, F.; plzzo.; Vaccaro, L. J. Org. Chem., 2001, 66, 6734. AczO , Bi(0Tfh ,TIIF
*
rt,4h 0II OAc Orita, A,; Tanahashi, C.; Kakuda, A.; Qtera. .I, J. Org. Chenz., 2001, 66, 8926.
93%
97% Sahitha. G.; Bahu, R.S.; Rajkumar, M.; Srividya, R.; Yadav, J.S.Org. Lett., 2001, 3, 1149. n
FimcI-IN
o
9
N
C02Me
G6rnez-Vidal, J.A.; Foirester, M.?'.;
o
2
5 q N a N 3 , MeOH 3.5"C114 h
Fm,cHN
9.5% + methylp-nifrobenzoate Orb. Lett., 2001, 3, 2477.
Section 45A
75
Pmtection of Alcohols
lO%Yb(OTf), or FeQ3 Ph2CHOH, CHzClz ,30min
*
Ph Ph 87% Shiuma. G.V.W; Prasad, T.R.; Mahalingam, A.K. Tetruhedron Lett., 2001, 42, 759. kaolinilk clay , MeOH
-+ PhAH 96% 2 5 T , 20 min Bandgar. R.P.; Uppalla, L.S.; Sagar, A.D.; Sadavarte, V.S. Tetmlierfron Zxtt., 2001, 42, 1163.
Ph 4 A c
01I
Ph
Solis-oha, A,;v-
.
. T,;
62% 5% Koroniak, L.; Frey, D. Tcrruhedron Lett., 2001, 42, 1241.
*
Br2, MeOH ,reflux, 1 h
L
O
H
94%
Barros, M.T.; Maycock, C.D.; Thomassigny, C. Synlett, 2001, 1146.
OH
DHP ,silica chbride , rt
82%
30 min
Ravindranath, N.; Ramesh, C.;
*
Synlett, 200Z, 1777. KF/Al203,
B
r
\~ O /T
B
D
M
Bl .d ..ss.;Hailis, C.L.; Portlock, PhCI42OII quant
S
DME
4h
-
H O-&
\ /
D.E. Ti,truhc~fronLett., 2001, 42, 1611.
~ ~ - ,~5 min DIIP , K & O W , ~ O IIzO
+
PhCHzOTHP
92%
97%
M L S H , K5CoW12040*3H 2 0 , 1 h , rt Hahihi. M.H.; Tangestaninejad, S.; Mohammadpoor-Baltork, I.; Mirkhani, V.; Yadollahi, B. Tetruhcdron Lxtt., 2001, 42, 2851.
76
Compendium of Organic Synthetic Methods, VoI 1 1
n
Ax
21
Py((HF), , MtCN
Section 45A
81% Ph Watanahe. Y.; Kiyosawa, Y.; Tatsukawa, A.; Hayashi, M. Tetruherfron k t t . , 2001, 42, 4641.
r
Ph
*
20min,rt
AczO, 5% Cu(OTf)z, rt ,2.5 h
*
Ph
75%
Ph
ROSiR3 is convertcd to ROAc Chandra, K.L.; Sxavanan, P.; & w h . V.K, Tetrahedron Lett., 2001, 42, 5309. PhQ"-
-
PhO -H
74%
\ / *
NaH,THF,O"C, I d DDA , H,O/CH,CI,
,
Ph
5h
65%
Sharma. G.V.M.;Rakesh Tetrulwdron Lxtt., 2001, 42. 5571
In ,
NHdCI, MeOH 30 min
OBz
0
0EI
OBz
98% Valluii, M.; Mineno, T.; Hindupur, R.M.; Averv. M.A. Tctruhedron Lett., 20UI, 42, 7153
phO -" 95%)
-
-
DIIP, DCM , Bu4NBr3 ,rt
OTHP
PI,-
87%
BudNBr3, MtOH , rt Naik, S.; Gopinath, K.;Patel. B.K. Tetruhedron Lett., 2001, 42, 7679.
QJ,:, -A NloT Nd JJorq Me
I
NO,
a2Me D N@ C M ,Me Ir t , 1 h
BnO
91
I1
%I
Loudwig, S . ;
Bn0
1
II
hv , aq EtON Tetmheilron Ixtt., 2001, 42, 7057.
COzMe
88%
Protection of Alcohols
Section 45A
a L Y
EtO2C
Hz ,W I C Et0I-I
OTHP
j
77
E
t
0
-
,
C
O
O
\
H
quant
Kaisalo.; IIase, T.A. Tetruhcdron Lett., 2001, 42, 7699. CBr4, i - R O H , reflux
PhCH,oH 2.5 h Lgg. A.S.-Y.; Hum, Y.-.I.; Chu, S.-F. Tetruherlron, 2001, 57, 2121. PhCX1,OMOM
91%
polymethylhydmsiloxane
Ph - O 7 I
ZnC12/Pd(PPh3)4, THF , It
PhO -H
Chandrasekhar. S.; Reddy, Ch.R.; Rao, K.J.TetruherIron, 2001, 57, 3435. P hCI 1,OH Branco, L.C.; B uOCP h,
DIIP , T P P , IIBr
94%
PhCH20TIIP
/
96%
[bmim] BF4 Tetruherlron, 2001, 57, 440.5. 0.1 Ce(OTf)4 , wet MLCN
-
BuOiI
87%
rt,2h W f i - N e z h a d . A;; Alamdari, R.F. Tetruherfrorr,2001, 57, 6805. PhCH2OH
A d 1 , n e a t , Kl-AI203
* PhCH20Ac
95%
4 min
J’adnv.
V.K.; Bahu, K.G.; Mittal, M. Tctrulzerlran, 2001, 57, 7047.
I’ hCH201I
S% K ~ C O W I ~€ O 1 2 0~ ~ * ~
t PhCI1,OAc 94% EtOAc , reflux , 3 h ; Tangestaninejad, S.; Mirkhani, V.; Yadollahi, B. TetruhPdron, 2001, 57, 8333.
1.6
\ /
c*o&=(-o‘* I.
P h-om Suzuki, T.;
K2C03, NMP 100°C. 3 h
-
a; Sharme, I>.; Sharma, 17. Tc.trrihedron,2001, 57, 9343. 1 . THPOAc. 5% TBS-OTf EtCN , -7i(”C, 1.5 inin
2. 10% Et3N, -78”C, 5 inin
. Synthesis, 2001, 555.
* Ph-0THp 96%
78
Section 45A
Compendium of Organic Synthetic Methods, Vol 11
1.5eq A c 2 0 , MeCN , 25 inin Ph-OH
0.1 Bi(OTO3.x H2O Carrigan, M.D.; Freiherg, D.A.; Smith, R.C.; Zerth, H.M.; Syntltesis, 2001, 2001.
4'
b&n
82%
OH 60%
Org. Lett., 2001, 3, 2835.
AcOII , P 2 0 5 , S i 0 2 , rt
60%
u; C6H13011
c 88%
* ph4Ac solid state , 6 h Rafei, M.: Karimi, M.H. Synth. Comnnzun., 2001, 31, 771.
P h 4 H
A
Brio BnO
0
Kitov, P.I.; &,&-Q&
O
3 eq N M O , OsO, , aq dioxane 2 eq aq N d O , , 60"C, 18 h
w
BnO B n 0
w Ph
*
(TMShNH , inicmwaves , LiClO, F
+
C6H,,0TMS
-83%
rnicmwaves , clay, H 2 0 Bandrar. B.P.; Kasture, S.P. Monat. C h m . , 2001, 132, 1101.
InBr3, aq MtCN
BnOO -Tr
heat. 2.5 h
*
P BnO
O
H
90% yadav. J.S.;Reddy, B.V.S.; Srinivas, R.; Maiti, A. J. Chern. Rex (S), 2001, 528. BiC13 , MeOII, rt , 2 inin P hCI I2OTMS * PhCHzOH 97% Firouzahadi, H.; &&iminad_noor-Baltork. I.; Kolagar, S. Synth. Cornrnun.,2001, 31, 905. PhCH20H ;-
Ac20 , microwaves, 8 min
* PhCHzOAc Kasture, S.P.; Kamhle, V.T. Synth. Conintun. 2001, 31, 2255.
80%
TBDMSCl,DCM,rl chiral quinidine hase
OH Isohe, T.; Fukuda, K.; Araki, Y.;
SO% ( 39% ee) OTBDMS
Clwnz. Contnzun., 2001, 243.
Section 45A
PhCHZOTHP
Protection of Alcohols
Sc(OTf), , MLCNIMLOH
.
79
*
PhCH2OH
84%
also with ROMOM It Watahiki, T.; Kohayashi, Y.; Hirano, H.; Suzuki, T. Synth. Coniinun., 2001, 31, 2305.
;.T-
HC02CI-IPh2 , E4SiH
-0THP Ph
OCHPh2 * PhTMSOTf , silica gelh4eCN 90% 0°C. 1 h Suzuki, T.; Kohayashi, K.; Noda, K.; Orivama. T. Synth. Continun. 2001, 31, 2761.
In
P hCI IZOTHP
,I2 , EtOAc
, reflux, 1.5 h
* PhCHlOAc
also with RMOM Ranu. B.C.; Hajara, A. J. Chein. Snc., Perkin Truns. 1, 2001, 355. Ranu. B.C.; €Iajra, A. J. Chern. Soc., Perkin Truns. 1, 2001, 2262.
80%
Ph,SiH, Korr , 18-crown-6 DCM ,rt
87%
OSiPh3
T.; IICnique, J.; Samuel. E. Chent. Connnun., 2001, 1408.
orr I
PhN=C(Ph)O'IBDPA ,THF
PhA C 0 , E t Misaki, T.; Kurihara, M.;
P hCr 1 , o n r P
OTBDPS
I
*
99%
rt , 3 0 m i n Ph4 0 2 m Clienz. Continun., 2001, 2478.
NH4+ C Q C r , Montmorillonite K10 microwaves, 20 sec
*
PhCHO
94%
Heravi. M.M.; Hekrnatshoar, R.; Beheshtiha, Y.S.; Chassemzadeh, M. Monut. choni.,2001, 132, 651.
orr &C02Et
cJNQ OPMP
, 1.1%Me3SiOTf
DCM, r t , 0°C
Nakano, M.; Kikuchi, W.; Matsuo, J.-i.;
P hCH,OA c
&&C02Et Cheni. Lett., 2001, 424.
10% P( 2,4, 6-trimethoxyphenyl)3
MeOH,5OoC,3 h Yoshimoto, K.; Kawahata, 11.; Nakamichi, N.; JTavashi.
--
QpMp
t
PhCH20H
Chern. Zxrr., 2001, 934.
91%
90%
80
Coinpendiuin of Organic Synthetic Methods, Vol 11
-
1.2 eq BnOMs, 10% LiB(C6F5), LiOTf , 1.6 eq MgO ,it, 1 d
a 0 1 4
cyclohexane-DCM
Section 45A
c1M
O
.
Oxone, MeCN ,reflux, 5 h
.
*
n
97%
Nakano, M.; Matsuo, J.-i.; Mukaiyania, T. Chcm. Lett., 2000, 1352. P hCIIzOSiMq
B
99%
PhCH20H
/\mini, M.K.; Farshidipoor, S. Bull. Cliein. Snc. Jpn., 2000, 73, 2775.
; -
r 2% Sc(0Tfi
Ph
EtCN.. rt .. 30in Suzuki, T.; Wntahiki, T.; Orivama. T. Tm-uliedron Lett., 2000, 41,8903.
88%
ph
EDC, B oBO DMAP, H DCMt-
L
o
C::
Clark, M.A.;
;.T-
1
1
-
o
0
90%
. .
y
B
n
-
96%
€I2,10% Pd / C , EtOAc Tetruhedron L.ett., 2000, 41, 9523. 40% DIIP , SM ~lq Nd3S04
93%
toluene, 30"C, 50 inin
I-Iayakawa, S.;IIirasaka, Y.; Saitoh, M. Tetvuhedron Lett., 2000, 41, 9843.
Mn(0Ach - DDQ
O~MB
n
75%
CHzCl2, rt , 8.Sh
OH
n
Sharma. G.V.M.: Lavanya, B.; Mahalingam, A.K.; Krishna, P.R. Tetrulz~rirnnLett., 2000, 41. 10323.
Section 45A
Protection of Alcohols
81
Iwasaki, F.; Muki, T.; Onomura, 0.;Nakashima, W.; Matsumura. J. Org. Cheni., 2000, 65, 996.
Y,
DMSO, 80°C , 3 6 h Ph-o?-sDMs
* Ph-OH
,P c NMe MeNMeN \
CN23
O3
90%
Yu, 2.; Verkade. J.G. J. 01-g. CIieni., 2000, 65, 2065.
BnOH , BiBq ,CCl,
7
77%
t
OH rt,9Gh OBn Bover.B.; Keramane, E.-M.; Koque, J.-P.; Pavia, A.A. Tetmkedron Lett., 2000, 41, 2891. CKl, , TIIF, cc1,
PhO -H
It
Ph
*
-
O
Y
s
90% Baati, K.;Valleix, A.; Mioskowski. C.; B u m a , D.K.; Falck. J.R. Org. Lett., 2000, 2, 485. Ac20 , Nation-II , rt , 3 h
Kumareswaran, R.; Pachamuthu, K.; Vankar. Y.D, Synlett, 2000, 1652. CSI-I, 10 --
1. t-BuLi , pentane , -7X"C
2. H30'
4
It
*
99%
CSHll-OH
92%
W.F.; England, M.D.; Mealy, M.J.; Thogsomkleeh, C.; Teng, L. Org. &It., 2000, 2, 489. V.
1. BU3SnII, AIBN , PhH 0.0SM d O S i P h 2 S i M e 3
2. MeLi
Studel.;Bossart, M.; Vasella, T. Org. Lett., 2000, 2 , 985.
_.
82
Section 45A
Compendium of Organic Synthetic Methods, VoI 11
Ph
OBn
3% Sc(NTf,), , anisole lOO"C, 2.5 h
-
-OH
--
Ph
92%
Ishihara, K.; Hiraiwa, Y.; Yamamoto. H,Synlett, 20'00, 80. M t O H , 30°C, 19 h H
+,
ph-oH
93%
0
Cl(Bu)2Sn( ;Sn(Bu)zCl 0
H Orita, A.; Sakamoto, K.; Hamada, Y.; O t e r a . S y n k t t , 2000, 140.
PhO
w
Et2NH , Pd(OAc),, TPFTS
+ PhOII (+ allyldietbylamine) sec-( 2,6di-O-methyl)- f3-cyclodexfrin quant
Widehem, R.; Lacroix, T.; Bricout, H.; M o n f l i e r . S y n l e t t , 2000, 722. 3 eq Mg , 3 eq Me,SiCl
OSiMe3 DMF, rt p+ . . Nlshltuchl.;E t a , Y.; Watanahe, M.; Ishino, Y.; Ohno, T.; Maekawa, H. Synlett, 2000, 1025. P
,
i OH
h
99%
I
92% (100% ee)
Yadav. J.S.; Reddy, P.T.; Hashim, S.K. Synlett, 2000, 1049. 20% TiCl4, X M , A ~ 2 0
I'h -onw ;-
I
..
O"C+ r t , 6 h
,
P hCI I,OH 83%J -
OAc * PhM
78% Ramachandar, T.; Reddy, M.V.; Takhi, M. J . Org. Chem., 2000, 65, 4729. dihydmpyran , cat I,, DCM , 3 0 min
t
Ph a 2 - O T H P
MeOH, 12, heat, 3 h Kumar. 1I.M.S.; Reddy, B.V.S.; Reddy, E.J.; Yadav, J.S. Che171. Lett., 2000, 857.
90%
-
Section 45A
Protection of Alcohols
OPMB
83
CBr4, MtOI-I, reflux , 6 h Ph-OH
Ph
Yadav. J.L;Reddy, B.V.S. Chem. Lett., 2000, 566.
OH
-
0.5 DMAP , rt
p-Tol-Cl120CPh,, MS 4A
-0"
97%
5 eq pyrmlidine , THF , BuLi
rt, 16h h i m , X.; Costa, A.M.; Faja, M.; Pine&, 0.;
Ph
87%
DPQ , DCM ,i t , 2 0 inin
Cqt-Bu Org. L ~ t t . 2000, , 2, 2809.
* Ph
Sharma. G.V.M_; Mahalingam, A.K.; Prasad, T.R. Synlett, 2000, 1479.
96%
Bahwa. J.S.; Vivelo, .I.; Slade, .I.; RepiE, 0.;Blacklock, T. Tetruhedron Lett., 2000, 41, 6021. 3 eqBiCl,, 2,4,6-~llidine
C,% -OH
QO
t
c7111S
,6O"C , add over6 h
Barks, J.M.; Gilhert, B.C.; &sons.
-0 88%
U ;Upeandran, B. Tetruherlron Lett., 2000, 41, 6249.
TIPSCl ,imidazole ,micmwavas PhCHzOII t PhCH2OTIPS K h,J .l J f-i ~ t z h a d&; . Alandmi, R.F.; Zekxi, N. Tctrulzedmn, 2000, 56, 7503. 1
C,,,H,,OSEM
10 eq MgBr2/ether/MeN02
-
~loHzloH
Vakalopoulos, A.; Hoffinann. FI .M.R. Org. Lxtt., 2000, 2, 1447. Zr - sulfophenyl phosphonate
* MqCCHGAc AczO, D C M , rt , 15 h . . Cunnl.;Epifano, F.; Marcotullio, M.C.; Rosati, 0.;Rossi, M. Synth. Conzl,lltn., 2000, 30, 1319. MqCCHzOI-I
96%
99%
74%
Compendium of Organic Synthetic Methods, Vol 11
84
Section 45 A
--
92% Yu, W.; Su, M.; Gao, X.; Yang, Z.; .lin.Z. Tetrultedmn Lett., 2000, 41, 4015. DHP, DCM ,Z C l , O -H
OTHP
*
96% MLOH, Z r C l 4 Rezai, N.; Meyhodi. F A . ; &l&iJL Synth. Coniniun., 2000, 30, 1799.
air, Co or Mn salts PhCN,OS i Me, c PhCH,OH )I,J . sheml.;Kalantari, P. Synth. Commun., 2000, 30, 1857. AcOII , La Y-zeolite
PhCH,OI-I
Narender, N.; Srinivnsu, P.; OTH P
I
A
c
94%
80%
PhCXI2OAc
99% 116"C, 8 h ' ' I ; Raghavan, K.V. Synth. Conmzun., 2000, 30, 1887. 01.1
CuCl2.2 If20 ,MtOH z
I ) ,
85%
Ph rt,lh Ph Davis, K.J.; Bhalerao, U.T.; &>. B.V, Synth. Commun., 2000, 30, 2301. ~
~~
Pansare. S.V.; Malusare, M.G.; Rai, A.N. Synth. Commun., 2000, 30, 2587. NaCNBH3 ,MeCN
TMSCl Rao, G.V.; Reddy, D.S.; Mohan, G.11.; w a r . D.S . Synth. Commun., 2000, 30, 3565. PhC€I,OII 89%
-
DIIP, LiBr , DCM
*
LiBr , MeOH ,heat Reddy, M.A.; Reddy, L.R.; Bhanumathi, N.; Rao. K.R. Synth. Commun., 2000, 30, 4323.
Section 45A
Protection of Alcohols
85
C~C13.7H20 , M d I i
PhCH20TIIP Reddy, G.S.; Neelakantan, P.;
* PhCH,OH 30 min D.S. Syntli. Coninum., 2000,30,4107.
90%
PH ZdKPO,), , aq acetone 6O"C, 7 h
Me02C Me02d 79% Curini. M .; Epifano, F.; Marcotullio, M.C.; Rosati, 0.;Rossi, M.; Tsadjout, A. Syntli. Comiirrin., 2000, 30, 3 181. DHP ,cat I,, miaowaves , 7 min
PhCH,OII
91% -.
PhCH,OTIIP
D 4
84% M d H , cat I , , microwaves, 10 inin Deka, N.;Sarma. J.C, Synth. Commun., 2000, 30, 4435.
MrCN , Nd , Me3SiC1
*
2h
Kdmdl.; . . Laxinan, E.; Rao, N.V. Tetrahedron
&ti., 1999,
+OH 98%
40,371.
OSiMqt-Bu t-BuMqSiO
0.1 Nal
t;" u M q S
i
0.1 M MeCN 0.2 TMSCI/H,O Gricco. P.A.; Markworth, C.J. Tetruhcdron Lett., 1999, 40,665.
O
d
o
H
/ 86%
CBr, , MeOH, reflux , 3 h -0mp Ph * PhO -H Lee. A S - Y . ; Su, F.-Y.; Liao, Y.-C. Tetruherlron Lett., 1999, 40, 1323.
91%
Zn@F4h, H 2 0 12 h A. Tetruhedron LL'tt., 1999, 40,1985.
87%
Coinpendium of Organic Synthetic Methods, Vol 11
86
OH I
-
AczO ,CHzCIz , 3 0 min
I
A
Section 45A
-
OAc
I I
A
92%
2.5% C ~ ( 0 T f ) z Ph Tetruhcdron Lett., 1999, 40, 261 1.
Ph Saravanan, P.; &&lJL,K
3% C A N , 70°C ,MeCN CdJI 1- 0 n I P
*
pH 8 borate buffer
OH
C5H11
94% Markti. I.E.; Ates, A.; Augustyns, B.; Gautier, A.; Quesnel, Y.;Turet, L.; Wiaux, M. Tetruiicrirnn LtK, 1999, 40, 5613. e- , PdClz-bipy , DMF, B u P B F ~
PhOCI I ?CH=CII2
*
PhOH
75%
Franco, D.; Panyella, D.; Rocamora, M.; Gomez, M.; Clinet, J.C.; Trtrultedron Lr.tt., 1999, 40, 5688.
* ’\
CeC13*7Hfl,M&N
NaI , rxflux , 6 h
Thomas, R.M.; Reddy, G.S.;
’
BzCl , TMEDA , MS 4A
Ph CHzClz ,-78°C , 2 0 min Sano, T.; Ohashi, K.; Orivaina. T. Synflmis, 1999, 1141
-
>
cat B(C&),
I’h -OH
/J
97%
C
O
\ /
O
H 94%
J . Org. Chein., 1999, 64, 4211. , Ph3SiH , toluene
rt,20h Blackwell, J.M.; Foster, K.L.; Beck, V.H.; PhOAc
-
Ph
electro-generated Ni , AcONa* N D M F , 18 h , r t
YdbUhdld.; , . ... Kasano, A,;
90%
Tetruherlron Lxtt., 1999, 40, 7293.
* Ph
93% W E, J . Org. Chem., 1999, 64, 4887.
PhStI , S % KzCO,, NMP
PhOH reflux, 15 min ; Nayak, M.K.; Shanna, L. J. Org. Chcin., 1999 64, 8027. /
96%
Section 45A
Protection of Alcohols
4
Ph
V$l,
~
~
~
~
a7
,
Ph +OMPM , 4 80% h
*
g
Mahalingam, A.K. J. Org. Chcm., 1999, 64, 8943. CH,=CHOAc, THF , 1 7 h
-H PhO
Ph
B nN=P( NMe&
Ilankulnaran, P.;
99%
w.J.G. J. Org. Cheni.,1999, 64, 9063. Oxone, 58%
‘y-l
MLOH
*
B nO-(CI12k-OTBDMS
3h Sdl. . . G.; Syamala, M.; Yadav, J.S. Org. Lm.,1999, I , 1701.
,’
P hCH,OTI IP
K- 10 Montrnorilbiiite clay
MLOH,rt,Ih Tankguchi, T.; Kadota, K.; El Azah, AS.;
OAc
90%
BnWCH2)r-OH
*
PhCH2OH
91%
Synletf, 1999, 1200.
AcOII ,at FeCl3 , 1 h
* Ph o -*c
O H -hP
99% V.M.; Mahalingam, A.K.; Nagarajan, M.; Ilangovan, A.; Radhakrishna, P.
Synlett, 1999, 1200.
&mfy.
CJ,; Pitts, M.R. Synleft, 1999, 1575
P hCH20H Chauhan, K.K.; o-Ac Ph
O.l%In(OTfh, MeCN ,rt
w PhCH20Ac A%?O Love, I.; Waite, D. Synlett, Z999, 1743.
97%
u;
i-PIOII, =flux, 12 h 10% Yb(OTQ3
Sharina. G.V.M.; Ilangovan, A. Synlett, Z999, 1963.
-
H PhO 95%
88
Compendium of Organic Synthetic Methods, Vol 11
Section 45A
90% hv ,MeOH 85% Brook. M A; Balduni, S.; Mohamed, M.; Gottardo, C. T&-uhedron,1999, 55, 10027. Montmorillonite K10, MeOH CH€Il 7 4 T H P
50°C J.i. T.-S.; Zhang, Z.-€l.; Jin, T . 3 . Synth. Continun. 1999, 2Y, 181. cil t
C8H174H
(y0m;5
a - Z O3 ~ PMe)l .2( O3FC6H4S03H)a .x DCM , TMSZNII ,rt
- .0. O ”
*
; Epifano, F.; Marcotullio, M.C.; Rosati, 0.;Costantino, U. Synth. Conintun., 1999, 2Y, 54 1.
DHP , H2S04 , S i 0 2 , 1 inin PhCH2OI I
+
P hCH2OTHP
4
90%
H2SO4, S i O z , MtOIf , reflux , 15 min
92%
--w9
.Huiw-MX; Ajami, D.; Ghassemzadeh, M. Synth. Coininun., Z999, 29, 1013. 1
.
DIfP , SnC12*2H 2 0
*
Davis, K.J.; Bhalerao, U.T.; B;w. B.V. Syntfi. Coniniun. 1999, 2Y, 1679. TiCI, , EtOAc, 0.85 h PhCH20TMS + €ranpoor. N.; Zeynizadeh, B. Synth. Coniniun., 1999, 29, 2123.
PhCI120Ac
..
89%
PhBF?K, 5% Pd(0Ac)z , DME
* Ph-Ph 99% 60°C. 1 h 4dlltha.; ‘. ,’ Reddy, B.V.S.; Srividya, R.; Yadav, J.S. Synth. Comniun., 1999, 29, 2311. Ph21+BF;
PhCH2 OT HP
Clayan , N114N03 , 3 min
w PhCHzOH miaowaves Me . h .. hldm.;Sumitra, G.; Raddy, G.S.; Ganesh, Y.S.S.;Yadav, J.S. Synlh. Conimim., 1999, 2Y, 2807.
90%
MeOIi, DCM , LBF, C& ,7-OC:Phh2 Ar =p-nlethoxyphenyl
McCN
CJl174H
Chen.;Zheng, Y . ;Zhou, X. Synth. Conimun., 1999, 29, 3421.
94%
Section 45A
Protection of Alcohols
89
-
MOM-Br , NaOMe , DMF
rt , 3 0 m i n
;-
B
r
~
O
\ /
also with ArOSiK3 Noda, K.; Sugawara, S. Synth. Coilitnun., 1999, 29, 2217.
M
O 85%
93% Kajiro. 11.; Mitamura, S.; Mori, A.; fIivama. T. Bull. Chern. Soc. Jpn., 1999, 72, 1553. Ph-OTM S
a t PdCI,(PhCNk, 3 inin
Ph-OH
(also with Montinorillonite K10 , 1min) - quant Mojtahedi, M.M.; &,&-MJL ; Heravi, M.M.; Bolourtchian, M. Monnt. Chcvii., 1999, 1-30, 1175.
qumt
M
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 4 PREPARATION OF ALDEHYDES
SECTION 46: ALDEHYDES FROM ALKYNES
-
C6HI3
2% RuCpCl(dppm) , H 2 0 , 12 h
Suzuki, T.; Tokunaga, M.;
P h =
* C6H13CH2CHO
93%
, i-PlOH, sealed I u ~ 100°C ' Org. Lett., 2001, 3, 735.
1. 5% [ R u ( T ~ ' - C ~ H ~ X P P ~, H2O ~)C~] i-PrOH ,90"C , 2 d * Ph-CHO 2. "1C ~ ~ H 2 ~ S O ~ - N i i + 3. aq. C16H38NMq+Br71%
i-
,( i
Ph
Alvarez, P.; Bassetti. M .: Guneno. ' J .; Mancini, G. Tetrahedron Lett.,2001, 42, 8467.
17%
SECTION 47: ALDEHYDES FROM ACID DERIVATIVES
Ph
Ll
cat InCI3 , Bu,SnII ,toluene
0.2 PPh3 , -30°C , 2 h
Phl
H
97%
Inoue, K.; Yasuda, M.; Shihata, I.; Baha. A. Tetruhedron Lett., 2000, 41, 113.
8,
1. AlH, * 2. PCC Bu Bu Cha.;Kim, J.M.; Chun, J.H.; Kwon, 0.0.;Kwon, S.Y.; Han, S.W. Org. Prep. Procced Int, 1999, 31, 204.
h PhCHO 3. P c c Lee, D.Y.; Kim, J.M. Org. Prep. Proceed. Int., 1999, 31, 694.
PhCO,H
C2hrd.L;
1. NaBIl4 2. M%S04
95%
82%
Section 48
Aldehydes from Alcohols
91
SECTION 48: ALDEHYDES FROM ALCOHOLS AND THIOLS P hC€I,OH
Pd(II)-hydrohlcite , toluene, air
t PhCH0 98% 0.2Py,65"C,3 h Kakiuchi, N.; Maeda, Y.; Nishimura, T.; J. Org. Chem., 2001, 66, 6620.
PhCH20H
DMSO, T H F ,-30°C
B-
PhCHO
91%
4 N-("
N
De Luca, L.; Giacomelli. &; Porcheddu, A. J. Org. Chcm. 2001, 66, 7907.
\
PhCH,OH Fey, T.; Fischer, €1.; Bachmann, S.; ALhert, K.;
75%
PhCHO
t
J. Org. Chem. 2001, 66, 8154.
1% Hg[PM010VZ040] ,TEMPO C6rh 3
C,H,,/\CHO
O2 (2 atm) , acebne , 100°C
Ben-Daniel, R.; Alsters, P.; N e u m a U J. Org. Chern., 2001, 66, 8650.
CI-N
L? k
0
O H-
98%
)=O
N\
C1
CHO
0.1 TEMPO, DCM , rt
De Luca, L.; Giacomelli. G.; Porchedda, A. Org. LEtt., 2001, 3, 3041. [(ANS-O)2Bi - 0 1 ,
CIOHZIOH
rt , 5 min
, CH2C12
*
Matano. Y.; Nomura, H. J. Am. Cheni. SOC., 2001, 123, 6443.
C&I,,CHO
96%
96%
92
Section 48
Compendium of Organic Synthetic Methods, Vol 11
Schlenk tube, h4S 4A
* C5HllCHO Bu,NIO, , toluene, 60°C 1 d Khan, F.; Singh, N.; van Staden, M. Synbtt, 2001, 869.
C ~11 ~I 1 1 ~ 0 1 1
.
.
plymer--C6H,--CI12-X1
quant
20% TPAP
* PhCI-IO 93% MS 4 A , CH2C12,rt X = NMO Brown, D.S.; Kerr.;Lindsay, D.M.; Pike, K.G.; Ratcliffe, P.D. Synlett, 2001, 1257. PhCII,OII
PhCH, OH
phosphate buffered Si&-suppited
KMn04 t
PhCHzPPh3+ 10,- , AIC13/MeCN
P hCH,OH
*
flux, 1.5 h
99%
PhCHO
cyclohexane , 6 5 T Yakernoto, T.; Yasuda, K.; h v . S.V.Synlctt, 2001, 1555.
PhCHO
78%
Samimi, H.A. Synlett, 2001, 1735.
; -
TEMPO, 0 2 ,cat Mn(N03),
C,H,,CH,OH
C6H13CH0
t
AcOII ,cat Co(N03h , 40°C, 6 h
93% Cecchetto, A.; Fontana, F.; Minisci. F.; Recupero, F. Tetruhedron Lett., 2001, 42, 6651. 2% Ru complex, rt 0
2
N
e
O
H
hv , air, toluene, 1 d
-
O
2
N
G
C
H
quant
Miyata, A.; Murakaini, M.; hie, R.; b t s u k i. T, Tetruhedron k t t . , 2001, 42, 7067. PhCI1,OII
TEMPO, laccase, H 2 0
=
PhCHO
92%
pM 4.5 , 1 d
laccase = multicopper oxidase Fahhrini, M.; Galll.;Gentili, P.; Macchitella, D. Tetruhedron Lett., 2001, 42, 7551. PhQ 12OH
PCC , no solvent, rt 15 min
-
PhCHo
Salehi.;Firouzahadi, H.; Farrokhi, A.; Gholizadeh, M. Synthesis,
.. .
4 eqCe(N03hBI03 , MeCN
96%
2001, 2273.
t PhmO 92% reflux, 2.5 h Tajik, H.; Aliakhar, A.; Akhar, A. Synth. Commun., 2001, 31, 767.
P hCM,OH
0
Section 48
Aldehydes from Alcohols
93
y-picolinium chlomchromate P hCH2OH
. .
; -
PhCHO DCM, rt Goudarzi, M. Synth. Continun., 2001, 31, 1253. +
SiOz, Jones reagent, DCM PhCHzOH Al1.; Wiggin, C.J. Synth. Conrmun., 2001, 3 1 , 1389. P hCH,OH
W n O 4 ,ZroC12-Hz0 , ether
* PhCHO *
75%
85%
PhCHO
rt ,3.5h E u u .~ d u L L ; Fakoorpour, M.; Hazarkhani, H. Synth. Conrmun., 2001, 31, 3859.
91%
Matsuo, J.4.; Kitagawa, H.; Iida, D.; M a m a . T. Chent. Lett., 2001, 150. 12
,hv,i-Pr20, 12h
c
PhO -H &oh. A.; Kodama, T.; Masaki, Y. Chem. Lett., 2001, 686.
;.T-
. . .
Matsuo, J.-i.; Iida,
m
Ph
CHO
-
95%
DCM , O T ,1 h >99% Chertt. LEN., 2001, 846.
D.;Kitagwa, H.
zeolite OMS-2, air PhCH20H Son, Y.-C.; Makwana, V.D.; Howell, A.R.; Angew. Chcnt. Int. Ed., 2001, 40, 4280.
+
PhCHO
(NH4)2Cr~07,HIO3, wet Si02
PhCHO 30 min Shirini, F.; Zolfigol, M.A.; Azadhar, M.R. Russ. J. Org. Chem., 2001, 37, 1600. P hCH20H
P hCH20H
95%
calcium hypochlorite , moist alumina
*
PhCHO
85%
87%
98%
m i m w a v e s , 1 min Mojtahedi, M.M.; Saidi. M.R,; Boloui-tchian, M.; Shirzi, J.S. Monot. Chem., 2001, 132, 655.
Compendium of Organic Synthetic Methods, Vol 11
94
Section 48
(NH,h%O, , AgN03, hexane
PhCH2OH
PhCHO 99% Montmorinonite ,60"C, 25 h Hlrdno.; Kojima, K.; Yakahe, S.; Morimoto, T. J. Chenr. Res. (S), 2001, 274. (NH& Cr207 ,XI., ,0.05 h
* PhCHO wet SiO, , solvent fm .. . Shlrlnl.; ali Zolfigol, M.; Pourhahih, A. J. Chem. Res. (S), 200Z, 476. PhCHZOH
Br*(collidiieh PF, , DCM , 2.5 h
PhCH,OH
~ o u s s e a u .G .; Rohin, S. Tetruhedron Lett., 2000, 41, 8881. cat Pd(0Ach , toluene , 8 0 T perfluomdealin ,MS 3 A . 10 h
c I I H*,CH,OH
4
*
92%
75%
PhCHO
c 11 H
* P O
76%
fluoroalkyl a e t a l pyiridine ligand Nishirnura, T.; Maeda, Y.; Kakiuchi, N.; IJemura. S. J. Clietn. Soc.,Perkin Truns. 1, 2000, 4301. PhCI 1 2 0 1 ~
;-
. ,
/
Ph-CHO
Cs2C03 , 100°C. toluene Tetruhedron Lett., 2000, 41, 7507.
Lee, M.; PhCI1,OH
5% [RuCb(p-cymene)z , O2
1.5
Ph(Cl)S=Nt-Bu. 2
DBU
+ PhCHO DCM ,-78"C, 30 inin Matsuo, J.-i.; Yanagisawa, M. Chem. Lett., 2000, 1072.
catBu4NBr,II2O2,DCM.1 d
* C,H,,CHO a t [Ru,O(OAC),~(M~OH)~] OAc Wynne, J.11.; Lloyd, C.T.; Witsil, D.R.; Mushrush, G.W.; &ikk. W.M. Org. Prep. Proceed. Int., 2000, 32, 588. C,H ISCH*OH
Barrero.; Alvarez-Manzaneda,
91%
-
98%
67%
E.J.; Chahhoun, R. Tetruhedron Lett., 2000, 41, 1959.
Section 48
Aldehydes from Alcohols
TEMPO, Oxone , rt
PhCZlO
PhCHzOH
DCM,BulNBr
Bolm.;Magnus, A S . ; Hildehrand,
95
90%
J. Org. Lett., 2000, 2, 1173.
mCHO
N i B Q , AcOH , 7 h PhO *H
* Ph 46% reflux, H$I B a n k B.K.; Ghatak, A.; Ventraman, M.S.; Decker. I.F. Synth. Commun., 2000, 30, 2701 his(1 -heiizy1-3,5,7-triaza-lazoniatricyclo[3.3 .I. i3J1 d m n e
P hCZ12OI-I
t
peroxydisulfate , MLCN
PhCIIO
98%
Minehu W.; Guichun, Z.; Zuxing, C. Synfh. Commun., 2000, 30, 3127. BnPPh3+Ci03*HCI,MeCN
PhCH2OH
*
PhCHo 85% reflux, 25 min ; Backnejad, H. Synth. Continun., 2000, 30, 3855. C Q ,70%TBHP
* PhCHO 87% microwaves, 10 inin Sineh.;Shanna, M.; Chhihher, M.; Kaur, J.; Kad, G.L. Synth. Commun., 2000, 30, 3941. PhCH2OH
pol y [vinyl@yridiniumfluoroc hmmate)]
*
PhCH,OH
PhCHO
95 %
acH
cyclohexane , rt , 15 inin Srinivasan, R.; Balasuhramanian, K. Synth. Coiiwiun., 2000, 30, 4397. OH
2% prfluornalkyl suhstituted hipyrkline , CuBr-SMe,
96% 3.5%'OTEMPO,90°C. 0, CaF18PhCI Br Betzerneier, B.; Cavazzini, M.; Quici, S.; Tetruhedron Lett., 2000, 41, 4343. P hCI 12OH
ZINO3,10% Yh(OTf), , DCM
.c PhCHO 91% x f l u x , 30 min Braddock, D.C.; McKinnell, R.M.; Waller, F.J. Synfett, 1999, 1489. W e t t . m;
NaNOz-Acg, 25°C C,HFH,OH
-
C3HFHO
60% B . P i Sadavarte, V.S.; IJppalla, L.S. J. Chem. Sor., Perkin Truns. 1, 2000, 3559. c: 1 inin
Compndium of Organic Synthetic Methods, Vol 11
96
.
; -
,
78%
microwaves, 3 min Khoee, S . Synlett, 2000, 740.
.
Th(III)-pol ypyridine complex PhCHzOH Knlle.; Frinzl, €1. Mnnat. Chem., 2000, 131, 1321. Ph
Section 48
Ru-CO-Al hydwtalcite ,Oz
OH
toluene, 6O"C, 40 min
PhCHO
c
-
mCH
Ph
89%
Matsushita, T.; Ebitani, K.; Kaneda. K. Chem. Conintun., 1999, 265. PhCHzOH
zeolitt: €ESM-S-supporttx Fe(JI1j nitrate
w PhCHO 99% micmwaves , 10 sec Ikravi. M.M,;Ajami, D.; Aghapoor, K.; Ghassemzadeh, M. Chem. Cornrnun., 1999, 833
silica-supported TEMPO, DCM
PhCH,OH
aq KBr , aq NaOCl, NaHC03 (pH9.1) Balm.; Fey, T. Chern. Cornrnun., 1999, 1795.
75%
PhCHO
Lr
KMn04/alunina , no solvent
* PhCIIO 30 z c €1a"iinour. A.R.; Mallakpour, S.E.; Imanzadeh, G. Cheni.Lett., 1999, 99.
94%
PhCH,OH
dCH q=o
S i O z ,CHzClz
-
ACID4
Kernag, C.A.; &hhitt.
0
89%
J.M. ; McGrath, D.V. Tetrahedron Lett., 1999,40, 1635.
CdI I~CH~CHIOH
1 % Os04 , 1.5% CuCl ,O2( 1 a h j s%I
P Y , MS 4 A , toluene, IOOT
c
C&13CH2CIIO
32% hetteryiekls with benzylic alcohols Coleman, K.; C o p p , M.; Thomas. C.; Tetruhedron LEtt.. 1999, 40, 3723.
Section 48
97
Aldehydes from Alcohols
PhCHzOH
CuC1-PhedPhH, 2
2
KZCO,
* PhCI-I0 86% ,IEflux , 2h Mark6 I.E.; Giles, P.R.; Tsukazaki, M.; ChellC-Regnaut, I.; Gautier, A.; Brown, S.M.; Urch, C.J. J. Org. Chain., 1999, 64,2433. 0 2
5% Pd()Ac), , Py , MS 3A
* PhCHO qumt toluene, 8 0 T , O2 Nishilnura, T.; Onoue, T.; Ohe, K.; Ilemura. S. J. Org. Chent., 1999, 64, 6750. PhCH, OH
c61113
<
4% RU(PPh3 )2C&/CKG
+
C J i ,,CHO
PhCF3 , 1 atm O2 ,6O"C, 15 h
OH
Takezawa, E.; Sakaguchi, S.;
52%
CKC= Kuriane coal GLC Org. Lett., 1999, 1, 713.
-
TMSOTMS ,C r q , neat
PhCHO microwaves, lOsec Heravl.;Ajami, D.; Tahar-Heydar, K. Synth. Conimun., 1999, 29, 163. PhCl1,OII
P hCI 1,OH Mirza-Aghayan, M.; P hCH, OH
C Q - H Y zeolite, 10 sec
-
PhCHO neat, microwaves Synth. Conzinun., 1999, 29, 785.
neutral A h 0 3 ,40% NHOH , H 2 0
MnS03*5II2O, KMn04 ,80°C Stavrescu, R.; Kimura, T.; Fujita, M.; Vinatoru, M.; Ando. X Synth. Coriimun., 1999, 29, 1719.
t
PhCHO
98%
98%
70%
quinolinium fluomchromate O -H
hexane, r t , 2 h
=
-
CHO
Rajkumar, G.A.; Arahindoo, B.; Murugesan, V. Synrh. Commun., 1999, 29, 2105.
DCM, 1 h Beravi. M.M.; Kiakoojori, R.; Mirza-Aghayan, M.; Tahar-Hydar, K.; Bolourtchian, M. Monur. Cheni., 1999, 130, 481.
57%
98
Coinpendium of Organic Synthetic Methods, Vol 11
Section 5 1
-
NH4+ C Q C T ,Monlmorillonite K10 PhMO PhCItOH J & u L M & L Kiakojoori, R.; Tahar-Hydar, K.Monut. Chem., 1999, 130,581.
92%
SECTION 49: ALDEHYDES FROM ALDEHYDES Conjugate reductions and Michael Akylations of conjugated aldehydes are listed in Section 74 (Akyls from Alkenes). (BnPPh3)2+ Cr2Q-’ , MeCN, reflux P hCH, CHO
t
PhCHO
qumt
Moharmnadpoor-Baltork, I.; Niknarn, K. Org. Prcp. Proceed. lnt. 1999, 31, 335. Related Methods:
SECTION 50:
Aldehydes from Ketones (Section 57) Ketones from Ketones (Section 177) Also via: Alkenyl aldehydes (Section 341)
ALDEHYDES FROM ALKYLS, METHYLENES AND ARYLS
Wan, Y.; Barnhurst, LA.; JQ~tateladze. A.G, Org. Lctt., 1999, 1, 937.
SECTION 51: ALDEHYDES FROM AMIDES
dNri - -A C d r ( I i ) C I , THF, rt , 15 min
Ph
Ph
96% White, J.M.; Tunoori. A.R.; Geore. G.I. J. AIII.Chern. Soc., 2000, 122, 11995.
Section 54
99
Aldehydes from Ethers
SECTION 52: ALDEHYDES FROM AMINES
PhCHzNIl,
2 . 2 q Ph(Cl)S=Nt-Bu , DCM
.
2 e~ DBU -78°C 3. 1M €16, DCM-ether . Matsuo, J . 4 ; Kawana, A,; Fukuda, Y.;
. .
Chem. Lett.. 200Z, 712.
TMSCl , Nid, 1% HzO
PhCIIN -NMe, ;,A-
. .
98~98%
Ph(JHo
*
PhCHO
95%
MeCN , 2 min Ramana, K.V.; Arifuddin, M. Chem. k t t . , 2000, 827. Ketones from Amines (Section 172)
Related Methods:
SECTION 53: ALDEHYDES FROM ESTERS NO ADDITIONAL EXAMPLES
SECTION 54:
ALDEHYDES FROM ETHERS, EPOXIDES AND THIOETHERS
@ OMe
Maeyaina, K.; Kohayashi, M.; -wa.
P hCl IZOTMS
NiCh , Zn ,p-xylene
reflux, 3 d 97%
N. Synfh. Cnmmrtn., 2001, 31, 869. BiCI3, BnPPh3 HSOs DCM , microwaves, 3 min
+c
PhCHO 90%
w Mallakpour, ; S.E.; Balork, I.M.; Adihi, H. Synth. Commun. 2001, 31, 1625. '
1
PhCH20S i M q
-
moIite HM-5 suppoited Fe(N03)3
m i m w a v e s , 20 sec Heravl.;Ajaini, D.; Ghussemzadeh, M.; Tabar-Hydar, K. Synth. Co,iimun., 2001, 31, 2097.
PhCHO
98%
Section 54
Compendium of Organic Synthetic Methods, Vol 11
100
zeolite HZSM-5 , Fe(NO& PhCHzOTHP ; -
I
.
S
.
.
+ PhCHO DCM ,reflux , 6 h Ajami, D. Mona. Chan., 200Z, 132, 871.
.
91%
K 2 F a 4 ,clay , M&N, 3 h * PhCH20Si M q PhCHO 95% Tajhakhsh, M.; Heravi, M.M.; Hahihzadeh, S.;Ghassemzadeh, M. J. Chem.Res. (S),2001, 39. 3 eq Me3Al, DCM ,-30°C
* C3H7
10 min
C3H7&SPh Sasaki, M.; Tanino, K.; Mivashita. M. J. Org. Chem., 2001, 66, 5388. Bi(OTt),*x
H20,
-
lcse
B i O C l 0 ~ - ~ 1 1CH,Ch_ ~0,
Phtj 0
25 min
*
92%
phFa'o 90%
Ph
Anderson, A.M.; Blazek, J.M.; Garg, P.; Payne, B.J.; Tetruherlron Ixtt., 2000, 41, 1527. 2.2 eq Li/TIIF , reflux /
cat biphenyl , 3 0 min Rama,
K.;
96%
DCM
20 min + ph>cHo Ph Ph Bhatia, K.A.; Eash, K.J.; Loenard, N.M.; Oswald, M.C.; ~YWULLL Trtruhedron Lett., 2001, 42, 8129. Ph
SPh
Tetruheclrrin k t t . , 2000, 41, 1073.
1 . 2 eq L i , TI1F t
Azzena. IT.;Demartis, S.; Pilo, L.; Pivas, E. Tetruhetlron, 2000, 56, 8375.
>95%
Section 54
Aldehydes from Ethers
101
1. VO(OEt)ClZ, EtOH , rt, 5h
Ph~ C H O 90% 2. aq NaCI , HCI Martinez, F.; del C a m p , C.; Wama. E.F, J. Chetn. Soc., Perkin Truns. I , 2000, 1749. Ph
DMSO, (ma),
CHzClZ, NEt3, -70°C 68% C5Hl1 C441 Rodriguez, A.; Nonien, M.; Spur. B.W.; Godfroid, J.J. Tetruhedron k t t . , 1999, 40, 5161. Fe(tpp)OTf ,dioxane retlux
c%1117
* CXH17-CHO
96%
Suda.;Baha, K.; Nakajima, S.-i.; Takanami, T. Tetruhedron Lett., 1999, 40, 7243. wet alumina supported GO3
90%
t PhCHO neat, 30 sex Ajami, D.; Ghassemzadeh, M. Synthesis, 1999, 393. Ileravl..; Ajami, D.; Ghassemzadeh, M. Synth. Conimun., 1999, 29, 781
Ph-OSiMe3
m;
PhCH20Si M q
C1O3 ,TMSOTMS , SiOz
-
PhCHO I X M ,25"C, 25 min b r a v i . M.M.; Ajami, D.; Tdbar-Heydar, K. Synth. Conitnun., 1999, 29, 1009. NaBrO3/A1CI3,MeCN Ph-OTHP
*
0.65 h , ixflux Mo hamm ad no or-B a 1tork. I.; Noumzi, A. R. Synthesis, I99 9, 487. I'h -o.rMS
PCWP-HzOz ,rt
PhCHO
w
95%
95%
Ph-CHO
CII,C12, 16 h
PCWI' = peroxohJngstophosphat Sakaguchi, S.; Yarnamoto, Y.; Sugiomoto, T.; Yamamoto, H.; J . Urg. Chcm., 1999, 64,5954. iXX,/NaBH,, THF
Pho-
-
PholI 0°C- rt Chary, K.P.; Mohan, G.H.; Jvenvar. r1.S. Cheni. Lctt., 1999, 1223.
95%
102
Section 55
Compendium of Organic Synthetic Methods, Vol 11
no
MeCN ,60"C, 5 h
-
No,
*Ot-h
O
Y OH J. Org. Chem., 2999, 64, 4676.
Eikawa, M.; Sakaguchi, S.;
FeN03-Montmorilkmite K10
P hCH20TMS
minuwaves Mojtahedi, M.M.; Saidi, M.R.; Bolourtchian, M Synth. Commun., 1999, 29, 3283.
.
A,, 0
, S d l
PI1
Ph J?J.ouzaha
<
72%
*
90%
W
up,,
=- Ph 82% THF,rt, 1h Etemadi, S.; Karimi, B.;Jarrahpour, A.A. Synth. Commun., 1999, 29, 4333.
u;
Ketones from Ethers and Epoxides (Section 174)
Related Methods:
SECTION 55:
ALDEHYDES FROM HALIDES AND SULFONATES 1. Bu3MgIi ,0°C , toluene-Ti4F
B
r
\ e /B
r
3. DMF 2. aq citric ,0°C acid ,30min 84%
Iida. T.; Wada, T.; Tomimoto, K.; Mase. T. Tetruhedron Lztf., 2002, 42, 4841.
DMSO, ZnO ,NaBr 140"C, 14 h L C Guo, 2.; Sawyer, R.; &&&JSynth. . Contnzun., 2002, 3 1 , 667. Guo, Z.; Sawyer, R.; Prakash, I. Synth. Coniriiun., 2001, 31, 3395.
ri"
DMSO, NaI-ICO3
rt,2h Ph pavichandran. S. Synth. Conzmun., 2001, 31, 2185.
H
O
58%
dcHo
Ph
70%
Aldehydes from Alkenes
Section 59
6
103
SECTION 56: ALDEHYDES FROM HYDRIDES
(CI-IzO), ,Mgaz-NEt3 THF,lSh
83%
Hofslfikksen, N.U.; Skattehol, L. Actu Client. Scund. 1999, 53, 258.
SECTION 57: ALDEHYDES FROM KETONES PCCI3 , DMF ,SO2 rnkmwaves , 2 inin Paul, S.; Gupta, M.;
Synlett, 2000, 1115
SECTION 58: ALDEHYDES FROM NITRILES NO ADDITIONAL EXAMPLES
SECTION 59: ALDEHYDES FROM ALKENES
Q-J3
2.5% Kh(acac)(COh, MeCN
50 psi €I,/CO , 65°C
*
LCkI =
1
92% (81:19 anh':syn) Krauss. 1.1.; Wang, C.C.-Y.; Leilrhton. J.L. J. Am. Chern. Snc., 2001, 123, 11514. P hCI-I=CH,
0.5% aq RuC&(II,O), , 1.5 eq Oxone
4.7 UJ NaHC03 , 1 1 2 0 Zhang, C. J. Org, Clzeni., 2001, 66, 4814.
*
PhCHO
73%
Compendium of Organic Synthetic Methods, Vol 11
104
5% v catalyst
*
5 eq P h S H, 1 d
Baucherel, X.; Uziel, J.; S
S
.
ocH 58%
*x
. Org. Chem. 2001, 66, 4504.
CO/€12,toluene, 180°C
A
Ph
Section 5 9
58% conversion [Rh(awc)(CO)z] SO%ee,S chiral carbohydrate phosphine Ph '1 -M.; Phmies, 0.;Net, G.; Ruiz, A.; Claver, C. Tetrahedron Asymm., 2001, 12, 651. . I
2
6
Ph
.,
Rh(xac)(CO)z , CO/H2
chiral furanoide phosphite68% (35% ee, 5') phosphor amidate Ruiz, A.; Claver, C . Tetruherlron Asynzm. 2001, 12, 2827.
*I *I
furanoside phosphine-phosphi te l$and Rh(aca~)(CO)~ ,CO/H,
4 \
Ph
55% (49% ee ,S)
Ph Pknies, 0.;Net, G.; Rulz.; Claver, C. Tefruhedron Asymm, 2001, 12, 3441.
CO/H2, c h i d diphosphine ' - hP
40"C, 46 h
Hegediis, C.; Madrisz, .I.; Guly6s, H.; SziillGsy, A,; Tetruhedron Asyinm. 2001, 12, 2867.
6
Ph
92% (47% pe, R)
ph
CO/H2, Pt catalyst, SnCl,
*
chiral diphosphite hgand , 23°C 20 h
A
ph
C 1-10
+
Ph-
(85 86% ee Bakos.;Cserepi-Szllcs, S.; G8m6ry, A.; Hegediis, C.; Markb, L.; Szollfisy, A. Cun. J . Client., 2001, 79,725.
\ -
cat Rh(acac)(CD), , NaPHOS
CO/HZ ( 1 0 bar) , 120°C
Klein, 11.; Hackstell, R.; Wiese, K.-D.;Borgmann, C.; Beller. M. Angew. Client. h i t . E d , 2001, 40, 3408.
CIIO 15) 71%
CHO
Section 60
Aldehydes from Misc.
105
KMn04.CuS04*SH,O E M ,rt, 3h Gijksu, S.; -,&,
* o r Y Y H o 6 5 %
Synth. Conzniun., 2000, 30, 1615. Rh(CO)*(dpm), CO/H2 , 120°C
M
CSHI 1
* C5H11 M
his-phosphine complex , 1 h
C
H
O
90%
van der Veen, L A . ; Kamer, P.C.J.; van Leeuven, P.W.N.M. Angew. Chem. Int. Ed., 1999,38, 336.
REVIEWS: ”Recent Advances on Cherno-, Regio- and Stereoselective Hydmformylation.” Breit. B.; Seiche, W. Synrhcsis, 2 0 0 1 , 1. Related Methods:
SECTION 60:
Ketones from Alkenes (Section 179)
ALDEHYDES FROM MISCELLANEOUS COMPOUNDS
-w
SnBu3
t-BuOH , 50°C
*+++
/
/
VO( OCHzCF,)C12/36 h 100% VO(OCII2CF3)C12/3 h 60% 19% IIlrao.;Morimoto, C.; Takada, T.; Sakurai, 11. Z’etruheilron Iztt., 2001, 42, 1961. CuCl/Kieselguhr, O2 P hCI I=N-OH
*
DCM , 20 mii Jlasherni. M .M.; Beni, Y.A. Synth. Conlniun., 2001, 31, 295.
PhCHO
quinolium dichmnatt:
* PhCHO MeCN , reflux, 30 min SddeLhl.;Moharnmadpoor-Baltork, 1.; Azurii, M.; Mazidi, M.R. Synth. C O / / l / l J l U l . , 2001, 31, 435. PhCH=N-OII
.
1
96%
97%
106
Compendium of Organic Synthetic Methods, Vol 11
CBr, , MeCN , reflux Ph~
O
A
C
*
5h
Section 60
mCH
Ph
81%
Ramalingam, T.; Srinivas, R.; Reddy, B.V.S.; Yadav, J.S. Synth. Commun., 2001, 31, 1091. P y W OQF,3% H202
P hCN=N-OH
* PhCHo acetone , -1O"C, 20 min Gmgglv. N.C, ; Sukai, A.K.; De, S.; De, P. Synth. Conitnun. 2001, 31, 1607. BnPPh3 HSO, ,BiC13
P hCH=N-OH
.
; -
I
.
*
83%
PhC€fO
94%
M d N ,reflux, SO inin Baltork, I.M.; Adihi, H. Synth. Conimun., 2001, 31, 3401.
DDQ , DCM, 1120,2 h
* PhCI-IO Chdndldbekhdr.; * ... . Reddy, Ch.R.; Reddy, M.V. Chenz. k t t . , 2000, 430. PhCH=N-NHTs
-31.
-
[Ni(en)3]&03 ,CIlCl,, 5 min P hCIkN-NMe 2 A,; Arifuddin, M.; Rao, M.V. Synlert, 2000, 14x2.
85%
PhCHO
92%
quinoliuxn fluomchromate MeCN
MeO MeO OMe Bose. D.S.; Narasaiah, A.V. Synth. Cornnzun., 2000, 30, 1153. p2Me
OMe
( B u , N ) ~ S ~ ODCE ~, N-NHCONI-I, 91%
Chen. F.-E.; Liu, 1.-P.; Fu, €4.; Peng, Z.-Z.; Shao, L.-Y. Synth. Commun., 2000, 30, 2295.
P hCH=N- -OH
0
5"C, 20 lnill Chaudhari, S.S.; &am anchi. K.G. Synthesis, I Y Y 9 , 760.
*
PhCHO
94%
Section 6OA
Protection of Aldehydes
N-OH
107
peroxymonosulfateSi02 microwaves, 15 inin
MLS
85% Bose. D.S.; Nusaiah, A.V.; Lakshminarayana, V. Synth. Commun., 2000, 30, 3121.
Cu(N03)2*Si02 , 5 inin
P hCI I=N-OH
micmwaves . . GhlrlC1.; Asghari, J. Synth. Conmiun., 2000, 30, 3865. a
C
H
c1
=
N -OH
PhCHO
b
DCM ,rt ,40min
*
AcO OAc
C1
nC 95%
c1
c1
80%
Bose.; Narsaiah, A.V.
0
Synth.Conrriutn., 1999, 2Y, 937.
a C H = N - O € I (BU4NhSz08, %2 DCE 9 0 H c J*- J reflux, 1 h
MLS OMe MLO OMe Chen.; Liu, A.; Yan, Q.; Liu, M.; Zhang, D.; Dhao, L. Synth. Commun., 1999, 29, 1049.
PhCH( -c>or-Bw
BiCl, , CHC13 * PhCHO reflux, 10 min ; Aliyan, H. Syntlz. Conintun., 1999, 2Y, 2731.
90%
I2 , MLCN ,reflux PhCI I=N-OH Ir PhCIIO v. J.S, Sasmal, P.K.; Chand, P.K. Synth. Commun.,1999, 2Y, 3667.
96%
SECTION 6OA: PROTECTION OF ALDEHYDES K2Fe04 , Montmorillonite K10 Ir
E M , reflux , 10 inin ; Ilahihzadeh, S.; Ghassemzadeh, M.
bravi. . , .. . s Monat. Chom., 2001, 1.32, 985.
PKHO
95%
Compendium of Organic Synthetic Methods, Vol 11
108
Section 60A
N-Me-piperidiniun Q03Cp, AlZO,
* PhCHO dioxane ,reflux , 3 0 min .M.; Mohanazadeh, F.; Sarahi, S.; Ghassemzadeh, M. Monot. Chcm., 2001, 132, 1229. PhCH=NOH
IIS(CH2hSH. CdIz, 75 S
~ C
PhCHO
.-cI>
*
microwaves
85%
Sandhu, J.S. J. Chein. Res. (S), 2001, 313.
Laskar, D.D.; ;-
O.l%Bi(OTf),=x H z O , MeCN
PhCHO
3qAriO
Carrigan, M.D.; Eash, K.J.; Oswald, M.C.;
‘
4
0
A OAcc
91%
Tetruhedron Lett., 200Z, 42, 8133.
HSCIIzCHzSII,Iz, A 1 2 0 3
P hC1I 0 Deka, N.;
92%
I
10 min Cheni. L.ett.. 2001, 794. cat N z 0 5 , H 2 0 2 ,NH.,I3r, 5 h
* CllH23CH0 DCM/HzO, 1.75 h Mondal, E.; Bose, G.; Sahu, P.R.; Cheni. Lett., 2 U U 1 , 1158. C11 H,,CH(SEt)2
80%
HSCH-CIIzOH, 2101nin , DCE P hCI I 0 a t r ~ ( d P P ~ ) ( P - O H )(BF,), l,
* ]:(--hp
90%
MgSO,, HzO Battaglia, L.; Pinna, F.; Strukul, G. Ccm. J. Chcrn., 2001, 7Y, 621. 3 eq CIC12,4 q LiI, aq EtOAc Ph
75°C. 12 h
T .,dl . ck.;Baima, D.K.; Baati, P.; P hCIIO
92% Mioskowski, C. Angew. Chmt. Int. Ed., 2001, 40, 1281.
HS(CII,),SH , cat LiOTf, 0.1 h solvent f ~ e
*
Ph ‘SJ
rllDUZdhrldl.; .. . , Eslami, S . ; Karimi, B. Bull. Chein. Soc. Jpn., 2001, 74, 2401.
99%
109
Protection of Aldehydes
Section 60A
H S C H ~ C I - ~ ~ C H Z0.1 S HI,2 rt , 10min
P h q o OMe m
f.'irouzahadi. K; Jrannoor. N.; Hnzarkhani, €1. J. Org. Cli~nz.,2001, 66, 7527.
1.2ethanedithbl k1C13, MeOH 15 iiiin 92% Muthusamy. S.; Bahu, S.A.; Gunanathan, C. Tetruherlron Lxtt., 2001, 42, 359.
PhCIIO
HSCIIzCH2SH. LiBF, MtCN ,rt, 1 h
Yadav. J.S.; Reddy, B.V.S.; Pandey, S.K. Synlett, 2001, 238.
cetylMe3N-Br3 , 5 rnin.r CHz(32
M
e
O
0-
C
H
HOC€12CH2011,ZrPS03H ~
~
90%
~
CIIZC1,, reflux , 1 h
. . Cunnl.; Epifano. F Marcotullio, M.C.; Rosati, 0. Synlett,, 2 0 0 1 , 1182. Ph+OMe 0 Me Ono, F.; Negoro, R.;
PhSH ,2076 LiBr toluenc , 25°C
*
Ph+OMe
90% SPh
Synlett, 2001, 1581.
claI] K@)W12040*31120
acetone, reflux , 1 h *
97%
U . ',' Tangestaninejad, .M S.; Mohamnmadpoor-Baltork, .H. I.; Mirkhani, ; V.; Yadollahi, B. Tetruherldon Lrtt., 2001. 42, 6771.
O
93%
Mondal, E.; Bose, G.; Khan. A.T. Synlett, 2001, 785.
CI-I0
O
\ /
Coinpendium of Organic Synthetic Methods, Vol 11
110
Section 6QA
€ISCH2CH2CH2SH,0.75 h ,r t
c1
Ph4O"^ OMe
YAYu"CIICl., 0
v; . * I-Iazarkhani, H. Synlerr, 2001, 1641. '1.
AczO , 10%LiBF, ,40"C
Ph C I O
PhCH(OAc),
t
20 h Sumida, N.; Nishioka, K.; Sato. T. Synlett, 2001, 1921.
95%
Samajdar, S.; Basu, M.K.; Becker, F.F.; Banik. B .K. Tetrahedron Lett., 2001, 42, 4425.
PhCHO
O.l%Bi(OTf)3*xH 2 0 , MeCN
* Ph
41
~i+~-inontmorinonite toluene ,ethylene glycol, 1 h
Kawahata, T.; Mizugaki, T.; Ehitani, K.;
PhCHO
IIO@-JSH
Amherlyst- 15, DCM , 1 h
>99%
Tetruhedron Lett., 2001, 42, 8329.
*
Ph4:] 84%
. . Balllnl.; Bosica, G.; J&ggLL Mazzacani, A,; Righi, P.; Sartori, G. Synthesis, 2001, 1826.
ph
HSCIIzCIIzSII, DCM , 2 m i n PhCIIO
POCl3-montiiwriIlonite ,rt
*
96%
Jin. T.-S.;Sun, X.; Ma, Y.-R.;Li, T.-S. Synth. Conitnun., 2001, 31, 1669. PhCII=N-OH
,.
Zn(N03),6 H 2 0 , acetone, S O ,
*
niicmwaves , 4 inin J amaiii i. B.; Kiasat, A X . Synth. Coniinun., 2000, 30, 4129.
PhClIO
90%
Section 60A
C311F H O
Protection of Aldehydes
111
AcZO, PVC-FeCl3
t C3H7CH(OAc), 85% rt , 15 miri Z d f g ~ IM.A.; . Kiany-Borazjani, M.; Sadeghi, M.M.; Mohammadpoor-Baltork, I.; Memarian, H.R. Synth. Coinm., 2000, 30, 2919.
Phcrro
IIS(CI12hSI-I , O S M LiC104, ether
* Ph
\
2h
S
Tietze. J,.F,; Weigand, B.; Wulff, C. Synthesis, 2000, 69. FeC13.6 HzO , it , 15 min
Fh’
*
176%
PhCHo
96%
al. A;; Laxman, E.; Reddy, P.S.M.M. Synleri, 2000, 1476. OMe OMe
IISCH2CII2CII2SH , silica chloride P
DCM, r t , 10min
h
4
1
3
94%
v . . ; Kaiiini, B.; Hazarkhani, €1. Synlen, 2000, 263. PhCHO
2.5% Ctl(OTf), , A c ~ O, rt
* P h 4 O A c DCM,2h OAc Chandra, K.L.; Saravanan, P.; V.Ii, Synlett, 2000, 359.
96%
w.
P hCHO
A c ~ 10% , NBS ,rt , 6 h
*
. . Kanml.; Seradj, If.; Ehrahirnian, G.R. Synlett, 2000, 623. PhCI-I0
PhCI I( OAc),
95%
ethylene glycol, microwaves
NaS04-Si02,4 inin U l a v . .I.&; Reddy, B.V.S.; Srinivas, R.; Ramaiingam, T. Synleft, 2000, 701.
Qandear. B.P.; Makone, S.S. Org. Prep. Proceed. Int., 2000, 32, 391.
95%
112
Compendium of Organic Synthetic Methods, Vol 11
PhCI-IO
-
HOCI1zCHzS€1, 4% z1C1,
Section 60A
Ph< ]:
91%
DCM, r t , 30min
Seradj, H. Synlctt, 2000, 805.
NBS , aq acetone
*
PhCIIO
93%
Tahaei, M.H. Synlett, 2000, 1798.
-G;.
.
BiC13 , MeOII, 30 min PhCI-I(0Me)z * PhCHO . Bahu, R.S.; Reddy, E.V.; Yadav, .IS. Chein. Lett., 2000, 1074.
92%
wNpoH
BdndLdT.; , ,. Makone, S.S.; Kulkarn,
S.R. Monut. Chem., 2000, 131, 417.
clay-(TMS)zchromate DCM , 4 0 inin
+
e
C
H
I-IS(C€I&SH t O.lInBr3,UCM,lh
Ceschi, M.A.; Felix, L.de A.; pim20nrp
0
90%
Heravi. M . M ; Ajuni, D.; Tajhakhsh, M.; Ghassemzadeh, M. Mnnut. Chetii., 2000, 131, 1109.
P hCI I 0
87%
ph4f7 80%
-
Tetruheclron Lett., 2000, 41, 9695.
Montmorillonite K-10 , Fe(NO&,
microwaves, 60 sec ; Ajarni, D.; Majtahedi, M,M.; Ghassemzadeh, M. Tetruhcdron Lxtt., 199Y, 40, 561. 2.5 "q CAN , 5 rnin ,70"C
+
Ph
PhCHO
MrCN , 1 1 2 0 Ph Ates, A.; Gautier, A.; Leroy, B.; Plancher, J.M.; Quesnel, Y.; Markli, I.E. Tetruheclron La.,1999, 40, 1799.
90%
CIIO 70%
Section 6OA
Protection of Aldehydes
HSCH2CH2CI12SH , LiOTf PhCHO solvent f i v e , llO"C, 5 min
113
* Ph---(l3
quat
Firouzahadi. H.; Karimi, B.; Eslami, S . Terruhedr-on Lett., 1999, 40, 4055. MagrieveTM,CHC13
PhCII(0Meh
it,
go. K.-Y,; Park, S.-T. Tctr-uhedmn Lttt., 1999, 40, 6025.
95%
PhCHO
t
10min
f o r m acid with several substrates
HS(CII&SII. LiBr , 80°C
PhCHO
cz'
1.5 min (neat)
Lrouzahadi. IJ.: Irannoor. N.; Karimi, B. Synrhesis, ZY99, 58. 5 % KtW13(I'Ph3h, 23 h
5% 2,4,6conidine, 1.2 D M s g UIZh 4 y ethylene glycol u h u r n . J.&; Perry, M.C. Org. LL'tt., 1999, 1, 769.
85%
3 eq propylene glycol , 1% NBS
PhCI-IO
95%
P h q ] (Et0)3CH , 2 eq MeOH , DCM rt,6h . . &muu&&.; Ehrahimian, G.K.; Seradj, M. 01%. Lett., 1999, I, 1737. +
- --<")
5% ZCI,, DCM, rt OMe
IiSCH,CH,SH
Firouzahadi. H.: Iranpoor.
P hCI I 0 u-zcJl>.r > 4
' 7 .
cdi ,1-
. .
cr 10
N.;K a r h i , B. Synlett, 1999, 319. (EtO),CH ,ZiClq, neat
~
N,; Karimi, B. Synlert, 1999, 321. rIscIi,cIr,sH,
Anand, K.V.; Saravanan, P.;
neat , 2
11
97%
+OEt
It
qumt
S
OEt
cu(o~~--sio,
m.V.K, Sywlett, Z9Y9, 415.
c & 1 3 4 ; 3
93%
Section 60A
Compendium of Organic Synthetic Methods, Vol 1 1
114
PhCHO
1 . 3 eq (EtOhCH, E O H , rt DCM,NBS 2.10% aq NaOH
95%
OEt
. . Kanml.; Seradj, H.; Ehrahimian, G.-R. Synletr, 1999, 1456. (EtO),CH ,cat DDQ, rt t
P hCHO
95%
EtOH , 10 h
. .
OEt
anmi. B.; Ashtiani, A.M. Chenr. k'tt., 1999, 1199.
PhCHO
ethylene glycol ,CdIz , 1.5 min mi an w ave s
=-
ph--(I]
90%
Laskar, D.D.; Pra.iapati. D, ; Sandhu, J.S. Cheni. Len., 1999, 1283.
P hCHO
IISCH2CIi2CHlSH ,HCI, AcCl , MeOH , 2 min
. .
Synth. Coriirnun., 1999, 29, 697.
Clayan , microwaves P h 4 s ESE tt
110 yec
89%
PhCHO
t
Meshrain. H .M.; Reddy, G.S.; Sumitra, G.; Yadav, J.S.Synth. Commun., Z999, 29, 1113. (Et0)sCH , cat WCl6
* PhCH( OEt), neat, rt , 10 min Firouzahadi H . Irarlnoor. N.; Kariini, B. Synth. Commun., 1999, 29, 2255. P hCHO
Ph
NO2
A1-NiCl2-CH20 ,TIIF
Bezhiirun, M.S.; Bez, G.; Barua. N.C. Chcwi. Lett., 1999, 325.
t
98%
Ph-CHO
77%
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 5 PREPARATION OF ALKYLS, METHYLENES AND ARYLS This chapter lists the conversion of functional groups into methyl, ethyl, propyl, etc. as well as inethylene (CHl), phenyl, etc.
ALKYLS, METHYLENES AND ARYLS FROM ALKYNES
SECTION 61:
-
10% Ni(cod)z, 40% PPh3
toluene, it ,0.25 h
&do. S.; Kawasaki, T.; Tsuboya, N.; Yainamoto. Y. J. Org. Chcni., 2001, 66, 796.
Ph
=
Pd(PPh3)4, T H F , 100°C , 12 h Bu
= =
m;
Bu
* P
. I . Radhaluishnan, IJ.; Yakeda, A,; Rubin, J. Org. Chent., 2001, 66, 2885. 1
h
-
Q
X
B
M.;Rubin, M.;
’ U
Ph
“Ph I-hang, Q.; Hunter, J.A.; h o c k .
Bs. . Org. Lrtt., 2001, 3, 2973.
68%
I I
116
Section 61
Cornpeiidiuin of Organic Synthetic Methods, Vol 11
Phi-PPh
? Org. Lett., 2001. 3, 30x3.
1.
Bu
*
5% Pd(OAc)z, 10 h 5% PPh3, NBu3 100°C
'tBr Zhang, H.;
,DMF
=
=S -O2Tol (C3&)Ti(Oi-Prh, -50°C
Bu 2. -S02T0l 3 . H+
Bu
I&
54%
9 f"
SOzTOl
65%
Suzuki, D.; Ilrahe, H.; Sato. F. J . Anz. Cheriz. Soc., 2001, 123, 7925. B
u
e
, PhII,rt
~ r ( c ~ d ) C l ] ~ d p 201nin pe, 84%
Takeuchl.; Tanaka, S.;Nakaya, Y . Tetrulzedron Lett., 2001, 42, 2991. 5% KhCI(PPh,), , 10%AgBFq CHCS ,50"C, 2 h
83 %
Oh.;Sung, H.K.; Jung, S.H.; Lim, Y.M. Tetruhedron Lett., 2001, 42, 5493.
10% [Rh(C0)2Cl],
toluene, 110°C
J.W. Tetruhidron Lxtt., 2001. 42, 5x09.
51%
Section 61
Alkyls from Alkynes
-
117
q~'oqcoz~
C<)LMe
/
cat N i ( ~ a c ) ~ - P P h ~ EtzZn, PhOH ,THF rt
/
/
COzMe
COzMe 5)
(95
78%
Mori, N.; Ikeda. S.-i.; Odashima, K. Chent. Conimrm., 2001, 181. EtO,C-CN, 2% Ru complex, DCE 30 ,6O min C
Me02
M t
Me02C
a
2
a
MLQC
Yamamoto, Y.; Okuda, S.;Itoh. K. Chern. C0!??1?2l4n., 2001, 1102.
COzEt
83%
hv ,p-TolCN
1) 42% Moretto, A.F.; Zhang, 13.-C.; Marvanoff. B.E. J. Am. Chern. Snc., 2001, 123, 31.57. COzMt:
B~
5% Ni(dppe)Brz ,Zn MtCN , 8 0 T, 8 h CO2Me
Mt:OZC COzMt:
Shanmugusundaram, M.;
80%
Section 61
Compendium of Organic Synthetic Methods, Vol 11
118
1 . C02(COb , hexanes 2. NMO , E M , -35°C
Me-
* M y J
ID
/
98%
Marchueta, I.; Olivella, S.; SolB, L.; Moyano, A.; Org. Lett., 2001, 3, 3197.
..
Daurn G.; hd~. R.C Orb. LEft., 2001, 3, 4035.
F
.
a;Zhang. Y.;Wang, H.; Wang, K. Tetrulieilron Lett., 2000, 41, 8687.
pH
-
Ph
-
1. PhMgCl, CbHlz , 8 0 T
-
*nHph
2. DMF , 0°C rt 3. TsOH , PhI4 Forgione, P.; Wilson, P.D.; hllis. A.G. Tetmheilrnn Lett., 2000, 41, 17.
Ph
=
decahorane, P d C
-
Ph M t O H , rt Lee, S.H.; Park, Y.T.; Yoon. C.M. Tetruhedron Lett., 2000, 41, 887.
=$
Ph
Bu
=
Z
Bu
5% Pd(PPh?)A, THF, 6S"C, 8 h
*
Bu
=
92%
0
qon
56% Gevorwan. V.; Quan, L.G.; Yamamoto. Y. J. Org. Chem., 2000, 65, 568.
ph
Bu
97%
Section 61
Alkyls froin Alkynes
=
Et
1 . CpzZrEt, 2. MtCN
Et
3. NiCh(PPh3)z
C, H7-
C3H7
119
Etlhc
* Me
C3H7
66%
Takahashi. T.; Tsai, F.Y.; Kotora, M. J. Ant. Chent. Soc., 2000, 122, 4994. BuCrCH, E X , rt, 15 min Meo2 1% Cp*Ru(cod)CI
Bu Yamamoto, Y . ; Ogawa, R.; J&&-&
Cltent.Con~ntun.,2000, 549.
1. BuGCH ,1'IIF ,6O"C 2. SiOz
==L
(1
(Oc),Cr
-
Bu
89%
").o
HO
88%
C02Et C02Et narluenea. 1.;Lbpez, L.A.; Martinez, S.; Tomis, M. Teirulzedrnn, 2000, 56, 4967. w 1 3 -
, MoC1.j , Al
DME ,50°C, 1 h
Hara.;Guo, Q.;
'
Clwnz. Lett., 2000, 140.
C02Me F L
C C
O
z
M
e
O
z
M
c
2.5%Pdz(dbah, DMAD PPh3, 0.5 M ,toluene, lh
Yamamoto, Y.;Nagata, A.; I t o h . T e t r u h e d r o n Lett., 1999, 40, 5035.
I
k02Me
61%
120
S&U I J;.I
Section 63
Compendium of Organic Synthetic Methods, Vol 11
Vu, A.T.; McCullagh, J.V.; Kinoshita, A. J. Am. CIiein. Soc., 1999, 121, 3230.
PhCECH , heat
(OC),Cr Ph
88% OH pullev. S.K.; Sen, S . ; Vorogushin, A.; Swanson, E. 01-g. Lett., 1999, I, 1721.
SECTION 62:
ALKYLS, METHYLENES AND ARYLS FROM ACID DERIVATIVES
hv , IIgF2 , Ar , MtCN
I'h
CO 2H
.. IIahlhl.; Farhadi,
SECTION 63:
Ph
83%
S . Tetr-dierlI-onLtii., 1999, 40, 2821.
ALKYLS, METHYLENES AND ARYLS FROM ALCOHOLS AND THIOLS 4 q EtMgBr , Ti(0i-Pr), ether , it
O.L.; Isakov, V.E.; Khniel'nitskaya, E.A. Synlett, 2001, 49.
&
Section 64
/
Alkyls from Aldehydes
a PhBr t Pd(OAc)z/PPh3,6 ,Cs2C03 ,o-yxlene h
*
121
& 94%
/
/
/
Terao, Y.; Wakui. €1.; Satoh, T.; Jvliura. M.; Nomura, M. J. Am. C h m . Sor., 2001, 123, 10407.
SECTION 64:
ALKYLS, METHYLENES AND ARYLS FROM ALDEHYDES
DCM , r t , 20 h . V.; Ruhin, M.; I-iu, J.-X.; -to.
Y. J. Org. Chem., 2001, 66, 1672.
b
O
X
0
Llst.;Castello, C. Synletr,
acetone , C€ICg , rt cat Lpmline
2001, 1687.
Ohishi, T.; Kojirna, T.; Matsuoka, T.; Shiro, M.; Kotsuki. II. Tetrulzedron Lett., 2001, 42, 2493.
78%
Compendium of Organic Synthetic Methods, Vol 11
122
Section 65
Related Methods: Alkyls, Methylenes and Aryls from Ketones (Section 72)
SECTION 65:
ALKYLS, METHYLENES AND ARYLS FROM ALKYLS, METHYLENES AND ARYLS 1. BuLi ,TMEDA ,ether 2. C8HI7Br,ether
C8H17
94%
Yong, K.11.; Lotoski, J.A.; Chong, J.M. J. Org.Cliern., 2001, 66, 8248.
PhI , hv
41% conversion (85% yield)
Ho.;Ku, C.-K.; Liu, R.S.H. Tetrulzetlron Lr.tr., 2001, 42, 715.
5% PdCb(PPh3)2, 10% PPh3
N-'
i-eflux , 12 h
70%
Mathieu, J.; Gros, P.; Fort. Y. Tetruhedron Letr., 2001, 42, 1879. Me2ClSi€I,hexane , 2 0 % AlCI,
* C,H,3 -SiMpC,
rt,2h
92%
w; Yamakawa, T.; Yainamoto, H. Tetruliecfrnn k r r . , 2001, 42, 5057. 7.
*
1. ClCOZPh, AgOTf it, MeCN , 3 0 min
SLMe3
. .
*
Y
Nakayasu, T.; I-Iatano, B.; Nagura, T.; Kozima, S.; Fujita, K . 4 Tetruherlron, 2001, 57, 109.
;-
Section 65
123
Alkyls fium Alkyls
C A N ,MeOH
2
*
rt , 15min
a
94%
CO ,Me
.hang, P.; Lu-LSynth. Conmitn., 2001, 31, 131.
''
2% chiral oxavmadium complex 2% TMSCl , 0 2 ,CHC13
*
OH
rt,ld
moH I
\
\
82% (51%ee) Chu, C.-Y.; Huang, D.-R.; Wang, S.-K.; UJL. 13.-5, Chprn. Commun., 200Z, 980.
Ph-H
Pd(0Ac)z. TiO(acac)z, 0 ,
* Ph-Ph
AcOH , 13O"C, autoclave, 4 h
+
Ph-011
(0.76 Okamoto, M.; Yamaji. T. Chent. Lptt., 2001, 212.
0.11
+
Ph-OAC 0.13)
76%
e- , cat NiBr2dmhp Zn anode, DMF
Bu,N BF, Cassol, T.M.;D m ; Navmo, M.; de. Neves, E.A. Tetruliedron Lc)tt., 2000, 41, 8203.
Sinha, S.; Mandal, B.;
CCH( SEt(E t)C02Et
CH(SEt)COzEt
5% Yb(0Tfh
2.5: 1 p:o 92% Tctr-uhodronLett., 2000, 41, 9109.
124
Section 65
Compendium of Organic Synthetic Methods, Vol 11
T i c & ,E M , 8 h
Ph-NEtz
O"C+
c
E
t
2 N
~
N
E
\ /
It
92%
Periasamv. . M.; Jayakumar, K.N.; Bharathi, P. J. Org. Chem., 2000, 65, 3548.
XSiMq
&SiMe,
CXH17
e-
t
*L C8H17
80%
Suga, S.; Suzuki, S.; Yamamoto, A.; Yoshida, J.4. J. Am. Chcm. SOC.,2000, 122, 10244. 01I
0-
-
LiC104, MeN02
3
Et Kim, S.; Kitano, Y.; Tada, M.;
71%
Tetralierlron Lett., 2000, 41, 7079.
I
i-Pr
Me
Me
3 eq hrucine , toluene rt,3h
i- pk Me
i-Pr
'Me 92% (40%ee)
Sato, S.;Kano, T.; Muto, H.; Nakadai, M.; J. Am. Clieni. Soc.. 1999, 121, 8943.
Tanka.; Sadeghipour, M. Angew. Cheiii. Int. Ed., 1999, 38, 159.
OMe
F
PhI, 3 eq TBAF,5 0 T ,22 h t
2.5%(allylPdC1)z 10%P(o-Tolh
Denmark.;Wu, Z. Org. L c x 1999, 1, 149.5.
2
P
h
e
\
O
M
e
88% + 12% Ph-Ph
Alkyls from Esters
Section 68
125
REVIEWS: “cine-and tele-Suhstitution Reactions,“
; Swiei-czek, K. Tetruhedron , 2001, 57,
1639.
SECTION 66:
ALKYLS, METHYLENES AND ARYLS FROM AMIDES NO ADDITIONAL EXAMPLES
SECTION 67:
ALKYLS, METHYLENES AND ARYLS FROM AMINES
PhH, Mn(OAc), , reflux IC Ph-NIINH2*HC1 Ph-F’h 75% Delnlr.;Reis, 0.;Ozgiil-Karaaslan, E. J. Chein. Soc., Perkin Trans. I, 2001, 3042.
SECTION 68:
ALKYLS, METHYLENES AND ARYIS FROM ESTERS ASYMMETRIC CONVERSIONS
96% (92%ee)
Mino.; Shiotsuki, M.; Yunamoto, N.; Suenag, T.; Sakamoto, M.; Fujita, T.; Yumashita.
KJ.Org. Client., 2001, 66, 1795.
of OCOZMe
; .Y-
.
. .
3
CHZ(C02h , 3 eq BSA LiO Ac , J XE
0, --
2% I’d(dha)2,40/0 R-9-PBN
*
95%(51%ee)
Sakaguchi, K.-e.; Iiatano, K.; Hai-a, 0. Tetruhedron LEtt., 2001, 42, 1297.
126
Compendium of Organic Synthetic Methods, VoI 11
Section 68
EtMgBr ,CHzCIz
1% CUCN ,-78°C 1% Pligand, 1 h
87% (73% ee) Alexakis, A.; Malan, C.; Lea, L.; Benhaim, C.; Foumioux, X. Synlett, 2001, 927.
0
OCOZPh
&Q&;
1% (C3€Id)PdCl/2,B S A 2.1%~ chird phosphine ligand
Kashiwagi, R.; Hoyashi, S.; Uchida, T.;
OAc
-0
CH(COzMe)z
CHz(C02Me)z , CI-IIC12, rt ’
98% (75% ee) Synlett, 2001, 284. CH(CO,Me>2
CH,(COzMe)2 , LiOAc , BSA , TIIF
I
I
85% (64% ee)
Mlno.;khta, S.; Ohtaka, K.; Sakamoto, M.; Fujita, T. Tetruhedron Lctr., 2001, 42, 4837. [pd(?13-qfI,)(=I]2 , EtzZn 2.5%~ 5% his-phosphine ligand , LiOAc
Ph 2
Ph
CH(COzMe>2
-
CHZ(CO2Me)Z , -20”C, 15 h * Ph&ph
Naik, S.;Gopinath, R.;
. Tetruherlron Ldt., 20(11, 42, 7679.
ph-YPh
97% (88%~ ee)
1. [Pd(n-allyl)Cl]z c h i d fenucenyl ligand
OAc
KugJ.;
2. BSA , cat KOAc, DCM CHz(CO,Me)z, 20°C
Lee, J.H.; Choi, J.S. Tetmlzedron
A.Tyiniii.,
CH(COzMe)r
2001, 12, 33.
>98% (96% ee ,S)
PhTPh Ph-Yph CH2(COZMe)Z , BSA ,4“C
OAc
*
cat [Pd(~l~-GHs)C1]2 , BSA chird amide-phosphine ligand
CH(C02Me)r
95% (85% ee) Mino. T.; Kashihara, K.; Yanashita, M. Tetruk~~dron Asyrrtnt., 200Z, 12, 287.
Alkyls from Esters
Section 68
127
CHz(C02Meb ,BSA , DCM chiral pyrmlidine his-sulfide
OAc
I
CH( q M e 12
I
b
Ph
7 d , r t ,KOAc
Ph
PhP -h
quant (81% ee) Jansat, S.; ; Muller, G.; DiCguez, M.; Aghmiz, A.; Claver, C.; Masdeu-Bult6, A.M.; Flores-Santos, L.; Martin, E.; Maestro, M.A.; Mahia, .I. Tetruhedron Asymm., 2001, 12, 1469.
d
Ph
&o.
CH( C02Meh
CH,(COzMe)2 , BSA , LiOAc
cat [Pd(q3-C3H7)C1]2 ,b h e n e phA P h chiral amino-phosphine ligand 94% (94% ee) -2O"C, 7 d T,; Tanaka, Y.; Sakamoto, M.; Fujita, T. Tetruhrdron Asymm., 2001, 12, 2435. Ph
1% [Pd(allyl)C1]2 , 3 BSA , 2 h 2.5% imino-phosphine ligand
OAc
I
ph
Ph
C H( q M e 12
feimcenyl-allyl arnine , ether 3 eq CH2(C02Me)2, LiOAc
I
ph
Ph
98% (97% ee ,S) Fukuda, T.; Takehara, A.; Jwao. M. Tetruhedron Asynirn., 2001, 12, 2793.
2.5% chiral thiazoline ligand 2.5% [Pd(q3-GH7)ClI2 , It
OAc
I I
2 XI B S A , CII2(CO,Me)z Ahrunhosa, I.; Gulea, M.; Levillain, J.; u s o n .
b
Ph
Ph 90% (87% ee) Terruhcrfronftsyinm., 2001, 12, 2851.
[ ( v ~ - C ~ I ~ ) P CH2(C02Me)2 ~C~IZ~ chiral pyriulidinopyridiie ligand
PhJ
p
h
B S A , KOAc
J 7 l 2
Ph
Stranne, R.; Moherc. C Eur. J . Org. Clietii., 2001, 2191. OAc
I
quant (84% ee, R)
CII2(C02Me), , KOAC ,BSA 1% Pd[$-C3115)CIz, DCM
DiCguez, M.; Jansnt, S.; Clietrt. Cninmrrm., 2001, 1132.
.; Ruiz, A.; Muller, G.; Claver, C.
quant (95% ee)
Section 68
Compendium of Organic Synthetic Methods, Vol 11
128
2 q CH2(C02Me)2,0°C , 2 d 2 q B S A , 2 eq KOAc
I OAc I
&Ph
CE-I(O,Me), I I
L
Ph
cat P ~ v ~ - G H ~ ) c ~ I , 8% light fluomus phosphnie ligand
Phd
chird phosphine-hydrawne ,BSA LiOAc , DCM ,it, 20 h
p h4
P
h
95% (99% ee) Cavazzini, M.; Pozzl.~.; Quici, S.: Maillard, D.; a u . D, Chent. Commun., 2001, 1220.
ph
Ph
Mmo.; Ogawa, T.; Yarnashita, M. Heterocycles, 2001, 55, 453.
P
h
86% (92% ee)
CH2(C02Me)2 , KOAC N,O-his-TMS-acehmile
chiral P,N-ligand
93% (37% e e , S) ,&m. C G , ; I h i n n i i , D.; Faraone, F. Tetruhedron Asymm., 2000, 11, 4753.
.*
A
PhB(OH), , Ni(acach, T I l F Dihd-11, KOH, reflux ferrocenyl-pho.sphine ligand
-2
55% (18% ee) Chung, K.-G.; Miyake, Y.; Yemura, S. J. Clzem. SOC., Perkin Truns. 1, 2000, 15.
/nl\
Ph
Ph
phosphino-hydroxyhinaphthyllgand
&Ph
Ph
89% (99% ee) Kodama, II.; Taiji, T.; Ohta. T.; Purukawa, I. Tetruhedron Asymnt., 2000, 11, 4009. CH2(C02Meh , toluene, LiOAc 1% Pd(dha)2, c h i d amino-phosphme Ph
Ph
Ph
x;
Gong, L.; Chen, G.; Mi. A.: Jiane. Pu, F.; Cui, X.; Char, A.S.C. Terruhdron Asynrrri., 2000, 11, 4297.
95% (58% ee)
Section 68
Alkyls from Esters
129
CH(CDzMeX I
II
L
Ph
Ph
- Phd
chird phosphine ligand
P
h
79% (74% ee) Mino. T.; Tanaka, Y.; Sakamoto, M.; Fujita, T. Heterocyckm, 2000, 53, 1485.
r^(
O C O ~ M ~ CH.r(COzMeh .4o"c Pdcatdyst , 12 h
=e CH(C O,Me)z
68% (92%e e S )
m i n i . Y,; Shibatomi, K. J. Ant. Chein. Soc., 2001, 123, 2919.
CII(CD2Meh
*A/
NLICH(CO~M~)~ Ph-o(702Me Mo catalyst , 3 h
Ph
88% (99%e e , S ) Malkov, A.V.; Spoor, P.; Vinader, V . ; KoEvski, P. Tetruhedron Lttt., 2001, 42, 509.
NON-ASYMMETRIC CONVERSIONS S% (113-allyl)PdCI(PPh,) LiCII(C02Me), ,THF
reflux, 13 h
OBz
*T MeOzC
COzMe
61% (955) Krafft. M.E.; Sugiura, M.; Ahboud, K.A. J. Am. Chenz. Soc., 2001, 123, 9174.
S% B(C$,),,
DCM
*
phy 91%
V , Org. k t t . 2001, 3, 2705.
Le Gall, E.;
. .
56%
; NCdClec, J.-Y.; PCrichon, .ITetrahedron . LPtt., 2001, 42, 267.
130
Compendium of Organic Synthetic Methods, Vol 11
BuMgI, ether/PhMe
+
cat CUI (ferrocenyl ligand) rt
Section 68
d 2)
(98 64% ee Karlstriim, A.S.E.; Huerta, F.F.; Muezelaar, G.J.; B k k v
88%
Synlett, 2001, 923.
CHZ(C0zMeh ,BSA ,LDAc chiral amino-phosphine ligand
CH(CD2Me),
1
b
cat IPd(q3-C3H7)C11z , 1 d p h b l u e n e , -20°C Mino. T.; Tanaka, Y.4.; Akita, K.; Anada, K.; Sakamoto, M.; Fujita, T. Tc.tmhedron Asyrnm.. 2001, 12, 1677. Ph
d ph
Ph
,oAc
&SiMe:,
OAc
,rnci3, DCM
YAc
rt,6h
Yadav. J.S.; Reddy, B.V.S.; Madhur, Ch.; Sahitha, G. Cheni. Lett., 2001, 18. OAC I
&
CH(COzMe)2 I
NaCH(COzMeh , THF ,20"C
Ph ph 5%J F't(PPh3)4, 16 h *Ph4Ph Blacker, A.J.;Clarke, M.L.; Loft, M.S.; Mahon, M.F.; Humphries, M.E.; Cheni. Eur. J., 2000, 6, 353.
*L
Raheyrin, C.; Nguefack, C.; Sinou. D. Tetruhedron h t t . , 2000, 41, 7461. -Br m
, I n , aq THF
3.5 h
82%
Ph
82% Yadav. J.S.;Reddy, B.V.S.;Reddy, G.S.K.K. Tetruhedron Lett., 2000, 41, 2695.
13 1
Alkyls from Ethers
Section 69
[;;
cat NiClAdppp) ,THF
60°C
H
H 75% (96:4 fka)
w Ito, ;M. Eur. J. Org. Chcni., 2000, 3393. I
I
.
Er 02C-
CO 2Et
TIIF, 70°C , 4 5 h Ph-0AC
-
p h ~ c 5% Pdz(dba), , O . S PPh3 83% BSA ,AcOK Mordini, A. J. Org. Cherii., 1999, 64, 2962.
o
2
E
qEt
CH(C02Meh
I
Ph
Ph
l-hutyl-3-iI7ethylinid~olilun Ph tetrafluorohorate (ionic liquid)
Chen, W.; Xu, L.; Chatterton, C.;
SECTION 69:
C h m . Commun., Z999, 1247.
91%
ALKYLS, METHYLENES AND ARYLS FROM ETHERS, EPOXIDES AND THIOETHERS
The conversion KOR
Mead
+
RR' (R' = alkyl, aryl) is included in this section.
COzCEf3.8 eq cyclohexylMgBr
-
M LQ
Ph
toluene , rt , 4 h
M O $M e
z
OMe
Kojima, T.; Ohishi, T.; Yarnainoto, I.; Matsuoka, T.; Kotsuki. H. Tetruheclron Lett., 2001, 42, 1709.
90%
t
132
Section 70
Compendium of Organic Synthetic Methods, Vol 11
%
6 4Jg e
B
r ,In,aqT€IP
5h
89%
Kwon, J.S.; Pae, A.N.; Choi, K.I.; Koh, H.Y.; Kim, Y.; fio. Y.S. Tetruhedron Lztt., 2001, 42, 1057.
1. CodCO), , MS 4A 2. Mtoluene gN-0, It
OH
Kajikawa, S.;
60% (1: 1 cis:trans) ; Kumsawa, K. Tetruherlron Lett., 2001, 42, 3351.
OH
dOMe NHChz
Nl lC bz
2 eq Me3Si-
4 q BF3*OEt2
N
I C hz
CIfgI* , 0°C
rt
* & N
I
60% (24:76cis:truns) Chz Matos, M.R.P.N.; Afonso, C A M . ; Datev. R .A. Tc.trulzerlronLett., 2001, 42, 7007.
67% (4654dL:meso) Fujisawa, €1.; Hayakawa, Y.; Sasaki, Y.; Mukaivama. T. Cheni. Lett., 2001, 632.
SECTION 70:
ALKYLS, METHYLENES AND ARYLS FROM HALIDES AND SULFONATES
The replacement of halogen hy alkyl or my1 groups is included in this section. For the conversion of RX -+ RH (X = halogen) see Section 160 (Hydrides from Halides and Sulfonates).
Pd(PPh3)4, Me3SnSnMq
P hBr Br Zhanr.~.; Thomas, L.; Wu, B. J. Org. Cherii., 2001, 66, 1500.
Section 70
133
Alkyls from Halides
3%
n
a-
i - P d ” ON,. r-pr
MqPhSIl ,3% Pd(OAc)2, THF 2 eq TBAF , dioxane Grasa, G.A.; Nolan. S.P, Org.
90%
L&., 2001, 3, 119.
AoMe
1. Me,ZnLiz , 0°C , 2 h
v
82%
2. VO(OCt)Cl2
r
J . Org. Chem., 2001, 66, 300.
’Iakada, T.; Sakurai, 1-1.;
d,C02Bn
DMF , 130“C, K2CO3 , 2 0 h chiral telra-phosphine
97%
OMe
Med Feuerstein, M.; Lhucet. fL,’ Santelli, M. J. Org. Climi., 2001, 66, 5923.
Q
OMe
OMe
I
HSi(OEt), , P d ( d t ~ ,) NMP ~
+
P(t-B u)2(0- hiphe nyl) , i- PrzNEt
Manoso. AS.;
J . Org. Client., 2001, 66, 7449.
Br
I
6 I
Si(0Et
Br
PhB(OII)2 ,3%PdPd(OAc)2,3h 3% DAB-Cy , 2 MI C%CO3 dioxane , X0”C
*
68%
99%
Grasa, G.A.; €Iillier, A.C.;
Org. k t t . 2001, 2, 1011.
Section 70
Coinpendiuin of Organic Synthetic Methods, Vol 11
134
PhOTf , 3 eq C S ~ C O, ~ THF , 18h 9% PdClz(dppf)CH2Ch , EfluX
P hCH2B F3 K
*
PhCHzPh
91%
G . A ; Ito, T. Org. Lett. 2001, 3, 393.
F
\C e/
3
C
PhB(0Hk , Pd/C , 80°C
l
+
F3C@ -h
KzC03, DMNII2O 95%
Le Blond, C.R.; Andrews, A.T.; Syn. Y.: S‘owa Jr, _ ,!& Org. Lett. 2001, 3, 1555. CHO
KOAc, 10 h 2 eq BuoNBr, 10% PCy3
S% PdCI,, 4
87%
C1
ci McClure. M.S.; Glover, B.; McSorley, E.; Millar, A,; Osterhout, M.H.; Roschangar, F. Org. Lett., 21101. 3, 1677. P hB (OH),
--
a t Pd(PPh3)d , rt , ‘II-IF n Cue) thiophene-2carhoxylate
I Savarin, C.;
*
p
h
90%
Org. Lr.tt., 2001, 3, 2149.
PhB(OI1h ,2% Pd(0Ac)z M
e
O
e
\ /
B
Na&03 , aq MeCN, rt t M 2% water soluble alkyl pho.sphines
r
. ~ ,
e
\ / O
~K.II.; .. Booth, R.S. Org. L.ett., 2001, 3, 2757.
ors
e
P
h 94%
PhB(OII), , PCyB 2 q K3P04 ,dioxane
1.S% NiC12(PCy3)2 130°C Zim, D.; Lando, V.R.; Dupont, 1.; m n t e i r o .
Or$.Lett., 2001, 3I, 3049.
94%
Section 70
Alkyls from Halides
Q /
135
z
a t R U C ~ , ( I I ~ - C ~ I - 20 & ) h] ~ ,
a t PPh3 , NMP , 120°C
60%
U;Wkita, S . ; Hirata, N.; Watanuki, N.; Miyano, S.; I n u u e . O r g .
68% Lett., 2001, 3, 2579.
1. PPhR , TBSOTf ,THF 2.h m B r
86%
Lee.; Sung, S.-y.; Lee, K. 81-8.I x t t . , 2001, 3, 3201
03
82% Ph
CdtLlhlnl,;Motti, E.; Baratta, S. O q . Lett., 200Z, 3, 3611. .
I
.
/
/
Rao, M.L.N.; Tamazaki, I.; Org. LJtt.,200Z, 3 , 4103.
PhCI I, C11
BiPh3, K F O ,
*
92%
5% Pd(PPh3)b N M P , 1 0 0 " , Sh ' ; Tanaka,
/
/
T.; Suzuki, Y.;
IISiC13, PEtl, ISO"C, 2 h
Cho, Y.S.; Kang, S.-H.; €Ian, J.-S.; You, B.R.; J. Arn. Clwrii. Soc., 2001, 123, 5584.
Me
t
PhCH, SiCI,
88%
136
Compendium of Organic Synthetic Methods, Vol 11
Section 70
Pyun, D.K.; Lee, C.H.; Ha, 11.-J.; Park, C.S.; Chang, J.-W.; Lee. W.Y, Org. h t t . , 2001, 3, 4205.
SiMe, Me,Si-
4.5%PdC]2(PPh3)2, 16 h 23%PPh3,CuS04,A1203 NEt, , deoxygenated PhII
34% Ph,In, THF , reflux OH
1% Pd(PPhthCl2 , 3 h
-y o P h 0
95%
PCrez, I.; Sestelo, J.P.; Sarandeses. I..A. J. Am. Chern. Soc., 200Z, 123, 4155. PhCH,CI
10 atin C O , PhII , 13O"C, 10 h
*
P hCH,P h 95 %
Qeoshi.;Nakashiinn, 11.; Shimonaka, K.; w s a w a . & J. Ani. Clwnz. Soc., 2001. 12.3, 8626.
PhCl
9-BBN(B-OMe)@ C , 4H2y)X+
*
2% Pd(OAc), ,476 IPr-HCI , THF reflux, 4 h EW&UL-&; Leitiler, A. Syn.lett, 2001, 290. PhBNa , Pd(0Ac)z , MeNIICHO mnicix~waves,12 inin
Ph-(CH2)i3Me
86%
oph 86%
N Y. i l h. u ~ EG6inez-Escalonilla, ; M.J.; Saint-Clair, J.-I.'. Tetruhedron Lett., 200Z, 42, 635.
Section 70
Alkyls from Halides
137
PN miaowaves , 15 niin ;.)I-
.
.
98%
Caillot, F. Tetruhedron Lett., 2001, 42, 630.
76%
Allegretti, M.; Arcadi, A.; Marinelli, F.; Nicolini, L. Synlett, 2 0 0 1 , 609.
P hC1-E2
1. EtZZn, THFINMP
b PhCH2CIIzEt 2. 1130+ Shihli, A.; Varghese, J.P.; Knochel, P.; Marek, I. Synferr, 2 0 0 1 , 818.
75%
(t-BuSiMePh),, ,TIIF
6 0 T ,20 h 67%
Marl.; Suguro, M. Synlert, 2001, 845.
PhB(OH)2 , 2 eq KZCO, a t [PdCl(C,HS)], , 130°C * M tetraphosphine ligand , 2 0 h
e
O
95 %
Feuerstein, M.; Ihucet. 13.: Santelli. M . Syrzlett, 2 0 0 1 , 1458.
(&
+ 2 r g Bu,NI IIong, K.;IIoen, K.;Zhang, J.; Lin, G.-q. Synlett, 2001, 1527.
O
\ /
64) 20)
95% 94%
P
h
138
Section 70
Compendium of Organic Synthetic Methods, Vol 11
u
Br
1. electro-gener~tedZn/NaPh DMA ,-20°C , 1 h
2. PhI, DMF , 70°C, 3 h 5% Pd( Po-T013)2Cl2 . Synlert, 2001, 1944. Jalil, A.A.; Kurvno, N.; C02Et
Ph
COzEt
98%
(-$
Br
Morris, G.A.; Me
*
MQC Osswald, T.; Schneider, S.; Wang, S.; Biuuufarth. W. Tetruheilron Lett., 2001, 42, 2965.
Belllrta.;Anselni,
71 ~ 9 0 % C.; Rossi, R. Tc.trulic~rlronLett.;2001, 42, 3851.
Ilsugi, S.-i.;Yoromitsu, 11.; Oshima. K. Totrulwdron Lrtt., 2001, 42, 4535.
Section 70
Alkyls from Halides
139
PhB(OH)2 , K2C03 , 13O"C, xylene
[Pd(C3115)Cl]z/tetraphosphineligand , 20h
Br
.
Feuerstein,- M .
-.
COzEt
'
Ph
Tetrdiedron Lztt., 2001, 42, 5659.
PhMgCI ,5% Pd(dha)z, 6 h
10% dppf ,TI I I;, -40°C Br Bonnet, V.; Mongin, F.; Trkcourt, F.; QuCguiner, G.; Tctrulierlron LLtt., 2001, 42, 5717.
Ph
,OMe
Zou, G.;
1
THF , cat Pd2(dhaX , 8 0 " ~ NaOAc 2. H20, , NaOH Tetruhedron Lett., 2001, 42, 5817.
69%
PhB(OH), , 5% Pd(OAc), , 8 h 1% Na triphenylphosphinofriwlfonate 2.5 eq LPrzNII , aq McCN, *On; Dupuis, c.;Adiey, K.; Chan.uault, L.; Michelet, V.; Tetr-uh~~drnn Lett., 2001, 42, 6523.
m.M.: G
m
75 %
PhB(OII)z, xylene, KzCOq, 130°C
* I'h-Ph [Pd(C~H~)Cl]~Aet~aphospIiiiic ligltlld Feuerstein, M.; Doucet. H.: Santelli. ryL Tctruhedron Lett., 2001, 42, 6667.
quant
PhBr
Zou, G.; Keddy, Y.K.;
w..1.R. Tetraherlr~onLztt., 2001, 42, 7217. 10%Ni(a~ac)~/Al(acac)~ , NaH
* Ph-Ph 2,2'-hpy1TIIF , RflUx Massicot. F.; Schneider, R.; Fort. Y.; Illy-ChexTey, S . ; Tillement, 0. Tetraherlrnn, 2001, 57, 5 3 1. 2 PhBr
76%
140
Coinpendiuin of Organic Synthetic Methods, Vol 11
0
Section 70
6-f 0
\\
\\
PhB(OH)2 , cat Pd(dha)z cat PPh3, K3P04, 105°C
*
overnight Baillie, C.; Chen, W.;
XiiuJ
0-
83%
\ /
Tetruhedron Lett., 2001, 42, 9085. PhII, 10% Cu(0Tfh
OMS 80”C, 4 h
Singh, R.P.; Kainble, R.M.; Chandra, K L ; Saravanan, P.; Tetr-uhedr-on,2001, 57.241.
81%
m.V . L
, a t Pd(PPh3)d , DME> PhB(0Hk 2M Na,C03
F ’ h q N H 2
73%
NH, NI I2 Cooke. G; de Creiniers, H.A.; Rotello, V.M.; Tmhit, B.; Vanderstraeten, P.E. Tetruherlron, 2001, 57, 2787. PhI, cat Pd(OAc),, 130°C i-PrNEt, , Bu,NBr , xylene
H ~ S S ~J.; I I ,Ilathrouhi, C.; Gozzi, C.;
32% + 21% homo-coupling T m z h d r o n , 2001, 57, 7845.
2% Pd(OAch, 2.5 eq KZCO, B u4NBr
CHO
59% CHO
Syntlwsis, 2001, 755.
Hesse, S . ;
PhSi(OEt), , cat PdC12(MeCNk B
\r /
CF, e
uq NaOI-I, dioxnne
* P
h
e
C
\ /
Murata, M.; Shimazaki, R.; Watanabe, S.; Masuda. Y. Synrlzesis, 2001, 2231.
F
94%
3
Alkyls from IIalides
Section 70
141
-
MeLi , 2 eq Me1 , t-BuOMe DME , 1 0 T , 18 h
Br
93%
Andrews, I.P.; Kitterint..ham. J.; Vogle, M. Synth. Coiimzun., 2001, 31, 2323.
PhB(0II)z , bluene, 130°C Pd-phosphinite complex K2C03,18 h 90%
Bedford. R.B.; Welch, S.L. Clzenr. Coriinzun., 2001, 129.
Br
Goohen.
PhB(OII), ,3%Pd(OAc)z V C O Z E t
9% P(n-Tolh , 5 eq K2CO-j 2 H2O , TI-IF ,20"C
~
,c1 1.5% PdZ(dha)3 , 2.4 eq K3P04*H20 6% feiiocene-phosphine ligand , 70°C
Liu, S.-Y.;Choi, M.J.; Fu. G.C, Chern. Cnmniun., 20111, 240X. PhMgBr , TIIF, r t , 18 h 5% Ni catalyst Bohm, V.P.W.; Gstottmayr, C.W.K.; Weskamp, T.; fIermann. W.A. Angcw. C l i m . Int. Ed., 2001, 40,3387.
10% Ni(acac)slN(acac)3 , N d I 2,2'-hpy, THF ,reflux
-
Ph-Ph
Massicot, F.; Schneider, K.;Fort. Y . ;Illy-Cherrey, S . ; Tillement, 0. Tetruh~~dron, 2001,57,53 1 PhH, reflux , 8 h
C * Z E t
91%
aChrni.Cornrnun., 2001. 669.
2 PhBr
3% Ph V
76%
z PhmzPh 96% 10% LiB(C6F5)4 Mukaiyama, T.; Nakano, M.; Kikuchi, W.; Mutsuo, J.-i. Chwi. k,tt., 2000, 1010.
PhCH,Cl
Section 70
Compendium of Organic Synthetic Methods, Vol 11
142
<
SnBu3
5% PdClZ(MeCN)z, THF , 1 d 10%P(C,Fs), , 5 0 T
SiMe, 87%
Itarni, K.; Kamei, T.; Yoshida, .I.-i. J. Arn. Chern. Soc., 2001, 123, 8773. PhB(0H)2 , toluene , 2 0 h cat P ~ ( O A C,)2~ey BuPAd, K3PO4, 100°C
Gph 87%
Zapf, A.; Ehrentraut, A.; Beller. M. Angew. Cheni. Int. Ed., 2000, 3Y, 4153.
PhB(O1Ik , a t Pd(PPh3)A KZCQ ,NaCl solvent free Nielsen, S.F.; Peters. D.; Axelsson, 0. Synth. Conirnun., 2000, 30, 3501.
F
PhB(OH), ,new Pd catalyst
e C1
Andreu, M.G.; Zapf, A,;
hr
10% Pd(OAc), , 2 0 % PPh, 2 eq PhSi(OMe), , DMF
/
hh 67%
Chern. Cornniitn., 2000, 2475.
2 eq TBAF , 8 5 T
*
85%
/
m; Handy, C.J.; Mowery, M.E. Pure Appl. C h m . , 2000, 72, 1655. hC-@
PhB(OH), , l % P d ( O A ~ ) 2 , 1 8h toluene, 120”C, 10% CsF, 10% P(O-2,4-di-t-Bu-phenyl)3
Zapf, A,;
Cherii. Eur. J . , 2000, 6, 1830.
* F3C+Ph 77%
ph 143
Alkyls from Halides
Section 70
PhOH, reflux , 1 h
PhCH,CI
*
Enviiucat EPZ-10
88% (1:4 o:p)
Kasture, S.P. Monut. Chenz., 2000, 131, 913. PhB(OH)2, K3PO4 2% Pd(OAck, DMF * 13O"C, 1 h
Br
+Ph
76%
Zim, D.; Monteiro, A.L.; w o n t . J. Tetrulzcdron Lett., 2000, 41, 8199.
PhB(0H)z , 10% Pd(OAc);? 83%
P ( O - T O ~ KzCO3 )~, aq acetone, 70"C, 5 h
I
I
SOZPh
SO, P h Liu, Y.; Grihhle. G.W. Tetrahedron L.&t., 2000, 41, 8717.
A
c
\ O/B
r
PhII ,p - x y t n e , 130°C P ~i- Pr2N ( O AECt )Bu4NBr ~,
IIassan, .I. Hathrouhi, ; C.; Gozzi, C.;
P
h
d C1
-
A
c
e
\- /
P
95% Tetrulieclron Lxtt., 2000, 41, 879 1.
10% fenucenyl arnine ligand (r-BuCI12)2Zn , -3O"C, 3 h
*
82% (96%ee)
1% CuBr-SMe2
Okano, K.; Murata, K.;
h
Ph Tetruheclron L d t . , 2000, 41, 0277.
Yin, J.; puchwald. S.L. J. Am. Chent. SOC., 2000, 122, 12051.
98% (87% ee)
144
Compendium of Organic Synthetic Methods, Vol 11
[hmiin]PF6 , 8 0 T t
Ph-F'b
Section 70
87%
a t Ni(PPh3)4 Ihwarth. J,; James, P.; Dni, J. Tetruhedron Lerf., 2000, 41, 10319.
Inada, K.;
NC'
Tetrulwdron, 2000, 56, 86.57, 8661.
-
1. O.SBuMgLi, TIIF, 0°C 2. 1.5 eq T i c 4 , -78°C
0°C 82%
Inoue, A; Kitagawa, K.; Shinokuho, H.;
Tetrulzedron, 2000, 56, 9601.
OMe
I
Br ~
~~
~
1.2 eq Tl2CO3, 6% P c ~ ( P P ~ ~ ) ~ PhH, 100 h
Chauineil. 11.; Signorella, S.; Le Drian, C. Tetrukarlron, 2000, S6, 9655.
Ph -I
cat Pd/C, Z n , HzO , air
-
18-crown-6, rt Venkatraman, S.; Li, C.-J. Tetrulwrlmn Lxtt., 2000, 41, 4831.
ph-&
C02Me
54%
Section 70
Alkyls from Halides
(o-Tol)B(OH), ,THF, rt
O.S% Pdz(hda), , 1% P(t-Bu),
0
3.3 eqKF
d’
145
/
99%
Iittke, A.F.; Dui, C.; Fu. G.C, J.
h i .
Chern. Snc., 2000, 122, 4020.
Bu4N+ (Bn,SnFz)-, DMF
* PhCH,Ph 68% Pd(PPh3)4, 150°C , 1 min Martinez. A.G.; Barcinia, J.O.; IIeras, Md.R.C.;Cerezo, A.d.F. Org. Lett., 2000, 2, 1377. PhOTf
PhBr , 3 % Pd(OAc), ,376 IPI-IICI
PhSi(OMe),
*
2 eq TBAF , dioxane , TIfF , 3 h
P h-Pb
quant
IPr = 13-his(2,6-diisopropyiphenyl)irnklau,lyl-2-y~den~ Org. Lett., 2000, 2, 2053. Lee, 1I.M.;
3
B
r
V Ph
2 As20 , 2 KOII ,80°C 3% PdCl,(dppf) ,dioxme , 2 h
Ph 82%
Chen, 11.; h. M.-% J. Org. C ‘ h m . , 2000, 65, 4444. Br
MeOZC
Shen. W. Synlett, 2000, 737.
Ph
I’hB(0II)z , dioxane , 65°C 2 . S W P 2 ~ ~ ; 15% ~ , TFP
* d
MeO,C
g
9
%
146
Compendium of Organic Synthetic Methods, Vol 11
’
Section 7 0
”/:
2.5% Pdz(dhahCHC13 , CSF 5% dppf , MeCN, 40°C , 10 h Yoshikawa, E.; Radhakrishnan, K.V.; Tetruherirun L.etf.,2000, 41, 729.
76%
OTf
2 q B u B r , PhB(OH), nohornene , Pd(OAc),
81%
DMF , K 2 C 0 3 ,rt
Bu
m . . ; Motti, E.; Minari, M. Cliern. Cnnirizun., 2000, 157.
CN
t
Pd(PPhs)d, NazCO3, 16 h MtCNIH20,9O”C
74%
CO,H Gong, Y.; Pauls, H.W. Synleff, 2000, 829.
dir
COzH
C6H13
1. Bu3MnMgBr
w
2. Me1
Bu
Bu
Kakiya, 14.; Inoue, R.; Shinokubo, H.;
(94 6) 65% Tetruherfron, 2000, 56, 2131.
PhB(OII), , PPh3, dioxane INK-BuLi] , K3P04, IiBr
c1
Me
-
/ Ph
Lipshutz. B.H.; Sclafani, J.A.; Blorngren, P.A. i”efrul7erlron,2000, 56, 2139.
85%
Section 70
Alkyls froiii Halides
2 PhI
NiC12 , QC12 , Mn ,TIIF, rt
147
*
Ph-n
98%
bipyridyl ligiuid , 70 h Chew C. Synlett, 2000, 1491. Me-B- 0, / 0, ,B-Me Me-B- 0
10% Pd(PPh,)4, dioxane * 02N-QMe K2C0, , ivflux
CF3
Gray. M.; Andrews, I.P.; Hook, D.F.; Kitteiingham, J.; Vogle, M.
75%
CF3
Tetruhedron L.ttt., 2000, 41, 6237.
ionic pho.sphine liquid, toluene cat Pd(~Iba)~ , 0.3 h
91%
ML? Synlett, 2000, 1613.
Sirieix, J.; Opherger, M.; Betzemeier, B.; Ph-Br
-
MqSi-SiMe, , 3 % Pd(PPh,), ,DMPU
-
qcl p 9% PPhzFy , 5 eq K2CO3 , 2 H20,lOO"C Feiwanah, A.-R.S. Synlcrt, 2000, 1801.
PhSiMq
w;
5% t-BNi(0) u C 0 2(,CH LiCl J4ZnI ,THF
Me
1214.
*
Ni(0) = [NiC12/2-4 PPh@ BuLfTHFht]
/k(
0
92%
Me L&u&LLL; Blomgren, P.A.; Kim, S.-K. Tetruhcdron L ~ t t . 1999, , 40, 197.
PhBr
0.03 Ni(CO)2(PPh3)2,DMSO
*
70"C, 6 h Leadheater, N.E.; Resouly, S.M. Tetruhetlron Lett., 1999, 40, 4243.
Ph--Ph
75%
148
Section 70
Compendium of Organic Synthetic Methods, Vol 11
,225"C1100 har aqueous Bu4NCl 40%
Heck reaction - in aqumus media
67: 13:20 l-Ph:2-Ph:3-F'h-cyclohexene
Cron.; Tinsley, A S . Tetruhedron Lett., 1999, 40,227. ICH,CO2Et, NaZS2O3 B u ~ N BC-BuOMe ~, ,hv N
rn I
COzEt N
*a I
ineth yloxirane
90% H Bvers. J.H.; Cunphell, J.E.; Knapp, F.H.; Thissell, J.G. Tetruherlron L ~ t t .Z9Y9, , 40, 2677. €I
Br
H
&SnBU3 0.05 Pd(PPh3)4 , 0 . 2 CUI 60°C , DMF , 3 0 min
H
Denhlda.; Lecubin, F.; Fouirey, J.-L.; Castellanos, L.R.; Quintero, L.
92%
Tetrultc~dronIxti., 1999, 40,5701.
Mero, C.L.; porter. N.A. J. Ant. Client. Soc., ZYYY, 121, 5155.
79%
CIfO
$5
c1 ;-
c1-Zn1
5% Ni/C , PPh3 , THF
*
c&aro
Blomgren, P.A. J. Am. Chern. Soc., l Y 9 Y , 121, 5819.
\ /
80%
Section 70
Akyls from Halides
149
,I
1. BuLi, THF, -50°C 2. Cp,ZiCMe/CI , bis-phosphine
Me
-
-50°C rt 3 . Cat Pd~(dha)3, Br 60°C 4.1, , CHZCI,
64% (m:o = 8 0 1) Frid, M.; Perez, D.; Peat, A.J.; B u c h w u J. Am. Clieiii. Soc., 1999, 121, 9469 Sc(OTf)-\ , PhH
92%
Ph
S O T ,4 h
several other catalysts used as well
Kotsuki.;Ohishi, T.; Inoue, M.; Kojiina, T. Synthesis, 1999, 603. 1 0 % Pd(dha), , 5 eq Ph3SiFz
DMF,5h
Mowery, M.E.;
,nv
(CSHi1hZn,THF/NMP
I
Ph
T
86%
P, J. Org. Clwni., 1999, 64, 3266.
*
7%)Ni(acach , -35T
csH Ph
80%
Giovannini, R.; Studemann, T.; Devasagayaraj, A.; Dussin, G.; Knochel. P. J. Org. Chc~rii..1999, 64, 3544.
@-
PhB(OH), , HZO 2.5 KZCO,
on
>
mt Pd(0Ac)z miaxow aves
Lettner. C..G.; Kiinig, W.A.; Stenzel, W.; Schotten. T. J. Org. Cheni., 1999, 64, 3885.
0
Ph- B(OII), , H 2 0 , rt
Br BudBr, 2 h Bussolari. J.C.; Rehhorn, D.C. Org. I A t . , 199Y, 1, 965.
O
P
h
45%
150
6
Section 70
Coinpendium of Organic Synthetic Methods, Vol 11
Br
Br
C02Me
%08 ' $ C02Me
Shen. W.; Wang, L. J. Org. Cl~cwz.,Z9Y9, 64, 8873.
SiMe,OI-I
PhI, Cat Ph(PPh,)4 * Ag20,l'HF ,6O"C, 36 h
M
e
O
O
\ /
P 80%
h
Hirahayashi, K.; Kuwashuna, J.; Nishihara, Y.; Man.; Hiyama, T. Org. Lett., 1999, 1, 299. 8% Pc/C , air, Zn , overnight
P h-Ph
94%
+ Ph-Ph 50% hydroquinone IIennings, D.D.; Iwarna, T.; pawal. V.H. Org. Lett. 1999, I, 1205.
96%
P h-I
b
HZO/acetone, rt Venkatranian. S.; 1.i. C.-J. Org. Lett. Z999,1, 1133.
Ph-I
2% Pd(OAc), , 2% As(n-Tol)3 C ~ 2 C 0 3,0.4M , 7 5 T , 3 h
P h 3 h , TI-IF, flux cat PdC1APPh3), , 1 h
A
Perez, I.; Sestelo, J.P.; Sarandeses. L.A. Org. Lxtt. Z9Y9, I, 1267. B d n B r , Pd(dha)z, 2 h dppf , Bu4N1, T I I F , 60°C
Piher, M.; Jensen, A X . ; Rottlinder, M.; b c h e l .
Org. Lc?tt., 1999,1, 13223.
94%
Section 70
Alkyls from Halides
15 1
10%Pd(PPh3)4, NMP 80"C, 3 h
80% Et
Rao, M.L.N.; Shimada, S.; 0
W
0
1
Org. Lett. 1999, I , 1271. b
2
, 5 % Pd" , KF
* G neat, A120, ,80"C Kahalka. G.W.; Pagni, R.M.; Hair, C.M. Org. Lett., 1999, 1, 1423. PhI
OBr
P
h
"%
10%Pd(OAc)z, 20% PPh3
PhSi(OMe), , 2 eq TBAF DMF , 8 5 T Mowery, M E . ; DeShong. L O q . Lett., 1999, 1 , 2137. 2
82%
o\
PhB(OI32, K2CO3 , reflux c1
5% Ph(PPh3)4,8 h toluene&IPIEtOH
N
Ph
80%
I,ohse.; Thevenin, P.; Waldvogel, E. Synlett, 1999, 45. 2.5%PdCl(x-GHS), , DMSO
Ph-I
Ph-Ph TBAF, 120"C, 4.5 h A l b m e . D,; Landini, D.; Penso, M.; Petricci, S. Synlett, 1999, 199.
0
82%
PhOTf , Pd2(dhah*dha, D M F
12% c h i d hiaryl bis-phosphine * QPh 3 eq i-Pr2NEt, 90°C. 20 h Tietze. L.F.; Thede, K.; Sannicolh, F. Chcwi. CO/?l/l?I4n.,1999, 181 1.
Me( CH &XCH,Cl Alonso, F.; Radivoy, G.;
NiC12-2 H2O ,Li , 5 % dThh
*
90% (90% ee)
Me(CH&&H,H
dTbli = d,4'-di - t- hut ybiphe ny 1 Tctruheclr-on, 1999, 55, 4441.
55%
152
Compendium of Organic Synthetic Methods, Vol 11
Section 70
BuI , e - , 70"C, T H F , 3 h Pd[F'(o-Tolh]zClz electmgenerated reactive Zn OMe Jurono, N.; Sugita, K.; Takasugi, S.;
.
79% OMe Tetruhedron, 1999, 55, 6097.
GBr
PhB(OH), , dioxanc , 8 h NiCl,(hipy) , Na,P04 70%
LeddtLdter.; , 11, Resouly, S.M. Tetruhedron, IYY9, 55, 11889.
Ma, H-r.; Wang, X.-h.;
59% toluene, 85°C Synth. Conziiiun., 1999, 29, 2477.
MnACOha, DCM hv 88% Gilhcrt, B.C.; Lindsay, C.I.; McGrail, P.T.; J'arsons. Syntlr. Coiiiiiiun., 1999, 29, 271 I. 1. BuLi, THF 2.BF3
\
3. PhBr , PdClz(PPh3h
+ D
P
\
Me Me Lshikura. M.; Agata, I.; Katagiri, N. J. Heterocyclic Chena.. 1999, 36, 873.
h 80%
Section 7 1
SECTION 71:
153
Alkyls fivm Hydrides
ALKYLS, METHYLENES AND ARYLS FROM HYDRIDES
-
-
This section lists examples of the reaction of RH RR' (R,R' = akyl or aryl). For the reaction C=CH C=C-R (R = alkyI or aryl), see Section 209 (Alkenes from Alkenes). For alkylations of ketones and esters, see Section 177 (Ketones from Ketones) and Section 113 (Esters from Esters).
96% (80%ee) Chieffi, A.; Kamikawa, K.; Ahman, J.; Fox, J.M.; Buchwald. S.L. Org. Lett. 2001, 3, 1897.
0 OIIPS
H.M.L.;Ren, P. J. Am.
(65 : Chenz. Soc., 21101, 123, 2070.
35) 80%
10%[Mo(CO),(EtCN),] , 70°C lS% chiral diamine ,NaH, T H F
Ph
CII*(CO2Me)2 , 3 h
Ph
*a 70% (99% ee)
Glorius, F.; Neuhurger, M.; .&&&L Hclv. Chim. Actu, 2001, 84, 3178.
h & W O r , hoton Sponge Me,Si
-20°C
Me3Si
An =p-(MeO)-C,HjIIerrlich, M.; I-Iampel, N.; Org. L m ,2001, 3, 1629.
CHAnz
53%
154
Section 71
Compendium of Organic Synthetic Methods, Vol 11
0 N
*o
1. 1.3eq sec-BuLi, 1.3eq diarnine -78"C, 5 h
I
I
41% (53% ee)
Boc
B oc
Harrison, J.R.;
s &fe3
""UII,
N
2. MqSiCl ; Porter, D.W.; Smith, N.M. Cheni. Commun., 2001, 1202.
1. PhOCOCl , EtMgCl CuBr-DMS ,TIIF
C%Et
2. DDQ , i-PlOAc
&
C0,Et
*
44%
N Wallace. D.J.; Gihh. A.D.; Cottrell, I.F.; Kennedy, D.J.; Brands, K.M.; Dolling, U.H. Syntlwsis, 2001, 1784. cat ReBr(CO)S , t-BuC1* DCE,84"C ,301nin
.
0
t
0
o
t
\ /
+
.. . m; Kakushou, F.; b ,
E
-
B
"
63%
35% 2,Gili-t-Bu)
d a. N,Bull. Chmn. Soc. Jpn., 2000, 73, 2779.
.A%,, N
1% Rhcatalyst with DOSP chiral ligands
Pavies. 1I.M.L.; IIansen, T.; Churchill, M.R. J. Ant. Chem. Soc., 2000, 122, 3063.
COZE t
-0Ac
7
K2C03
1% Pd(PPh,), ,30"C
S% T i i t O X - 1 0 0
ncl
K d.x.y. d ~ LLam, ~ . ; W.W.-L.; Manahe, K. TetruRedron Lett., 2000, 41, 61 15. 1. 3 eq BuLi-MqNCf12C€120Li hexane, -78°C 2 . 4 eq Me1 ,THF , 1 h C1 -78°C -5. 0°C Choppin, S.; Gros, P.; Fort. y. Org. Lett., 2000, 2, 803.
Me
70%
155
Alkyls from Ketones
Section 72
Elliott, (3.1.; Konomlsk . i. J.P.: Olmstead, M.M.
01-6'.
Lctt., 1999, I, 1867.
Sih4e3
LSiMe3 Ph
6 eBr -6" ' Ph
Lenges, C.P.;
88%
5% Rhcatulyst
J . Aim Chern. SOC., 1999, 121, 6616.
,Na , Py,CuC12
ether
Tan.;Zheng, X.; Ma, Z.; Gu, Y. Synth.
SECTION 72:
A
66% (40160 o/p) 123.
ALKYLS, METHYLENES AND ARYLS FROM KETONES
?be conversions R$=O
Ph
Coiiinticn., 1999, 2Y,
-
R-R, RzC€I?, RzCHR', etc. are listed in this section.
T i c 4 , toluene ,reflux
*
/4
Ph
Li, Z.; Sun. W.-H.; Jin, C.; Shuo, C. Synlett, 2001, 1047
Ph
65%
Section 74
Coinpendiuin of Organic Synthetic Methods, Vol 11
156
B(i-Pr)z $1
P h&CO
, ether
4 eq NaHCO3 , overnight -1O"C-. It
65%
Xahalka. G.W,; Yang, K.; Wang, Z. Syntlz. Coninrun., 2001, 31, 511.
L
m S i M e 3
+
67%
HSiMe,Cl , DCM , r , 2 h
Ph Yasuda, M.; Ohishi, Y.; Ito, T.;
SECTION 73
, 5 % 1IlCl3
Ph Teti-uhrclron Lrtt., 2000, 41, 2425.
ALKYIS, METHYLENES AND ARYLS FROM NITRILES [PhMgCi , t-BuOK, TMF 60°C. 1 h]
i
M
t
5 % CI2Ni(PMq)2, 6O"C, 1 h
M l l l e r . T e t r u l t e t l m n k , t t . , 2001, 42, 6991.
Zhu.;Shia, K.-S.; Liu. H.-J, Tetr-uh~~cli-nn L.ztt., 1999, 40,7055.
SECTION 74:
\ ) /O
K
P
91%
80%
ALKYLS, METHYLENES AND ARYLS FROM ALKENES
The following reaction types are included in this section:
A. B. C. D. E. F.
Hydiagenation of Alkenes (and Aryls) Formation of Aryls Alkylations and Arylations of Alkenes Conjugate Reduction of Conjugated Aldehydes, Ketones, Acids, Esters and Nitriles Conjugate Alkylations Cyclopropanations, including halocyclopropanntiotis
h
157
Hydrogenation of Alkenes
Section 74.4
SECTION 74A: HYDROGENATION OF ALKENES (AND ARYLS) Reduction of aryls to dienes are listed in Section 377 (Alkene-Alkene).
ASYMMETRIC HYDROGENATIONS enzyme NAD PH YNAR-I= PhLNo2
-
-k
-
Ph%Noz
(2 3) 31% >98% ee) >97% G% Kawai. Y.: Inaha, Y.; Hayashi, M.; Tokitoh, N.Tetruhedron Lett., 2001, 42, 3367.
phTNo2 Bakers yeast, glucose, 7 h
EtoII , ri20 * p h 7 N T 2 % (17%ee, S ) b w a i . Y,; Inaha, Y.; Tokitoh, N.Tetruliedron Asynzm., 2001, 12, 309.
Filho, E.P.S.; Rodrigues, J.A.R.;
I
Tetruhedron Asymm., 2001, 12, 847.
Am2Me + A CW2Me
Hz ,cat [ R ~ ( C ~ ~ X S - B I N MBF, O)]
Ph
NH Ac
Zhang, F.-Y.; Kwok, W.H.;
DCM, 10 min
,
C02Me Subrez, A.; W m o ,
NHAc
quwt (84% ee) Tetruliedron Asynim., 2001, 12, 2331.
HZ ,DCM ,fl [Rh(codXWP)] BF, Me02
Ph
*
Me02
C02Me
POP = phosphine-phosphite ligand
4. Tetruhedron Asyrnni., 2001, 12, 2501.
99.8%ee
158
Compendium of Organic Synthetic Methods, Vol 11
Section 74A
polymer- suppoiterl BI NAP Ru@INAP) , MLOH
Hz , NEt,
a
ML O Fan.; Deng, G.-J.; Lin, C.-C.;
‘
I
quant (96% ee) Me0 Tetruhedron Asymm., 2001, 12, 1241.
B a k e s yeast 14h
* 12% (>99% ee , s)
KdWdi.; . . Hayashi, M.; Tokitoh, N. Tetruherlron Asynzni., 2001, 12, 3007.
I
I
50 bar H 2 , cat Ir(cod)-chid oxamline
Ph
DCM
Ph
Blankenstein, J.; Pfaltz. A. Angew. Chenz. Int. Ed., 200Z, 40, 4445.
0 *N Ph
[Rh(P-P*)(cod)] BF, ,MeOH 50 bar IIz ,It
P--P* = chiral his phosphine
*ci “t
Tararov, V.I.; Kadyrov, R.; Riermeier, T.H.; Holz, J.; Borner. A. Tetruhedron LEtt., 2000, 41, 2351.
CQMe
=-L
quant (97% ee)
Ph
>99% (up to 50%ee)
[Rh(codh] PF6, DCM, rt phosphine ligand, 1.3 bar H2
COzMe
Reetz.; Mehler, G. Angew.
rt,20h quant (97.6%ee) Chenz. Int. E d , 2000, 3 g 3 3889.
Hydrogenation of Alkenes
Section 74A
159
1% [Rh(cod),]PF6 , 1.1%chird his phosphine
*
3 atinH2, MeOH , rt, 12 h
NHAc
4a2H NIIAc
quant (>99% ee) Tetruhedron LEtt., 1999, 40, 6701.
Li, W.; Zhang, Z.; Xiao, D.;
RR-(EBTHI)-ZrMe2,1700 psi Hz [PhMqNH]' @3QF,]4It, 13-21 h
EBTHI = e~ylenehistetrahydroiiidenyl Troutman, M.V.; Appella, D.H.; COzMe Ph
NHAc
87% (93% ee; >99:1 cis:tmm) J. Am. Chem. Soc., 1999, 1221, 4916.
1% adamantyl-his-P*, MeOH I12,rt,2h
NHAc
Ph
99.9% ee ,R
o. T, Org. Lt~tt.,2001, 3, 373.
*M MLoq NON-ASYMMETRIC HYDROGENATIONS Hz , Pd h h c k ,PhH 4h
-
MeO
MeO
quant
Makl.; Okawa, M.; Matsui, R.; IIirano, T.; Niwa, II. Synlett, 2001, 1590. t-BuNIIZ.BII3 , 10% Pd-C MeOII, sealed vessel
mPh
ph * Ph rt , 4 h Couturier.; Andresen, B.M.; Tucker, J.L.; Dubt, P.; Brenek, S.J.; Negri, J.T. Tetruhcrlron LEtt., 2001, 42, 2763. Ph
Ph&COZH
cat RhCl(PPh3)3, DMSO mimwaves Desai, B.; Danks. T.N. Tetruhedron Lett., 2001, 42, 5063
-
Ph
93%
C4H 95%
-
160
-
Compendium of Organic Synthetic Methods, Vol 11
Ph
Et,SiH, TFA ,-10°C
NHC02Et
Masuno, M.N.;
*
30 min *
Tetruhedron .Lett.. 2001, 42, 8263.
Section 74A
NHCO2Et
Ph
94%
inhexane (24 76) (88 0) in DCM Ilodeson. D.M.; Barker, S.F.; Mace, L.H.;Moran, J.R. C h m . Commun., 2001, 153. Rh-his-phosphine catalyst 0 on mesoporous silica H2
Crudden. C.M.; Allen, D.; Mikoluk, M.D.; Sun, J. Cheni. Cornmun., 2001, 1154. OH
cat [RhC1(1,5-~0d)]2, 10 b~
H2
1120 , supcwiticd ethane, 62 h
0.1M Na3P04, cat Bu4NHS04 36°C Bonilla, R.J.; James, B.R.; b p . P.G. Cheni. Cotnmun., 2000, 941.
Tsukinoki. T.; Kanda, T.; Liiu, G.-B.; Ysuzuki, H.; 'fashiro. M. Tetrulidron Lrtt.. 2000, 41. 5865.
+ \
Ph
Yakahe, S.; Hirano, M.;
A/
Ph
NaBH4, NiCl2.6 HzO , hexane
quant
94%
Ph moist A203 Tetruliedron Lett., 2000, 41, 6795. €I2 , R,R-Me-DuPhos-Ru t-BuOK, i-PrOII
* Ph&
--
90%
92% (86% e e , R)
Forrnan, G.S.;Ohkuma, T.; IIems, W.P.; Novor i. Is, Tetrulierlron L.ett., 2000, 41, 9471.
Section 74A
Hydrogenation of Alkenes
161
5% P d C l (ethylenedianiine)
Hz ,TtIF Hattori, K.;
Tetrahedron, 2000, 56,8433
'
YL 0
PhO
LYk 0 PhO
IICOzN€14 , Ni(R) ethylene glycol
mimowaves , 3 inin Banik, B.K.; 0 Barakat, K.J.; Wagle, D.R.; Manhas, M.S.; . J. Org Clwm., 1999, 64, 5746.
H, (60 atmn) ,9O"C ,3.Sh [hmim] @I$] ionic liquid
0
*
91%
[H4RU4(r16-%b)41 [ B h ]2 Dyson, P.J.; Ellis, D.J.; Parker, D.G.; Welton, T. Chf,/n. Commun., 1999, 25.
EtvcozEt 1.2qG
C0,Et
M
S
r
Ir
ether, reflux, 3 h 2 . 4 NHACl
Kim, Y.M.; Kwon. T.W. ; Chung, S.K.; Smith, M.B. Synth. Cornmun., I999, 2Y, 343.
COzMe
cat RUClZ(PPh3)3 , 12 h K 2 C Q , toluene, reflux
* P BdsdVdldk~.; , .. . . Muthukumaran, K. Syntk. Conzmun., Z999, 29, 713.
C02Me h
5
53%
Section 74B
Compendium of Organic Synthetic Methods, Vol 11
162
SECTION 74B: FORMATION OF ARYLS AND HETEROARYLS
MeOf-Bu , -20°C H 89% Tilstarn. IJ,; Harre, M.; Heckrodt, T.; Weinmann, H. Tetruhedron LEff., 2001, 42, 5385. 2% PdClZ(MeCN)z, 2 h
5 wa. L; Uedo, E.; Tan, R.; &&-&
NEt3, MeCN
-
ONCl
J. Org. Cltem., 2001, 66, 186.
Br
89%
Br Ph
Hu, J.-h.; Zhao. G.; Yang, G.-s.;Ding,
98% (94.2% ee , R)
J. Org. Chem., 2001, 66, 303. Me0
Mg Br
0
Mohanta, P.K.; Peruncheralathan, S.;
THF,rt,3 h
-
2. BI;,*OEtz, MeNOz 0°C rt , 12-15 h
H.: J
.
SMe w J. Orb. Chem., 2001, 66, 1503.
Section 74B
163
Formation of Aryls
1. (CHzO), , KOH , MeOI-I 2. Cu(0Acb , NIIdOAc AcOH Pilato, M.L.; Catalano, V.J.; Bell. T.W. J. Org Cltern., 2001, 66, 1525.
GHII
Li, J.; Jiang.
PdClz PhII,,40"C, CUCIZ12 , BuOH h
-
64x91%
C 5 H 3 7 " ' -
*
H.;Chen, M. J.
c5H 11
Org. Chetn., 2001, 66, 3627.
1. BuLi, THF, rt 1 h , PdCMPPh3h
-
EfO-(Cozn
C0,Et
DMSO ,PhI 2. KOt-Bu ,THF G q o n , S.; Vassiliou, S.; Cavicchiioli, M.; Hartmann, B.; Monteiro, N.; J. Orx. Chein., 2001, 66, 4060.
a,
J'vlaarcoux. J.-F.; Marcotte, F.-A,; Wu, J.; Dormer, P.G.; Davies,
J. Org. Chmt.. 2001, 66, 4194.
Ph 0
(- \hp
Pd(OAcb, NEt3 THF
*
53%
0
84% I.W.; Hughes, D.; Reider, P.J.
54%
PI1
Jeevanandam, A,; Narkunan, K.; b g . Y.-C, J. Org. Client., 2001, 66, 6014. 1.
"y"' 'Iro
COZEt CO ZH
2. CICOZEt , NEt, 3. NaOII, EtOII
,50"c,12 h
p
h
A
* Br
Serra.; Fuganti, C.; More, A. J. Org. Cliern., 2001, 66, 7883.
COzEt 70~78%
164
Section 74B
Compendium of Organic Synthetic Methods, Vol 11
~
\
~
,
t
-
B 5% u Pd(0Ac)z. Ph-pPh 10% PPh3
/
5
NazC03, DMF , 1 d 100°C
Roesch, K.R.; Zhang, H.; Larock. R.C. J. Org. Chenz., 2001, 66, 8042.
+
Me, Si
Atienza, C.; Mateo, C.; de Frutos, 0.; '.
+
NMe2
Y
Org. Lett., 2001, 3, 153.
0 L C o z M e
C1
,TIlF
M a 2 m c 1 ; 8 %
20% t-B uOK , D A B 0
N+
I
. NMez .
Davies. I.W., M.ucoux. J.-F.; Reider, P.J. Org. Lett., 2001, 3, 209.
Amii, H.; Kishikawa, Y.;
Org. Lett., 2001, 3, 1109.
Ph
Ph 0
0-
NH4' HCOZ-, 10% P d C PEG200 , microwaves 30 s e c
* Ra
Rno.; Jothilingam, S. Tctruhdron Z ~ t t . ,2001, 42, 6S95.
p
N H
b
92%
Fonnation of Aryls
Section 74B
7
HN\
165
aoMe Nq @ ' I
*
83%
cat Pd,(dba)3/P(2-filryl)3
NaOt-Bu, ?'HI;, 5°C MeCN. 40°C
Ph Arcadi, A,; &chi.
Ph
S,; Casciu, L.; Lahrizi, G.; Mnrinelli, I;. Org. Lett., 2001, 3, 2501.
*
inin 150"C, 20microwaves
/c%,
40%
Diaz-Ortiz. &; tle la I-Ioz,A.; Prieto, P.; Camllo, J.R.; Moreno, A,; Neunhooeffer, H. Synlett, 2001, 236.
"ZEt
2 eq E t N 0 2 , DMF, 17h 3 eq K2C03 , rt + 50°C
m:
75%
&m. J.N.; Im, Y.J.; Gong, J.H.; Lee, K.Y. Tetruherlron Lett., 2001, 42, 4195.
hOMe Me02
PI1
0
0
NaOMe , MeON ,70"C
*
UB.; Jones, A.B. Tetrullcvlron Lxtt., 2001, 42, 6429.
dioxane , 100°C
Jackson, T.J.;
Tetruheclron, 2001, 57, 3859
72%
Bu OMe
57%
166
Section 74B
Compendium of Organic Synthetic Methods, Vol 11
1. acetone, 2 eq Sm12 , TIIF 20T, 6h
,GH7
Ph+ N
Ph
2. 1MHCl
0
Farcas, S.; u v . J. -LTetruhedron, 2001, 57, 4881 .
Etozm 0
Wu, Y.-L.; Chuane. C.-P.; Lin, P.-Y. Tetruhedrnn, 2001, 57, 5543. C0,Et
H
I
b
M C3H7
e 84%
0
NO+/ 18-crown d/H( NO3)2DCM,rt
Zolfieol.;Zeharjadian,
M.I.I.; Sadeghi, M.M.; Moharmnadpoor-Baltork, I.; Memarian, H.R.; Shamsipur, M. Synth. Cnnzmun., 2001, 31, 929.
t"n C02Et
BaMn04 , PhH ,~ f l u x ;.-
E'"n , .
95%
H Sadeghi, M.M.; Momeni, A.R. Synfh. Cornmun., 2001, 31, 2241.
cop
FeCh.6
H20
,reflux
aq AcOH , 1 h
I1
U;Bai, Y.; Wang, 2.; Yang, B.Q.; Li, W. Synth.
60%
Coritnirin., 2001, 31, 2625.
NalISO,, HZO , wet S O z
H Damavandi, J.A.;
'>
Na2Cr20y2 H 2 0 , DCM * rt . 10 tnin ; Karami, B. Synth. Cornniun., 2001, 31, 3183.
97%
Section 74B
Formation of Aiyls
167
fi
EOZC PhI(0Ac)z , DCM
COZEt
MeHN
&,2h
P
Zhang, P.-F.; &n.
87%
Z.-C. Synth. Conintun., 2001, 31, 1619.
\
Ph
*
COZEt
2S eq %rBPd(PPh3)4,5O"C, -/ , 2 12 eqZiBrz h *&h
/
Ph
Duan, Z.; Nakajima, K.;
.,
/ 59%
Cheni. Comrnun., 2001, 1672.
acetophenone, KOH cat Gruhbs'catalyst , 80°C
00. C.S.; Kim, B.T.; Kim, T.-1.;
. Chent. Contmun., 2001,
,N
Ph
2576.
a t Pd(PPh3)4 , DMF
B u f i C l , 80°C
Tsutsui, 1-1.;
Clrern. Lett., 2001, 526.
1. pipmidine, AczO, 85°C EOAc , toluene , 1 h * 2. 150°C. 3 h
Wei, L -L.; IIsune. R.P.; Sklenicka, H.M.; Gerasyuto, A.I. Anxew. Clteni. Int. Ed., 2001, 40, 1516.
77%
80%
Compendium of Organic Synthetic Methods, Vol 11
168
Section 74B
Ph
I
Ph hv , hexane Ph
Ph
w; Cam, M.; Rodriguez, M.A. Tetmherlron Lctt., 2001, 42, 3575.
82%
S . ; Oh, D.H. J. Heterocyclic Chetn. 2000, 37, 1315.
Cho, C.S.; Oh, B.H.;
Br ,THF . Et
cat NiCl,(PPhs)* Et
Wang, H.; Tsai, F,-Y.;
'
43%
Et Et
TN
Cheni. k t t . , 2000, 1410.
1. B uNI ILi ,T I IF 2. aq IT
*
CN
/
BU
Wang, A.: Zhang, H.; Biehl, E.R. Heterocycles, 2000, 53, 291.
NaNO,, C2H204*2fIzO
CO2Et b
98%
DCM , wet SiO, ,it
H
93%
/N
u '> Kiany-Borazjani, ; M.; Sadeghi, M.M.; Mohairunadpoor-Baltork, I.; Memarian, 1I.R. Synth. Comri~nn.,2000, 30, 551. N-01 I Ph
Ph
DMF , POCb ,90"C
*
q::
Amaresh, R.R.; J'erurnal. P.T. Synth. Corntnun., 2000, 30, 2269.
19%
Fonnation of Aryls
Section 74B
Selvi, S.;
Synth.
Coitiiiiun.,
169
CHO
2000, 30, 3925.
2%PdI2-KI, 100°C
Ph
dimethylacetamide
SH
58%
Gahriele, B.: Salenio. G.; Fazio, A. Org. Lett., 2000, 2 , 351.
Bu M%NC02t-Bu
1. sec-BuLi, (-)-spaitcine, TIIF, -78°C 2. CuCI.2 LiCl, -55°C
* Bo-X0
3.
fiter.
h
I
Me
Me
u; Yu, H. Or$. Lett., 2000, 2, 2283. 'jMq
oTf
&''
N
M
e 64~79%
, CsF , MtCN/THF
10% Pd?_(dha),*CIICl~, 20% dppf 60°C
Yoshikawa, E.; Radhakrishnan. K.V.;
J . Ani. Chciii. SOC.,2000, 122, 7280.
Me, Si
Ph
.$
SiMe,
MeLi , toluene
SiMq Brunette, S.R.;Lipton.
aJ.
Org. C h m . , 2000, 65,S114.
44%
Section 74B
Coinpendiutn of Organic Synthetic Methods, Vol 11
170
Shanna, U.; Ahmed, S . ;
Tetruhedron Lctt., 2000, 41, 3493. 1 . EtNO, , KZCO3 , H2O -6O"C, 1 d
0
2. toluene, i ~ f l u xair , 0
90~53% . . Balllnl.; Barhoni, L.; Bosica. G. J. Org. Chem., 2000, 65, 6261.
phE
P d ( 0 . 4 ~ PPh3, ) ~ ~ CUClz
*
Qy-,
N K2C03.1 d 46% Bt Bt = henwtriazyl Ph Katntzkv..;Zhang, L.; Yao, .I.; Denisko, O.V. J. Org. Chent., 2000, 65, 8074.
I
2% AlCl3 , MtCN ,20"C 65%
t
OH ; Frost, T.M.; Bats, J.W. J . Am. Chent. Soc., 2000, 122, 11553.
Cho, C.S.; Kim, J.S.; Oh, B.11.;Kim, ?'.-J.; Tetruherlron, 2000, 56, 1147.
s PI1
; Yoon,
, Ag2CO&elite
MtCN ,reflux 0 Lee.;Suk,
'
*
J.Y.; Kim, B.S. Org. Lett., 2000, 2, 13x7.
N.S.
57%
@
51%
Section 74B
Fonnation of Aiyls
171
1. HOCHzCOzEt , PPh3 DEAD, T€IF 2. NaIi, THF
c1
NC
C0,Et
*
'-"'*
80x88%
-d NH*
an. A M ; Dumas, J.; Scott. W.J. Org. Ltrt., 2000, 2, 2061.
/-
L
PhCIcII , DCM , sealed tube 5%J GlUbbS' Cakllyd, 40°C
N
Ts-
Ts-
82% (5:ltnei?~Me:orfho Me) Wltulski.; Stengel, T.; Fernindez-Hernandez, J.M. Chenz. Cnnimun., 2000, 1965.
BnNH2, EtNO,, SO2 Ph*CHO
microwaves, 5 min
2.3 N
I
Bn
panu. B.C.; IIajra, A.; Jana, U. Synlett, 2U00, 75.
. R.C.;
51%
Ahmed, S.; Sharina, U.; Sandhu, J.S. J. Org. Chenz., 2000, 65, 922.
ph
PdC12(MeCN),
74%
+
THF , 10°C ~
F
I
,
60%
Ph
Gao, ; W.-Z.; Ying, .I. J . Org. Cheni., 2000, 65, 2003.
1. DCM, heat
2. MnOz, PhH reflux , 4 h
.
.
Kircher, G.; Willems, M. J . Org. Chem., 2000, 65, 2370.
0 53~61%
172
Coinpendiuin of Organic Synthetic Methods, Vol 11
Section 74B
,PhH, reflux Catp-TsOII, 3 h
AcO
Wang, C.;
PhIi, r t , 18 h Org. L.ett., 2000, 2 , 1773. KMnO3-AI2O3, acetone 0°C. I h
McBride, C.M.;Chrisman, W.; Harris, C.E.;
pillladacycle catalyst
Ph
NEt, , T H F , rt
Tetruheclron Lett., 1999, 40, 45.
* ( 3 1 1
83%
Luo. F.-T.;Jeevanandam, A.; Bajji, A.C. Tetruhedrori Lrtt., 1999, 4 0 , 121.
CBH/ = C3EI7 , MeCN 5% Pd(OACX, 5 % ~P(O-TOl),
CsF ,60"C, 4 h
Radhahishnan, K.V.; Yoshikawa, E.; y;bmsm
1.
B-Et
, p h ~ f ~
cat Ni(acac)2/PPhB/A1Mq 2. DBIJ , air
WEt
Mori, N.; Ikeda. S.-i.; Sato, Y. J . Ant. Clieni. Sor., 1999, 121, 2722.
'
Et
Et 60%
Foimation of Aiyls
Section 74B
= =
Bu
173
Bu
5% Pd(PPh3)4, TIIF -van. V.; Takeda, A.a.; Homma, M.; Sadayori, J. Am. Chem. Sac., 1999, 121, 6391.
Kadotn, J.; Komori, S.; Fukumoto,
N/
t-Bu
BU
Bu
Y.;Murai. S . J. Urg. Cliern., 1999, 64, 7523.
1. P h G C H , 2 % PdC12(PPh3)2 1% C U I ,NEt, , 55"C, 2 h 2. lOO"C, 10 CuI , DMF , 1 h 91%
Roesch, K.K.; Lartrck. R.C. Orx. Lett., 1999, I , 553.
MtOII, 50°C
*
/
/
Ph Suginome, M.; Fukuda, 'I'.; Ito. Y. Org. Lett., 1999, 1 , 1077. 0.5
Ph
Nll2
CHO
hv ,PhH , 5 h
Ph Qda.; Nkagami, R.; Nishizono, N.; Machida, M. Chmi. Critnmun., 1999, 2371.
1. THF , t-BuOK , 0°C
2.0.lMIIC1,O"C
&Gee.
u: Leach, J.D.; Setiadji, S . Tctrulierlmrr, 1999, 55, 2847.
86%
Compendium of Organic Synthetic Methods, Vol 11
174
Section 74C
Bu ph-
, THF , 6 0 T
5% S I I I ( O ~ - R3) ~h.
I
*
QEt Ph
c-,"'^px"
Shiraishi, H.; Nishitani, T.; Nishihara, T.; Sakaguchi, S.; Ishii, Y. Tetrulzeilron, I 999, 55, 13957. 1. C&I-13C=CB(Oi-Pr)3, toluene, BF3-OEt2 90°C
Ph
t
2. Li+ , II+
ph
63%
97%
Shen, L. Tetrulidron, 1999, 55, 14235.
Brown, C.D.; ;M.. J-
PhS02(CII2)SMe, ??IF BuLi ,PhCOCl, I-BuOK -78°C Orita, A,; Yaruva, .I.;
.-, It
75%
reflux
4
Angew. Cliein. Int. Ed., 1999, 38, 2267.
."<
cat Pd(PPh3), , NEt3 D M F , 80°C. 1 h
c85
65%
,.Isutsui, 11.; JVarasaka. K. Choni.I x t t . , 1999, 45. COzMe
Ti(0i-Pr),/N2/Li TMSCl, C s F , It 'ITIF, 0.8 h
Akashi, M.; Nishida, M.; Mori.
-m:2
Chcvn. Lett., 1999, 465.
H
SECTION 74C: ALKYLATIONS AND ARYLATIONS OF ALKENES
(yBr (FIO)ZB
N
C@Me
4
NlIBoc
*
C S F , DME, cat Pd(PPh3)d 54% 80°C. 3.5 h Collet, S.; Dnnion-Bougot, R.; -)n. D, Synth. Conmun., 2001, 31, 249.
NIIBoc
Section 74C
Alkylation and Arylation of Alkenes
175
A
1. PhMe2SiCu(CN)Li ,THF, -30°C
0
Liepins, V.; Biickvall. J.-E. C ~ C NConznzun., I. 2001, 265.
MqN
MqN
40"C, 15 h
Choi, T.-I..; Chatterjee, A.K.; Gruhhs.
TLtL Angew.
83% (25:l E:Z) Chern. Int. Ed., 2001, 40, 1277.
PhI, Pd(0Ac)z , DMF AgZCO, , 120"C, 3 d PhO2S
5 ) 86%
Maulebn, P.; Alonso, I.; w r o . .1.C.Angew. Chern. Int. Ed., 2001, 40, 1291.
( O-DPPB)O
, tolue11e 1%) [Rh(CO),(~ac)l,SO"C
4% P(OPhh, 02. pyridine , AcOIi 1:l H j C O , 20 hx.5 d (o-DPPB)O 5 1 % (9 1 :1 Jyn:anti)
Ih&.A; Zahn. S.K. Angew. Ch~rn.Int. Ed., 2001, 40,1910. 10%In(OTf), , DCM ,rt
(X0:20 syn:unti)
79% (68:32 E:Z)
Loh. T.-P.;Tan, K.-T.; IIu, Q.-Y. Awgew. Clioni. Int. Ed., 2001, 40, 2921.
176
Compendium of Organic Synthetic Methods, Vol 11
Section 74C
M&II(C02Mekt DCM , 1 d cat Al(Oi-Pr)3 ,reflux
*
&c02Me
90% CO2MC Black, P.J.; IIairis, W.; Wiliams, J.M.J. Angew. Chenr.Int. Ed,,2001, 40, 4475. 1 . S% C ~ c lS%, NaOl-Bu, 0°C
S% S-p-Tol-BINAP , Ph2SiII2
L
P
h
*
L
,,,P#
h
toluene 2.2eqBilBr, 1.2eqTBAF ,rt DCM , toluene, 1 d 67% (94:6 dr)
Yun, J.; Buchwald. S L 01.8.Lett.. 2001,3 , 1129. Sc(OTfh , 0 2 BEt, , DCM/rIIF &
Sihi. M.P.; Chen, J.; Rheault, T.R. Org, k , t t . , 2001, 3, 3679.
63% (20: 1 u n t h y n )
53% (33:l Z E ) Cooper, J.A.:Olivares, C.M.; Sandford. G . J. Orx. Chenr.,2001,66,4887.
2
C02E t
-
4 eq PhMqSiH ,196 H2PtC16 DClE, 23°C , 13 h
Perales, J.B.; van Vranken. D.L. J. Org. Clzenz.,2001, 66,7270,
+02Et SiMezPh
94%
~
177
Alkylation and Arylatiori of Alkeiies
Section 74C
/ FISiMezOSiMe3,DCM , -20°C KWAcOI-IDMF, rt , 2 d OPiv
85% (>50:1dr)
ORv OPiv
J. Org. Cheni., 2001, 66, 7639.
Pei, T.;
OPiv
Bu3SnPh, 5% PdCI,(PhCN), AsPh3, CuI , [hinim] BF,
Ph 66%
ionic liquid medium *
X. Org. Lett.. 2001, 3, 233.
; Zhang,
1 . 5 %C u c l , 5% NaOt-Bu, 0°C S%S-p-Tol-BINAI’, PhzSilIz toIue11e 2 . 2 q B n B r , 1.2 eq TBAF , rt DC?M , toluene, 1 d
*
Ph Yun, .I.;
’
Org. Lett., 2001, 3, 1129
2
Yang, C.; Lee, H.M.;
Br, 120”C, 1 h S.P. 01-8. Lztt., 2U01, 3, 1511. CXI Cs2Ct13
w.
PhB(OII), , ~ O % J P ~ ( O A C3)hZ , 2 y CU(OAC)~ LiOAc , ,DMF
quant
r%
84%
100°C CQBU Du, X.; Suguro, M.; Ilirahayashi, K.; &tori. A; Nishikata, T.; I-Iagiwara, N.; Kawata, K.; Okeda, T.; Wang, 1.I.F.; Fugami, K.; 01%. Lett., 2001, 3, 3313.
178
Coinpendiuin of Organic Synthetic Methods, Vol 11
qMe
Section 74C
OMe
1.5q
SiMezt-Bu t
-
B
u
M
Q
S
s
e
0.6 AIBN , hexane (0.2SM)
EtOzC COzEt Ainrein, S.; Tiiruiierinann, A,;
CQEt
61% (dr=1:1) Org. LAC., 2001, 3, 2357.
0
-
TiCb , E M -78°C It
C02Et
-M ‘~~~ffflflf
55%
Browder, C.C.; Marmsiter, F.P.; west. F a Org. Lett., 2001, 3, 3033.
Bominerijn, S.; Martin, C.G.; Kennedy, A.R.; Lizos, D.; Murnhv~.5.4: Org. Lta., 2001, 3, 3405. SePh
BuSStlII, AIBN hv , 17°C
O% -
+ Ericsson, C.; PhNz + BFd-
GO% 1/45cis/&ms 72% 7.4.1ciskruns
3eqAlEt3
Org. Lett., 2001, 3, 3459. B(0H)z
iinklamliuin salt 2% Pd(0Ac)Z TI-IF ,rt , 3 . 5 h Andrus.; Song, C. Org. Lc,?f., 2001, 3 , 3761.
*
mPh
Ph
83%
Section 74C
Alkylation and Arylation of Alkenes
/
179
1. MeMgBr ,TIIF, -20°C 2. Mg(BiCH,),
95% of cyclized product anthracene ,ultriound THF ,23"C, 8 h 3. T € I F ,reflux , 5 h PhS 4. H,O Cheng, D.; Zhu, S . ; Yu, Z.; &hen. T, J . Am. Clwnt. SIC., 2001, 123, 30.
/ \
C0,Me
, 10.4%KnC13*311,0
2 atino, ,6.1 atin co 180" , 2 d , pressull: tuhe , PhH
-
Weissman, H . ; Song, X.; Milstein. D. J. Ani. Chenz. SOC., 2001, 123, 337.
\
CO2Me
34%
OMe
THF, NMP ,100"C Dai, C.; Fu. G C, J. A m CALWI.SOC., 2001, 123, 2719.
I
82%
t
2. ether, -70°C vacuum -78"C-t
A
Ph
-30°C
56% (2:1) 4. MeOII m e n . T,; Kreethadumrongdat, T.; Liu, X.; Kulkarni, V. J. Ant. Chcm. SOC., 2001, 123, 3478.
PhMgBr cat CoC4(dpps)
vo
?,IF, 0" ,3Om
CSII,,
*
$"
80% (55: 45)
P11
GHll
Wakahayashi, K.; Yorimitsu, 11.; Qshima. K. J. Ant. Clzcm. SOC., 2001, 123, 5374.
Compendium of Organic Synthetic Methods, Vol 11
180
1. scc-BuLi, (-)-sparteine, ether*
N
I
2. ChCN / 2LiCI / TIIF 3. Pll--.n_Ph ,-60°C
B oc
--t
L
P
I
rt
Section 74C
h 90% (>90% ee)
B oc
Dieter., Topping, C.M.; Chandupatla, K.R.; Lu, K. J. Am. Chem. Soc., 2001, 123, 5132.
; .D-
..
* .
q :y
Kumaragurubaran, N.;Sharada, D.S. Tetruhedron LEtt., 2001, 42, 85.
BH
A 01-1
1. Ph2(CHFCH)SiQ , DMAP
2. Pd(PPh,)4, NBt, ,M K N
I
89%
Mayasundari, A.; Young, D.G.J. Tetruherlron LEtt., 2001, 42, 203.
93% (86% ee)
on. S . L ; Fu, Z.; Xie, D. Totruhedron LL’tt., 2001, 42, 365.
PhI,?’HF,‘lBAF,2h
BU
P *B h’ PdClZ(PhCN)z, 50°C Itami, K.; Nokami, T.; Yoshida, .I.-i. .I. Ant. Cheni. Soc., 2001, 123, 5600. 1. 5% RhCl(PPhR), 2. INHCI toluene, 125°C
& 1 I ’
/ Thalji, R.K.; Ahrendt, K.A.; Bergman, R.G.; J. Ant. Cheni. Soc., 20UZ, 123, 9692.
99%
+Q&
/
71%
Section 74C
dc3~,7
Alkylation and Arylation of Alkenes
181
SiPhH, PhSiH3, Sincomplex -C8H17 * I1,PhSi toluene, fi, 3d
.
U Zhang, Y.; Tardif, 0.;
+
5) 95%
(95
J. Am. Clzm. SOC.,2001, 123, 9216.
EtHm
chiral dianune ,THF 2.1
. . F3 C
Slhl.; Asano,
EtMgCl ,-78°C:
Y. J. Am. Clzeni. SOC., 20UI, 12.3, 9708. cat Ti(TADD0L) cornplex
Ph-OH
m2Me
Zn(CH21), MS 4A
c
O Y N H F3C 76% (79%eel
P
h
v
O
I
I
CH2C12,0°C 85% (96:4) Charette, A.B.; Molinaro, C.; Brochu, C. J. Ant. Clicmz. Soc., 2001, 123, 12168.
Bauer, A.; lvfiller. M.W.; Vice, S.F.; McComhie, S.W. Synlett, 200I, 254. Pll
Li
mCHO
Ph
Ph
2. 4 eq BuLi , ether 3. H,O+
-CHO Ph
-
--
BU
78% (94%ee ,S) Br&inond,N.; Mangeney, P.; f\Tormant.J.F. Tetruherlron LEtt., 2001, 42, 1883.
182
&
I
Section 74C
Compendium of Organic Synthetic Methods, Vol 11
==(SiPhzMe F
5% Pd(PPh3)4, DMF 1.5eq KF,25"C 20% CuI ,80 h
+& Ph
60%
o. T.: Kohayashi, T.; Kondo, M. Synlctt, 2001, 281.
M Q C Me
In , TIIF , -78°C 4 eq MeMgCl ,LiCl
*
10% CuC12,O.S h TrOi IzCh Ide, M.; Nakata. M. Synlett, 2001, 1511.
TI00
MgB r
/
EtOzd Dohle, W.; Kopp, F.; Cahiez. G.: Knochel. P. Synlett, 200Z, 1901.
Kitagawa, 0.;Fujiwara, H.;
Tetruherlron Zxtt., 200Z, 42, 2165. acetone, THF
Ph
20% S-l-(2-pyriulidiiylmethyl> pymlidinone
Betancort, J.M.; Sakthivel, K.; Thayumanavan, R.;Barhas III. C .F. Tctruherlron Lett., 2001. 42, 4441.
47% (59% ee)
Section 74C
Alkylation and Arylation of Alkenes
183
HJL1WdTr\.; . ,. . . Okahe, T.; Hakoda, K.; Hoshi, T.; O m , €1.; Kamat, V.P.; Suzuki, T.; Ando, M. Tetruherlron Lxtt., 2001, 42, 2705.
Bu,SnH , BEt, ,PhII 2 m M ,rt
COzMe ;-
. ..
83% (mix ofisomem) Tetruhedron Lttt., 2001, 42, 2157.
Maiti, S.; Katsumata, A.; PhI-I, CF3S0311 , ~t
p
4h
*
Ph
86%
I(lumnn.D.A.; Beauchamp, P.S.; Sanchez Jr., G.V.; Aguirre, S.; de Leon, S. letrulierlron h t t . , 2001, 42, 5821. AcO
-\Qc4r"
AcO
2
PhCH=CHZ , DCE, 2 d
Gruhhd catalyst, it , 0.15 M
OAc Forget-Champagne, D.; Mondon, M.; Fonteneau, N.; Gesson. 1.-P. Tetmlterlron Lxtt., 2001, 42, 7229.
Lapinsky, D.J.; Beremeier. S.C Tetrulierlron Lett., 2001, 42, 8583 .&
OAc
75%
184
Compendium of Organic Synthetic Methods, Vol 11
1 . LiH 2. MeLi/C&IJ72
Section 74C
h
3. dilute HCI M PhL Bartoli, G.; I2i&ozzo. &; De Nino, A.; Procopio, A,; Sambri, L.; Tagarelli, A. Tetrahedron Lett., 2001, 42. 8833.
e
94%
Cp2ZIc'Iz , DMF, 130"C, 6 h
*phq
PhBr ,cat Pd(0Ach , PPh, Cs2CO3
I&~cL& Heiennann, J.; Mlura,;Inoh, J.4; Pivsa-Art, Cheni. Eur. J., 2000, 6, 3426.
A
MgCl
PI1
Ph
p
h
Ph
7% :
*I S.; Satoh, T.; Nornura,
M.
, NiCb ,ether, 12 h
chird phosphino-quinocorine
65% (75% ee)
Ph PeIlet-Rostaing, S.;Saluzi?o, C.; IIalle, R.T.; Breuzard, J.; Vial, L.; 1-e Guyader, F.; Tetruhedron Asyrii~ri.,2001, 12, 1983. # - y e l i g 2
Ot-Bu
C3H7
Ferreira, F.;
I.
IJ
* M%Si
3 eq ZnBrz, 20°C 2.1120
Eur: J . Oi-8. Cheni., 2000, 3581.
78% ( 9 5 5 E:Z) (73:27 syn:unti)
Of-Bu
Section 74C
4
Ph
Alkylation and Arylation of Alkenes
1. L i , S% DTBB , 3 eq MqSiCl 'I'IIF, -78°C 4 0°C
185
SiMe, .r
L
s
M
e
70%
3
2. HzO
Ph yus. M.; Martinez, P.; Guijairo, D. Tetruhedrnn, 2001, 57, 10119.
2,.
Ph21+ BF4-, 5% P ~ ( O A C ) ~
2.5 eq N a g 4 , TEBA DMF. 6 O C , 6 h Ph Z.C Synth. Comniiin., 2000, 30, 1281. Xia, M.; k.
*
81% Ph
PhSiMt=,O€I,a t P ~ ( O A C,) 1~d
B ozcu-\
Cu(OAc)2 , LDAc , DMF, 100°C
-
ph*C&Bu
78% Hirahayashi, K.; Ando, J.-i.; Kawashinia, J.; Nishihara, Y.; Mon.;Hiyama, T. Bull. Chmi. SOC. Jpn, 2000, 73, 1400. PhOTF , chiral Pd catalyst i-PrZNEt, T I I F , SOT , 2 d
-
87% (85% ee)
QPh
B~,sIIH, PtlrI
AIBN , 80°C
*
L
S
M
4-
Z S
17%
Della. E.W.; Graney, S.D. Teti-ulzerlronLett., 2000, 41, 7987.
70%
PhBr , NaOAc , TBAB
* Ph-COzBn 1% Pd-henzothiamlea r l x m e complex, 130"C, 4 h Calb. V.; Nacci, A,; Lopez, L.; Mannurini, N. Tctruhedron Lett., 2000, 41, 8973.
w;Kamesh, C. Tetruhcrlrnn Lett., 2000, 41, 8981.
0 13%
90%
Section 74C
Coinpendiuin of Organic Synthetic Methods, Vol 11
186
73%
M.-7.. Trtruherlron Lttt., 2000, 41, 90x3.
Yao, M.-L.;
Bod IN
Y
S i(OEt),
Si(OEt),
Rhz(OAc), toluene, reflux C3H7 Tttruhcdron Lett., 2000, 41, 10175.
B 1 ' c ' 1 N ~ c 3 H 7
-
IIewitt, G.W.; Somers, J.J.;
61%
82%
C.-H. J. Org. Chent., 2000, 65, 1767.
Chang, €1.-M.;
YBJ
PhBfOH), ,Na2CO3 ,XO"C
N
C ~tI Pd(PPh3)4
I TS
, THF-HZO
Me
,TBAF,rt
1% Pd(dba)z, TIIF
I
J k i i n a r k . S.E.; Wmg, 2. Syntlwis, 2000, 999.
C=,H I
B(0H)2
, THF
Pd(M&N)zC12, AsPh3, AgO 70°C
Yao, M.-L.;
I
5
%
Or$. Lett., 2000, 2, 1213.
0'-
CO2Et
pN :
Ts
*.
Lee, C.-W.; Oh, K.S.;
K
J. Org. Clwii., 20U0, 65, 5034.
IIZCkHC
CO2Et
93%
Section 74C
Alkylation and Arylation of Alkenes
h
Br/n/
Ph , dioxane , 8 0 " ~
3% Pd(PPh3)4, 1.5 eq Ag20 ~ ( 0 1 1 ) ~3.3 eq NaOH (3N)
Zhou, S.-in.;
187
-4 80%
Tctruh~&on Lc.tt., 2000, 41, 3951.
pb
Ei Norskian, S.;Baudry, M.; .-
98% J.F. Tctruhedron Lett., 2000, 41, 6575. Ph
I
di( 1- adanantyl) n-butylphosphine 98% Ehrentraut, A,; Zapf, A,;
b
Synlert, 2000, 1577.
1. 1.1 eq BF3.OEt2 2 eq Et3Sil-I 2 . 1 N HCl
Giese, S.; West. F.G, Tetruhedrnn, 2000, 56, 10221
71%
14%
Section 74C
Compendium of Organic Synthetic Methods, Vol 11
188
0.2 Sc(OTf), , [einim] ShF6 PhII ,20"C,12 h
a:) C3H7
d7 *T
lemim] = 1-ethyl-3-methylimidmlium (1 3 : 1) 96% (an ionic liquid) Sent...; Shim, W.H.; Roh, E.J.; Choi, J.H. Cherri. Conurzun.,2000, 1695.
Yorimitsu, H.; Shinokuho, 11.;
aq H 3 P 0 2 , NaIIC03, AIBN
EtOH ,reflux, 5 h
*
Chcm Lett., 2000, 104
m;N/t-Bu
,PI'
[Pd(OAc),/LiCl]
Ph
Diederen, J. J.H.; Sinkeldam, R.W.; Frirhauf. H. -W.; IIiemstra, H.; Vrieze, K. Tetruherlron Lxtt.. 1999, 40, 4255.
CSHI 1
1 . i-Pi0,CCI , Et3Al-JJ3 DCM ,-15°C rt
TBrTBr
m
Biermann, U.;
C
5
H
lI
--+
*
L C 5 H l , C5f111
2. HzO
w.J.O. Angew. Chern. Int. Ed., 1999, 38,3675. , a
67%
PhZnBrTHF,rt , 5 % Pd(PPh,),
Br Villiers, P.; Vicart,
Ph
N.;Rarnondenc, Y.;PIC. G. Tetruhedr-onL t t . , 1999,40, 8781.
Section 74C
Alkylation and kylation of Alkenes
JPh +
-
r
NMP,Pd,(dba)3*CHCl3 I
(Et0)3SiH, KOAc
189
/ph
(EtOhSi
(EtOhSi
(97 : 3) 81% Tetruherlrnn k , t t . , 1999, 40,9255.
Murata, M.; Watanahe, S.; OB n
0Ac
2. H2 , Pd-C , EtOH 3. A c 2 0 , NEt3 , DMAP
J. h
Ishihara, K.; Nakamura, S.;
i .
40%overall (44% ee) Cliern. Soc., 1999, 121, 4906.
PhI, 5% Pd(dhah, THF
mSi,
C5HI 1
Me
*
3 ey Bu4NF, 10 inin
Denmark. S.E.; Choi, J.Y. J. Am. Chpnz. SOC.,1999, 121, 5x21.
CSHll* ph
91% (En,99.910.1)
PhI, cat Pd(PPh3)&~1
SIIBU~
THF ,reflux , 1 h
Chen.;Wilcoxen, K.; Zhu, Y.-F.; Kim, K.-i.; J. Org. Chem., 1999, 64,3476. P h-I Kamatani, A,;
86%
I
,976 PdClz(dppf) 4NJichz
*
wNHC
Ph
'ITIF, rt , 1 h J. Org. Clwii., 1999, 64,8743.
Ph
86%
Section 74D
Coinpeiidium of Organic Synthetic Mcthods, Vol 11
190
Bu
OMe #
P oH h-
2. BuLi ,(-)-S-sparteine -SO"C, cumne 3. HzO 4. MeOII, 3N HC1
Norsikian, S.; Marek.
L;Poisson,
i i
P O h-H
72% (95% ee) J.-F.; Norm ant. J.F. J. Org. Chem., 1999, 64, 4898.
OTBDPS
5% Pd(PPh,), , T H F
PhI, S% PdClz(MeCN)z, DMF
B u,Sn
2S"C, 12 h
Rousset, S.; Aharhri, M.; Thihonnet, J.;
Pb,
. . . nuchene.,
H'c=c=q
c0,pe I
H Me
NaH ,5% Pd(dba)2 10% PPh,, NE t3 T H F , reflux , 18 h
Kato, F.; Hiratsuka, Y.; Mitsui, T.; Watanahe, T.; HiuiJ.
SECTION 74D:
Ph Org. Lett., 1999, 1, 701.
-
61% (50% ee) Ph Heterocycles, 1999, 50, 83.
CONJUGATE REDUCTION OF a$-UNSATURATED CARBONYL COMPOUNDS AND NITRILES ASYMMETRIC REDUCTIONS
uoH
S 96 [R h(cod)(f erioce ne derivative )] B F4
Ph
Tan&,
Hz , THF , 100°C
K.; Fu. G.C, J. Org. C ~ P I2001, ~ . , 66, 8177.
* L Ph
C
H
O
91% (75% ee)
Section 74D
Conjugate Reductions
191
Aco2H -Aco2 H2- , Ru(O2CMe)z pol-BINAP))
[hinim]PF6,H 2 0
quant (92% ee) Brown, R.A.; Pollet, P.; McKoon, E.; Eckert, C.A.; Liotta, C.L.; b o p . P.G, J . Am. Chern. Soc., 2001, 123, 1254.
Br
A
Bn02CHN
C02l3
* Et02C
Z n X u , DCM ,~t
I Li, W.; Zhnng, Z.; Xiao, D.; a
J
82% (28:72 antisyn)
. Org. Chern., 2UU0, 65, 3489.
2 Y
reductau: D74 fiuin Nicotiuna tuhucimi NADPH , Triton-X-l00,35"C, 8 h Tiis-HC1 buffer , dithioeiythivitol HOCH,CI12SH
Hirata. T.; Shimoda, K.; Gondai, T. Clzerrz. Lm,2000, 850.
99% (97% ee ,S)
6
NON-ASYMMETRIC REDUCTIONS 2%J ~r(cod)CI],,I-PiOII , toluene 2% dppp, 2% C ~ 2 C 0 3,8O"C, 4 h
*
98%
Sakaguchi, S . ; Yamaga, T.; Lshii. Y.J. Org. Chem., 2001, 66, 4710. 1. BuLi, TIIF, -30°C 2. CUI
4. 2N I1C1 Peron, G.; Norton, D.; Kitteringham, J.;
iid,
Tetruhedron Lttt., 2001, 42, 347.
1. CdI12 , AlC13 , DCM
2.H20 Shirini, F.; Zolfigol, M.A.; Azadhar, M.R. Russ. J. Org. Clzcm., 2001, 37, 1600.
65%
192
Section 74D
Compendium of Organic Synthetic Methods, Vol 1 1
C0,Ph
C02Ph
Cornins.;Brooks, C.A.; Ingalls, C.L. J. Org. Chent., 2001, 66, 2181.
*
[MgBr] [Bu,S I&-I- HI+
C 0 2 Bn
THF, rt
Shibata, I.; Suwa, T.; Ryu, K.; MeO,
A
Ph s c o 2 B n
*
m~a.A . J. Org. Cl~enr..2001, 66, 8690.
[Rh(ligaid)(nhd)] BF4, H 2 , I’HF N I IAc
*
2h
90%
P
1
- -
mI
98.7% ee Yasutake, M.; Gridnev. I.D.; Iligashi, N.; Iinamoto. T. Org. Letf.,2001, 3, 1701.
m:
In , EtOH ,NH,CI, H I 0 * 90°C , 9 h
85%
Dutta, J.; Guchhait, S.K. Org. Lett., 2001, 3, 2603.
Ph
CO*H
1.2.5MaqNaOH, 16h cat PdCl; , HCOOII, 65°C
* Ph 2. 2M HCI ,4rterhurn. J.B.; P a n d a , M.; Gonzilez, A.M.; Chamberlin, R.M. Tetruhcdrnn L.dt., 2000, 41, 7847.
‘OzH
98%
Br3SnH , AcBr PhII, A Behbington, D.; Bentley, .I.; Nilsson, P A . ; Parsons. A.F. Tetrahedron Lett., 2000, 41, 8941.
Section 74D
193
50%
--
A
A
.
.,
Conjugate Reductions
Waring, M.J.; Scott, D.A. TetuhacIron Lett., 2000, 41, 9731.
6
3% ( ) - R h catalyst
CO2Me
Ph
N I I C O ~ M ~15 psi H2. TIIT;,6 h
C02Me
* A ph
NHCO2Me
Taylor, R.A.; Santora, B.P.; Q e n C . M .K.Org. LEtt., 2UU0, 2, 17x1.
A
Ni(R) , EtOAc , rt , 2 5 inin ultrxound
Ph
Ph Wang, 11.; Lian, H.; Chen, .I.Pan, ; Y.;
Ikeno, T.; Kixnura, T.; Ohtsuka, Y.;
93%
LP
* Ph
95%
Synth. Comniim., 1999, 23, 129.
.
Synfett, 1999, 96.
Ni(R) , THF , rt 20 mill
qW% -a
111111111
* >
0 Barrero. A.F.; Alvarez-Manzaneda, E.J.; Chahhoun, R.; Meneses, R. Synfe??,2999, 1663.
2
Ph
Mori.;Fujita,
[PhMqSaI/O.5 CuF(PPh3&*2EtOH DMA,O"C-+ i t , 2 h
Ph
92%
A.; Kajiro, 1-1.; Nishihara, Y.; IIiyaxna, T. Terruhedron, 1999, 55, 4573.
194
Compendium of Organic Synthetic Methods, Vol 11
Section 74E
SECTION 74E: CONJUGATE ALKYLATIONS
BII-
5
ASYMMETRIC ALKYLATIONS
N
dioxane ,R-BINAP ,40°C cat Rh(acac)(%H4), , 12 h
0 74% (96% ee)
Bn Senda, T.; Ogasawma, M.; flilyashi. T. J. Org. Clwiii., 2001, 66, 6852.
- mNH YNB2 2 eq PhB(OH)2, aq dioxme 0.5 K2CQ , lOO"C, 16 h
0
ph
3% Rh'(acac)(C2H&
6
62% (89% ee).
Sakuma, S.; Mivaura. N . J. Org. Chem., 2001, 66,8944.
1
betz.
0
P h-B (OH quant (97.5:2.5 S:R)
3% Rh(acac)(C2II4)2 L* * dioxane , 100" , H 2 0 , 5 h
Ph Moulin, D.; Gosherg, A. Org. LL'tt., 2001, 3, 4083.
0 N
I Me
cat chiral imidazolium salt
THF-H20 , 4 0 " C , 27 h
Me
Me
83% (91% ee)
Paras, N.A.; MacMillan. D.W.C. J. Am. Client. SOC., 2001, 123, 4370. M Q C I I N O ~ NaOf-Bu , azacmwn ether-phosphine oxide Ph-
Ph
toluene
* 02Ph %,. 43% (95% e e , R ) Novik, T.; Tatai, J.; Bak6.;Czugler, M.; Feglevich, G.; Tcke, L. Synleff, 2001, 424.
195
Conjugate Alkylations
Section 74E
PhB(OH), , aq dioxane 1%Rh(acacXC,I14)z chiral phosphine , 100"C, 1 h * ph&o
99% (96% ee) Tetmheilron Lett., 200Z, 42, 921.
Kuriyama, M.;
Et,Zn , 2% Cu(OTf), , bluene 4% phosphorainidite ligand -2O"C, 1.5 h
-%
(98% e e ,R) Et
March, ; S.; Cuillen, F.; Benhiihn, C. Alexakis, A,; Rosset, S.; Allamand, .I. Synlett, 2001, 1375.
/CC12Me ,20% t-BuOK Ph-CO,Me
10% TPODAL oxazr)lines toluene, -78°C
COzMe
* PhL
a
z
e
80% (56% ee)
Tetmherlmn Lc.tt., 2001, 42, 4175.
Kim, S.-C.;
CHz(CO2Et)z, t-BuOK, 20°C phase transfercatalyst , toluene PhL
M
P
h
CII( COzEth Ph
Ph 74% (35% ee)
D.Y.; Huh, S.C.; Kim, S.M. Tetruhecirnn Lett., 200Z, 42, 6299. 10% Ph
Ph
&OH
TKT-N
Ph
9% Ni(acach , 2.2 MtC N
E t 2 '-30"z h
PhJJPh 7.5% (78% ee ,R )
Shadakshari, LJ.; Navak. S.K. Ti,truhedrrin, 2001, 57, XIX.5.
/+
COzf:t
1. O.S%,CU(OT~)~ , Et&n l%TADIX>L ligand
toluene , - S T , 3 h * ka2Et 2. 2N IICl mA., , . Benhaim, C . Tetruhetlrnn A s Y ~ ~ w 200Z, I., 12, 1151.
cn, Et
COzEt quant (20%ee)
Coinpendium of Organic Synthetic Methods, Vol 11
196
..._ri)
Section 74E
Et,Zn , 0 . 5 % CuI , E M , 10 h
c c
1% quinoline-phosphine ligand 0.25 Zn(OH)z, -20°C
Delapierre, G . ;Brunel, J.M.; Constantieux, T.; Terruhedron Asynint., 2001, 12, 1345.
"%//
Et
quant (53% ee)
>
Et,Zn, toluene, -35"C, 3 h 1.2%Cu(OTf),
1.3%~ c h i d phosphoramidate ligand
Mandoli, A,; Arnold. L.A.; de Vries, A.H .M.; Tetruhedr-on A .synini., 2001, 12, 1929.
Et,Zn , toluene , -20°C
89%ee,R
-8.
4% c h i d diunine-carhene ligand
%/,
Et 92% (22% ee, S) Guillen, F.; Winn, C.L.; Alexakis. A. Tetruherlron Asymni., 2001, 12, 2083. 4% Cu(OTf), , 2 h
R
0
Et,Zn , toluene , 0°C 2% silver diamino-cailwne 2% Cu(OTf),
a
98% (23% ee) Pytkowicz, H.; Roland. S.; Mangeney, P. Tetruhorlmn Asymm., 2001, 12, 2087.
PI1
Tong, P.-E.; Li, P.;
Ph
&.
EtJn , chiial unino-alcohol MtCN, -3o"C, 12 h
* Phu
p
h
89% (82% ee, S) A S'.C'. Tctrul7erlron Asyrizni., 2001, 12, 2301.
Section 74E
Conjugate Alkylations
197
c
Jha, S.C.; Joshi. N.N. Tetruhcrlmn A s y i i m . , 2001, 12, 2463
Et,Zn , 2% Cu(OTf), , 16 h 4%phosphonite ligiuid toluene, -30°C
quant (41% ee ,R )
% " ,,
Et Tetrulicdmn Asyinnz., 2001, 12, 2497.
;-
1,
. T
Ruiz, A,; Claver, C. Teti-uhcrlron Asyinni., 2001, 12, 2861.
15%L-prOli~e NO2
x e tone, DMSO, rt
NO2
h s t . B.; Pojarliev, P.; Martin, 11.1. Oq. Lett., 2001, 3, 2423.
97% (7% ee)
his-oxawline ligandKh(OT1h 1-1 PI1
Zhuang, W.; Hansen, T.;
Id Chciii. Coiiiimin.,
73% (60% ee) 2001, 347.
Coinpendiuin of Organic Synthetic Methods, Vol 11
198
Section 74E
MeOzC 1.3 Mg(C10,)z ,EtI l 0 q Bu3SnH, DCE
)-.”’
- Hbo
BEt3,Oz. his-oxamline -78”C, 3 h (2- naph th)
(2-naphth)
79% (84% ee) Angew. Chein. Int. Ed., 2001, 40, 1298.
Nukamura, I.; Oh, B.H.; Saito, S.;
, 0.15 AgOTf, H20
C02Bn
0.1 R-Tol-BINAP ,0°C 94% (56% ee) Kohavashi. S , ; Kakumoto, K.; Mori, Y.; Manahe, K. Isr. J. Chein., 2001, 41, 247.
0
. DCM, 10h chiral Ru complex , KOH
/-l-
Suzukl.;Torii, T. Tc.truhedrrin A.syiriin., 2001, 12, 1077. Et,Zn, Cu(0Tf)Z , DCM chiral xylofuraciose ligand 92% (60% ee) rt,lh
Et
P\am.les.,Net, G.; Kuiz.;Claver, C.; Woodward, S. Tetruhadron Asyrnm., 2000, 11, 871. Cu(OTf)2-chiral phosphite oinplex Et2Zn, toluene, 0°C , * 3h Yan, M.; Zhou, Z.-Y.;
tL
Llhan. A.S.C. Ckiiz. Cnnrrizrm., 2000,
115.
quant (73% ee)
e
199
Conjugale Alkylations
Section 74E
94% (64% ee)
Tomioka.; Nakagawa, Y. Hcterocyles, 2000, 52, 9s. Et2Zn, Cu(OTQ2 , blueiie chiral quinoline binaphthol ligand -15"C, S h
4?A Ph
Et :. Tetruhedron Asymm., 2000, 11, 2387.
dolle,I-
Arena, C.G.; CXahrb, G.P.; Francib, G.; F;rr
Ph
(i
96% (70% ee)
-WC Et2zn, 2 . m cU(o'rq2, 5% chiral phosphomnidite toluene
*Phu
p
Arnold, L A ; Zlnlios, R.; Mandoli, A.; de Vries, A.H.M.; Naasz, R.; m Tetruhedron, 2000, 56, 2865.
Et,Zn , 3 % Cu(O'TQ, , toluene, 15 h cat c h i d oxmline-phosphik ,-20°C
c
*
Escher, 1.1-1.;&lkA Tetruliedron, 2000, 56, 2879.
h
85% )89% ee) a . B.I..
bEt
99% (up to 86% ee)
2 HI EtllZn , chiral QIJII'IIOS catalyst 0.5%CUI , DCM , 1 1 2 0 ,-20°C
Delapiene, G.; Constantieux, T.; Brunel, J.M.; Buono.
76% (61% ee) Et
Compendium of Organic Synthetic Methods, Vol 11
200
Section 74E
CH2(C02Bn)z, 0°C ,45 h
53% (85% ee)
La-linked-BINOL coinplex
C H(CO2Bn)2
a
Kim, Y.S.; Matsunaga, S.; Das, J.; Sekine, A.; J. Am. Chenl. SOC., 2000, 122, 6506.
Ph
Et,Zn , MeCN ,-30°C Ni(a c a ~ ) ~
Ph
chiral thioether alcohol catalyst
Phu
p
h
94% (60% ee) Yin, Y.; Li, X . ; Lee, D.-S.;Yanc. T.-K. Tetruherlmn Asynln~.,2000, 11, 3329.
Schneider.;Reese, 0 . Synthesis,
PhBs
2000, 1689.
1. BuLi 2. B ( 0 M e h 3.
n (
Takaya, Y.; Ogasawasa, M.; Hayashi, T. Tctrulicrlron Lett., 1999, 40,6957.
4
-Ai
1. cat. Ni(acach(chisal oxuolidine) M q Z n , TMSCl , tiiglyine
ECsCEt
2. H?O+
78% (81% eel Beds. S.-i.; C h i , D.-M.; Sato, Y. J. A I I LChw1. Snc., 1999, 121, 4712.
Et
Et
Section 74E
Conjugate Alkylatioris
EtzZn, 1 % Cu(0Tfh
201
?L
quant (90% ee ,S)
2% chiral aryl diphosphite tolucrie ,0°C , 1 h
S . C . Tetrulicdron Lett., IYYY, 40, 6645. S @-Tol)BINAP, 5% CUCl
COzEt
Ph
COzEt
10% NaOt-Bu, rt , 1 d pol yinethyl hydroiloxarie
84% (90%ee)
Applla, D.H.; Moritani, Y.; Shitani, R.; Ferreira, E M . ; B u c h w u J. Aiii. Clieiii. Soc., IYYY, 121, 9473. 0
PhB(0Hb , 3 % Rh/S-BINAP water , dioxane , 100°C
II
94% (96% ee, S)
OEt
IIaYdhhl..; . ,. Senda, T.; Tukaya, Y.; Ogasawara, M. J . Ani. Cliern. Soc., 1999, 121, 11591. Et,Zn, 1% Cu(OTf), , 0°C 2% chiral aryl diphosphi te quant (90% ee)
toluene, 3 h
Et
Yan, M.; Yang, L.-W.; Wong, K.-Y.;
Li[PhB(OMe)J CQMc
q dioxane , 3 h
3% R h(ac ac &I
-tie
, 100°C
i&S-B INA P
Takayn, Y.; Senda, T.; Kurushima, H.; Ogasawara, M.; Havashi. T, Tetruhedron Asyniiii., I Y Y Y , 10, 4047.
Hu, X.; Chen, H.;Z h a n l . . r i g c , w .
Cheiii. b i t .
C02Me
Ed., l Y Y Y , 38, 3518.
>99% (89% ee)
'gMe2 $
Section 74E
Compendium of Organic Synthetic Methods, Vol 11
202
chird R u complex ,DCM , KO13 ,10h
u; Torii, T. Tetrulicdron
suzu
s '
\ Asyiirrii.,
>99% (75% m ,S)
2001, 12, 1077.
NON-ASYMMETRIC ALKYLATIONS
COlEt
Tateiwa, J.-i.;
CqMe
a
,140"C,6h
-k COzEt
0
96%
Eur. J. Org. Chcwi., 2001, 1445.
97%
IIuang, T.-S.; Li, C.-J. Chcwi. Conrrnun., 2001, 2348.
--?
COzMe a t Cu(OTf)(his-oxamline), DCM , -78"C, 2 h
pfi
Jensen, K.BV.; Thorhauge, 1.; Hazell, R.G.; Angew. Chani. Irrt. Eli., 2001, 40, 160.
quant (88%)
Section 74E
Conjugate AIkyIations
0.1%[RhCl(cod)]2 , 9 0 T
1
203
P-TOl
I120
TolB (0H)z , 6 h Cheni. k t t . , 2001, 722. PhSIlMq ,H20,5O"C, 12 h
-Co2Et
COzEt
5% [Rh2(&)2~21
65%
Venkatraman, S . ; Meng, Y.; J .i. C.-L Tctruhedron Lc.tt., 2001, 42, 4459.
&SiM%
0.1 ItlC13
5 eq TMSCl , DCM
':?@
Lee. P.& Lee, K.; Sung, S.-y.; Chang, S. J . Org. Cheni., 2001, 66, 8646.
PhSnMq , 2h
ca t [ Cl(c<)d)Rh]2 I I 2 0 , ulaasoulld 0
Ph
82%
Iluang, T.-S.; JJ.C.-J. Org. Left., 2001, 3, 2037.
0 Ramnauth, J.; Poulin, 0.;Bratovanov, S.S.; Rakhit, S.; Maddaford. S.P. Org. I.&., 2001, 3, 2571.
Betancort, J.M.; Bnlhus IIT. CE. Or
0
87% (85: 15 syn:anti) 69%ee
204
Section 74E
Compendium of Organic Synthetic Methods, Vol 11
1. 2.2 q r-BuLi 2.5 eq HMPA
4 qTMSCl -78”Cd 2. HZO
-
91%
It
Piers.; IIarrison, C.L.; Zetina-Rocha, C. 01-g. Lett., 2001, 3, 3245.
92% (97:3 anti:syn)
Song, Y.; Okamoto, S.; Sato. F. Org. Lett., 2001. 3 , 3543. C0,Me
SnBr3
Ph
AcBr 80°C , PhH
* P
*+ h
40%
k SnBq
Miura, K.; Saito, H.; Fujisawa, N.; Wang, D.; Nishikori, H.; Org. Lett., 2001, 3 , 4055.
+
=<~$-Bu , BF3.OEt2
0
THF , -78°C
+
0°C
t-13uPhzSi
88% Barhro, A.; Castrefio, P.; Garcia, C.; pulido. F.J. J. Org. C ~ C I I2001, L , 66, 7723. A\COZEt
Ph;Bi, air, HzO--TIIF, 12 h
COzEt
S%J Rh2(~0d)zC1,,50°C
80%
Venkatraman, S.; L,i, C.-J. Tetruhedron Lett., 2001, 42, 781. PhPbMe, , air, 70°C a t R h 2 ( ~ ~ d ) 2 C lH2O z,
MeOzC*COzMe
MeOz
15 h Ding, R.; Chen, Y.-J.; Wane. D.: Li. C.-J. Synlctt, 2001, 1470.
85% COzMe
205
Conjugate Alkylations
Section 74E
U'
CH2Cl2,-20°C , 15 min 2. PhCH(OMe),
"",,e
Alexakis.,Trevitt, G.P.; Bernardinelli, G. J . Am.
Et 62% CIwni. Soc., 2001, 123, 4358. 0
II
0
&I
CuI , ether, 0°C
:;rgBr,
-4
58% (1:1.6cis:trum)
Me
Sha.;T s ~ I C.-T.; I ~ , Chang, W . S . Tetrulwdron ILtt., 2001, 42, 683
(BuSe>Cu(CN)BuLi2
TIII', -78°C
>b 96%
Bu
-
>.
Zinn, F.K.; Kamos, E.C.; Comasseto, J.V. Tetrulzedl-on Lcjtt., 2001, 42, 2415.
0
COZEt , h v
CO$t
benzophenone, 2.5 h
70% (1.33:1 E:Z)
W.& IIannan, J.J. Tetruherirnn k t t . , 2001, 42, 3211.
Bu,N Ph3Sir;? , TI-IF
c02et
*Co2Et MS ,7S"C
Xuan, J.X.; F&yJ-L
Tetruherlrnn Lett., 2001, 42, 3275.
c02et
74% (7:l E:Z)
206
Compendium of Organic Synthetic Methods, Vol 11
TBAB , HCOzNa , PhBr , 130°C
C02Me
Ph%
Section 74E
LP
cat Pd-hithiazole coxnplex , NaHC03* ph
Calb. V.; Nncci, A.; Lopez, I.,.; Napola, A. Tetrcrhedron Lett., 2001, 42, 4701.
T
O
L
Pastor, I.M.; LuJyf..
i
1.
D
77%
o ,TI-IF
2 eq CuI , HMPA -78°C 2. NH4Cl Tetruheclron, 2001, 57, 2311.
(95 Giuseppone, N.; C o l l l n . T e t r u k d r o n , 2001, 57, 8989.
70%
5) quant
J(.InC13 DCM, r t , 3 h
ir
*o
H ._ Yadav. J.S.; Ahraham, S.; Reddy, B.V.S.; Sahitha, G. Synthesis, 2001, 2165.
+
Ph
C
N H , f r 2 0 , 21nin
Ph
micmw aves
PhU p : % m g h a d d a m . F.M.; Mohammadi, M.; IIosseinnia, A. Syntlt. Comrnun., 2000, 30, 643.
Section 74E
207
Conjugate Alkylations
CH2(C0,Bn), , THF , 0"
53%
45 h , polymer-hound
La-BINOL catalyst
Matsunaga, S.; Ohshhna, T.;
'
C02Br Tetrulmlron Lett.. 2000, 41, 8473.
0 Bennahi, S.; Narkunan, K.; Rousset, L.; Bouchu, D.; Ciufolini. M .4 . Tetruh~~ilrori k j t t . , 2000, 41,8873.
0
Et,Zn , l%Ca(OTf), 2.5% aminoethyl[ hosphiiies DCM , 0°C , 5 h
Morimoto. T.; Yamaguchi, Y.; Suzuki, M.; Saitoh, A. Tctrulterlron Lett., 2000, 41, 10025.
I
ZnEt, , 2 . 5 eq CuCN, 0°C
99%
NH(Bn)SO#h, toluene, 1 h
Kitdmurd.; . . Miki, T.; Nakano, K.;
Et B i d . Chenz. SOC. Jpn., 2000, 73, 999.
, d ,DMWPy
0.13 CoBrz + 0.26 hpy , 70°C-
E 0,C
Gomes, P.;
; Ntidtilec, J.-Y.; PCrichon,
64%
J. Tetrulieclron Lxtt., 2000, 41, 3385.
Section 74E
Compendium of Organic Synthetic Methods, Vol 11
208
Ph4Sn, cat PdC12,2 eq LiCl
Ph
AcOH , air, 25"C, 20 h
0
81%
Ohe, T.; Wakita,T.; Motofusa, S.-i.; Cho, C.S.; Ohe, K.; 1Jemura. S, Bull. Cheni. SOC. Jpn., 2000, 73, 2149.
@
,DMF
1.
do
0
Ac
Pd(OAc)z, KOAc
c
2. H2 , 5 % P d K , EtOAc
0
64~95% 0 Arcadi. A.; Chiarini, M.; Marinelli, F.; Berente, Z.; Kollhr, L. Org. Lett., 2000, 2, 69.
2
PhI, Pd(OAc)z, NEt3 , X0"C 100 bar COz (supeiu3ical)
*
, Ph .
88% Ph
CJtchl.;Fabrizi, G.; Gaspairini, F.; Pace, P.; Villaui, C. Synletr, 2000, 650.
0 1
2. CH,=CIICO~M~ 150 W lamp, 10°C
Ollivier, C.;
*
Ph
'es-
1. catwhohora1e ,Cat Me2NCOMe
NO2
N- OCOzMe
70%
Angew. Cliern. Int. E d , 2000, 39, 925. Et,Zn, 0.5 Cu(OTf), ,-30°C 1% c h i d P ligand , toluene
Bexakis. A,; Benhaim, C. Org. Lett., 2000, 2 , 2579.
Illraa.;Takada, 'I'. Sakurai, ; 11. Org. Ixtt., 2000, 2, 3659.
*
L
Ph
N
0
2
quait (64% ee)
Section 74E
MeO2C
Conjugate Alkylations
209
PhB(0Hh , aq MeOII ,25"C
-C02Me
4% [Rh(codXMeCNX]BF~, 6 h
Sakuma, S.;Sakai, M.; Itooka, R.; M
a J.
COzMe
M~O~C 84%
Org. Chem., 2000, 65, 5951.
syringe pump (14 h) COZEt
49%
U;Kim, S.K.; Kim, J.Y.; Lim, J . Tetr-uhedmn Letf., 2000, 41, 5915.
3%
58% (1:99 ~ n t i : ~ y n )
IIayen, A.; Koch, K.; Metzeer,.Arigov. Clicm h i t . Ed., 2000, 39, 2758. PhCIIzBr, 2.1 4 CrCI,
*
Mn , THF , 4 . 2 eq 4-t-Bu-piperidine ,4u&.
L; Gil, R.; Kalsey, S. Tetruli~ilronLett.,
ZYYY, 40, 67.
- _.
Phc-N 85%
Kumar.;Keddy, B.V.S.; Keddy, P.T.; Yadav, J.S. Tctruherlron k , t t . , ZYYY,
a
40, 5387.
1. o ( ' : ,B 10% MezNCOMe r l 0 DCM , heat, 3 h 2 . 3 q I I 2 0 ,DMP'CJ , DCM ,Oz
Ollivier, C.;
' Cherri. Eiir. J.,
I Y Y Y , 5, 1468.
86%
Compendium of Organic Synthetic Methods, Vol 11
210
Section 74E
0
da Silva, F.M.; Comes, A.K.; Jones Jr. J. Cun. J. Cheiii., 1999, 77, 624. Bu,GaLi ,TIIF, 0°C + rt
Ph?ph Han, Y.;
*
0 1.
phnphBu
Y . - Z ,Fang, L.; Tao. W.-T. Syntlz. Commun., 1999, 2Y, 867.
EtzNTMS ,50"C, 16h
I
CHO ; Ono, H.; Kornatsuhara, N.; Hoshi, T.; Suzuki, T.; Ando, M. Tetruhedron Lett., 1999, 40, 6627.
C02Et
78%
0
51%
5.5% bis-oxamline , 5 % Mg(0Tf)Z 6% NMM ,CHC13, MS , tt p,,+
CO2Et
JiJ; Barnes, D.M.LZhang, J.; King,
95%
S.A.; Wittenherger, S.J.; Morton, H.E.
J. Ant. Chern. Snc., l Y Y 9 , 121, 10215.
Bosco, M.; Bellucci, M.C.; Marcantoni, E.; Sambri, L.; Torregiani, E. Eur. .I. Or%. Client., 19Y9, 617.
;-
REVIEWS: "Catalysis of the Michael Reaction and the Vinylogous Michael Reaction by Femc Chloride Iiexahydrate," Christoffers. J. Synlett, 2001, 723.
Section 74F
21 1
Cyclopropanations
"Rhodium Catalyzed Asyimnetric 1,4-Addition of Organoboronic Acids and Their Derivatives to ' Synlett, 2001, 870. Electron Deficient Olefins," "Vinylogous Mannich Reactions. Seiectivity and Synthetic Utility," Bur, S.K.; Tetruhedron, 2001, 57, 3221. "Intramolecular Free Radical Conjugate Additions," Zhanc. W. Tetruhedron, 2001, 57, 7237. "Recent Advances in Catalytic Enantioselective Michael Additions," Krause.;Hoffmann-Riider, A. Synthesis, 2001, 171. "Reactions of Conjugated IIalocnoates with Nucleophilic Reagents," Caine. D , Tetruhcdron, 2001, 57, 2643.
SECTION 74F:
Cyclopropanations, including Halocyclopropanations
\
(i-Bu),Te
:
8) 83%
SiMq
Ye, S.; Tang. Y.; Dui, L.-X. .I. Org. Ch~rii.,2001. 66, 5717.
87% (96% de, 89% ee) Davies. H.M.1,; Townsend, R.J. J. Or#. Cliein., 2001, 66, 6595.
1. LiHMDS ,TIIF 2. cat c i r v r m
PhN'-Nksr
5
CI-I,=CII-NPhTh
Ph
0
71% (33:67 truns:cis) V . L ; de Vincente, J.; Connert, R.V. Org. Lett., 2001, 3, 2785.
212
Section 74F
Compendium of Organic Synthetic Methods, Vol 11
lo
1. Et02CCH2NH2*IIC1,TPPRh(1II) DCM ,HZO, -10°C
Ph-
Ph
2. NaN02, aq H$S04, rt , 4 d
CO2Et 62%
Barrett.;Braddock, D.C.; Lenoir, I.; Tone, H. J. Org. Chem., 2001, 66, 8260.
-
3 q Zn(CH21)2 , DME DCM, -10°C rt
Et*c3 Me?NOC,r,, n -
Et
B u
*
"tMo
Et
69% (86% ee)
MQNOC
C ~ W ~ A L A Jolicoeur, .B.; E.; Bydlinski, G.A.S. Org. Lett., 2001, 3 , 3293. CEIN2
RU catalyst pentme
90% (74% ee)
0
Barheris, M.; Perez-fieto. J, ; Stiiiha, S.-E.;
Org. Lett., 2001, 3 , 3317.
-* 4 ,
NC -.%Me3
SiMe,
1) 2.3 eqBuLi
2, L
B
r
65% (>98:2 E:Z)
3) H 2 0 Lnnger. P.; Freifeld, I. Org. Left., 2001, 3, 3903.
Me2
2. 1 .TfiO, 5 eq Dibal -78°C
Ph
2,6-lutidine
"%,p
fr 86~73% Et02C?3 Tavlor.;Engelhardt, F.C.; Schmitt, M.J.; Yuan, H. J. Am. Chem. Soc., 200Z, 123, 2964. Ph
Et02CCH=N2
-
A C 0 2 E t Ph tiis@ yr Lwly1)borate"opP"lf1) catalyst Diaz-Requejo, M.M.; Belderrain, T.R.; Trofmenko, S.; PBrez, P.J. J. h i . Cherli. Soc., 2001, 12.3, 3167. Ph-
97%>98:2
Section 74F
Cyclopropanations
Charette. A,]&; Bcauchemin, A.; Rancoeur, S. J. Ant.
Clieiii.
=
80°C
Furstner.;Stelzer, F.; Szillat, 11. J.
-
h i .
SOC., 2001, 123, 8139.
T s ,
10% RC12 , toluene
Ts-N
213
Q N
59%
Chtrrr. Snc., 2001, 12.3, 11863.
Ssha, B.; IJchida, T.; Katsuki. T. Syntott, 2001, 114.
N2C€IC02t-Bu,Co(1I) complex
A
Ph
MeOH , 5 % )1 1 2 0 , 50°C
4 C 0 , t - B ~ Ph
80% (83: 17 trcms:cis), 92% ee Ikeno, T.; Nishizuka, A,; Sato, M.; Yalnada. T. Synlett., 2001, 406.
1. Me-
IPh' OTf
NHSo2Ph
BuLi , TIIF 2. I N HCI J,ec. II.-Y.; Lee, Y.-11. Synletf, 2001, 1656. NZCHCO2Et. rt \ - hP
*
0
55%
phb
Ru catalyst, 2,4,6-~llidine
0,Et
-I-PhmO,Et
(30 70) 81% 70% et: 82% ee Zhene.; Yao, X.; Li, C.; Chen, II.; Hu, C. Tttr-uhedmn Lett., 2001, 42, 2847.
section 74F
Compendium of Organic Synthetic Methods, Vol 11
214
do
0
Metal salen catalyst, 1 d
-cl+
NMI ,'ITIF, rt
-
72% (98%ee) C1
CJchida, T.; Saha, B.; &&&J
'
T~tmhedmnLett., 2001, 42, 2521.
Tetrulierlrnn Lett., 200I, 42, 3369.
Fujiwarn, T.; Odaira, M.;
A
Ph
B
Me,SiCIIN2 , DCM , -20°C t [ RUZ(CO)7( p-OAC121
ph\a/siw3 +
SiMe,
68) 64%
(32
Maas.;Seitz, J. Tetrulwdron Lett., 2001, 42, 6137.
CIZCNCO2Me, 1,iHMBS THF , DBlJ
Escnbano.; .. Pedregal, c.;
; Fernhndez, A.; Burton,
a
62%
K.; Stephenson, G.A.
T(~truheclron.2001, 57, 9423.
+ \
Ph
N,CIICO,Et, DCM
c h i d Ru d e n catalyst
Yao, X.; Qiu, M.; Lu, W.; Chen, 11.;
*
4-
PhmCQ2Et
C0,Et (26 74) 82% 44 %ee 43% 133 Tctmhedron Asymitt., 2001, 12, 197.
Section 74F
Cyclopropanations
215
N,CI-ICO,Et, Cu(L)(OT!)
PhA \
L = dirunino biphenyls
*AT
COzEt
Ph
94% ( 8 4 18 hun.s:cis) (46% ee 57% ee) Sanders, C.J.; Gillespie, K.M.; Scott. P, Tetruhedron Asymnz., 2001, 12, 1055.
A \
P11
N2CMC02Et, Cu(OTfh [emiin] NTf2 chiral his-oxawline
- A Ph
CO2Et
38% (64 : 36 truns:cis) 6 0 % ~64%ee Fraile, J.M.; Garcia, J.I.; Herrerias, C.I.;m o r a l . J.& CaTie, D.; Tetruhedron Asyiiini., 2001, 12, 1891. in ionic Iiqluid
A \
N,CIIC02Et, Cu(1)khird runine
Ph
CI-ICl, ,reflux
m d C D z E t 61% (3753 cis:truns)
3 6 % ~40%ee Ma, .I.-A.; Wang, I-.-X.; Zhang, W.; a o u . 0_.-Id. Tetrul7erlron Asyntni., 2001, 12, 2801.
Q0
toluene, 200"C, 2 d scaled tube
I 0
<
k
Ph
74%
SdukLJ,; Siegfried, S.; Gordon, G.; Nieuwenhuyzen, M.; Allenmark, S. Eur. J. Org. Clzeni., 2001, 1951.
A
N2CHC02mnenthyl,HzO
Ph
cat[RuCl,(p-cyrne~ne),]~* ph~""'"' pyiidine oxazoline ligand k)I ue ne (97 I w ~ s ~ S.; I , Takezawa, F.; Tuchiya, Y.; N i s h i v d Clieni. Cnnimun., 2001, 59.
3 ) 62%
hv , acetone 85% Ramnauth, J.; Lee-Ruff, E. Cuw. .I. C'l?c,nl.,2001, 79, 114.
216
Section 74F
Compendium of Organic Synthetic Methods, Vol 11
6
BuJe+CH2Ph Br- , KO11 MeCN,rt, 1 d
d-
Guo, X.; Shen, W.; Shao, J.;
bPh
-
67%
*A
Synrh. Conmtirn., 2000, 30, 3275.
F , EtMgBr -+.rt Cp&iC12 -78"C+,T H0°C
81%
Gandon, V.; Bertus, P.; Sznnoniak. .I. Eiir. J. Org. Chein., 2000, 3713.
+,+
Rh2( S-DOSP)4 , -78°C t
pentane, PhCII=I12
N2
4Ph
60% (85% ee)
&'
C02Me
pw,,#t\'
C02Me
DdVitb.;Boehel, T.A. Totruherlmn Lett.. 2000, 41, 8189. >.
I
A
[ PllS
Ph
A
Takeda.;Takagi, Y.;
cXH
l
SMe3
A
7
Cheng, D.; Know, K.R.;
G
1. r-BuOK , BuLi , THF , -50°C
SPh
-
-
SiMe,
J
c8H17+
DCM,-40"C-z
rt
:
% =
0
J. Ani. Chciti. Soc., 2000, 122, 412.
(2,4,6- trichlorophe ny1)OZnCH21
A&;
5
Ph Saeki, N.; Fujiwara, T. Tetrulzedron Letf., 2000, 41, 8377.
2. LiBr 3 . reflux
ette.
84% (98:2 EZ)
/ CpzTi[(POEt3)]d
99%
90%
Francoeur, S.;Martel, 1.; Wilh, N. Artgrw. Chern. Ir~t.Ed., 2000, 39, 4539.
217
Cyclopropanations
Section 74F
o6 H
\
J S- - - C\,02BU
CO,B u
*
DMF , NaOAc
TBAB , 110°C , O h h CalO, v.;
’
*
60%
+ oy>
; Lopez, L.; Lerario, V.L. Tetrulwdron ,!.eft.. 2000, 41, 8977.
Me
Me
Q.)J-Pil*!<
t
0 3(
Yb(OTf)3,-78°C Ph E M THF , hexme
~‘~111,ll1
Ph Ph
(
Ph
1)
(10 Mamai, A,; Madalengoitia, J.S. Tttmhedron Lt~tt.,2000, 41, 9009. Mamai.
A \
Ph
84%
NZCHCOZt-Bu , TIIF, 1 d Co-salen catalyst catalytic
‘ Niimi, T.; IJchida, T.; Irie, R.; &&&J
: 2) 89% (98 Tetruhedron Lett., 2000, 41, 3647.
1. C P ~ Z ~ ( C H ~ = C IPMQ -I~). Ph Bertus, P.; Gandon, V.;
A
Ph
2. XI I-12S04 C h m . Corrznzun., 2000, 171.
N,=CHCO,Et ,I’hNO, ,40”C 1% Cu-Schiff base catalyst
U; Zheng, Z.; Chen, H. T~~truhedrorr Asyrirni.,
t
53%
A
Ph
2000, 11, 1157.
65% (91% ee)
218
-
Coinpendiurn of Organic Synthetic Methods, Vol 1 1
Et,Zn , DCM ,chiril sulfonamide
OH
Ph
Section 74F
*
Schiff hase ligand
Ph
88% (98% ee)
Balsells, J.; Walsh, P.J. J. Org. Chern., 2000, 65, 500.5
f'n
4Bu ,DMF ,152"C14%BHT
*
ferrocene Lbpez, S.; Trahnnco, A.A.; Fern6ndez-Acebes, A.; Flbrez, J. J. Am. Chcnl. SOC., 2000, 122, 814.5.
40% (89% de)
GO% (4: 1) b n v a l . V.&, Smith, H.W.; Mynd, G . ; Jones, R.V.H.; Fieldhouse, R.; S p y , S.E. J. Chern. SOC., Perkin Trons. 1, 2000, 3261.
,
C,H ,CIIO
%.J
-
'Ph
, THF
I""
*
Toratsu, C.; Fujii, T.; Suzuki, T.; Takai. K. & w v .
93% 58 OH: 4 2 d O H Chcrn. Int. Ed., 2000, 39, 2725.
Uchida, T.; Irk, R.; Xatsuki. T. Synlett, 199Y, 1793.
(93 97%ee
7) 45%
)
Section 74F
Cyclopropanations
N2CHCOzt-Bu
phy
219
,,,d COZt-Bu
CO,t-Bu
t
\P +h
5% Ru-salen catalyst (80 81% ee Uchida, T.; Irie, R.; U s u k i. T, Synlett, Z999, 1163.
20) 53% 51% ee
1. EtZZn , hv , CDzC12,rt 2. CHzIz ,0°C
..A I
MqS1
3. Ph-OBn
ChrlTCf(L.;Beauchemin, A,; Marcoux, J.-F. Tetruherlron Lett., 1999,40, 33. .
I
>95%
,
1. [ri(Oi-PrhCl/i-PrMgCl] etherhexme
A
*
2. PhCOzEt
IIIIIII
MqSi
OH
Ph
88% (93:7 truns:cis) Matsuda. I.; Takeuchi, K.; Itoh, K. T&-ul?edron In.tt., 1999, 40, 2553.
- phY CO2Et
NzCIICOzEt , 8 0 T bis iinide Cr(vI) complex
Jan, D.; Simal, F.; ; Noels, A.F.; Rufanov, K.A.; D.N. Tetruhetlron Lett., 1999, 40,5695.
J
N2
5% chiral feirocenyl ligand/Cu(OT!)2 DCE,rt,8 h
-
A*+< ,,,lll~~~
51% (63% ee)
Kim, S.-G.;Cho, C.-W.; A h n J L
Tetrul?etlron, 1999, 55, 10029. SnBq
Ph-CH(OMe),
'I'iCh , DCM , -78"C, 3 h Sugawara, M.;
90% (cidtmnr = 0.65) ; Gourevitch,
M.J . - i
*
Chcvn. Conintun., 1999, 50.5.
Ph
87%
220
Compendium of Organic Synthetic Methods, Vol 11
C02Me
Section 74G
,#*
chiral Rh(I1) catalyst, -5°C CIIz=CHOEt ,CHZCl2
N2
EtO 86% (79% ee)
Davies.;Panaro, S.A. Tttruhedron Lett., 1999, 40, 5287. 0
II
P:Tp7Ph
Yo
1. LDA , THF
*
2. t-BuOK ,Z-BuOH
)4,, +,*",
0
0
Nelson.,Warren, S. J. Chcni. Soc., Perkin Truns. I ,
4
Ph
63%
1999, 3425.
Ph2S=CHC0,Et, EDA
-
cat Rhz(0Ac)d
&COZEt Ph 38% (52:48 truns:cis)
Muller. P.; Femandez, D.; Nury, P.; Rossier, .I.-C. Helv. Chini. Actu, 1999, 82, 935..
SECTION 74G: CYCLOBUTANATIONS, INCLUDING HALOCYCLOBUTANATIONS
Chen, C.; Chang, V.; Cai, X.; Duesler, E.; Mariano. P.S. J. Ant. Clieiii. Snc., 2001, 12.3, 6433.
r
Me0 Chiha.
O
/
K; Miura, T.; Kim,
M
e
e73% MLS S.; Kitano, Y.; Tada, M. J. h i . Chern. Soc., 2001, 123, 11314.
Section 75
Alkyls from Misc.
221
8 hP' H
72% Baik, T.-G.; Luis, A.L.; Wang, L.-C.; a i s c h e . M.J,J. Ani. Chew. Soc., 2001, 123, 6716.
Cai, X.; Chang, V.; Chen, C.; Kim, H.-.I.;
>
''
Tciruhedron L.ztt., 2000, 41, 9445.
Et
Terao, Y.; Satoh, T.; Jvfiura. M.; Nomura, M. Bull. Clieni. SOC.Jpn, I Y Y Y , 72, 2345.
R E V IE W S : "Photochemical Dhnerization In Solution Of Heterocyclic Substituted Alkenes Bearing An Hcterncycles, 2001, 54, 475. Electron Withdrawing Group,"
SECTION 75:
ALKYLS, METHYLENES AND ARYLS FROM MISCE1,LANEOUS COMPOUNDS 6 eq PhI , BEt, , TIIF
air, rt , 10inin Liu, J.-T.; Jang, Y.-J.; Shih, Y.-K.; IIu, S.-R.; Chu, C.-M.; Yao. C.-F. J. Org. Cheiii., 2001, 66, 6021. NO2
Ph
85%
Section 75
Coinpendiuin of Organic Synthetic Methods, Vol 11
222
0
II
BuzCuCNLi,, TIP
/yOEt p OEt
&
Bu
74% (G7:33 sN2':sN2) J. Org. Cheni., 2001, 66, 5552.
Belelie, J.L.;
NO2
Ph
-* mP
20 eq i-PrI , 6 eq E t 3 N 2 eq (BzO), , ether, rt
9G%
Liu, J.-Y.; Liu, 1.-T.; Yao. C..-F, Tetruherlron Lett., 2001, 42, 3613. a t Pd(OAc),-2 PPh3
PhB(ON)2
*
83%
Ph-Ph
DMF ,90"C, 2h Wow. M.S.; Zhang, X.L. Tetrulwdron Lett., 2001, 42, 4087.
d
Pd(OAc)2, CuQz , 7 inin
SnB uj
THF ,23"C
95%
Me0 Parrish, J.P.; Flanders, V.L.; Floyd, R.J.; & K.W, Tetrulid-on Lett., 2001,4 2 , 7729. PhBFI- NBu,', aq DME
5% Pd(OAch, 5% dppb CS~CO , rt, ~ 12 h Quxh, T.D. Tctruhedron Lcjtt., 2001, 42, 9099.
u;
i
I-Ph
-
OTf
Ph3BiC1, , MtCN
90%
>
M
e
O
O
P
\ /
5% PdCl, , rt , 3 h
82%
S.-K.; Ryu, H.-C.; Kim, J.-W. Syntlz. Corrrnzun., 200Z, 31, 1021. Ph,BiCl,, MeCN
\ /
M e O e S n B u 3 -S.-K.;
* M
e
5% PdC12, rt , 3 h
Ryu, If.-C.; Lee, S.-W. Syntlz. Conintun., 2001, 31, 1027.
O
O
\ /
h
P
h
79%
(-+b
Section 75
Alkyls froin Misc.
0
223
1. PhI, Cat pd(0) 76%~ 2. incpha , DCM , 0°C
MezN
3. cat Pd(acac)z , i-PrMgBr TI4F
/
90% ee
de la Rosa, J.C.; Diaz, N.; Carretern. J.C. Tetrul?edronL,ett., 2000,41, 4107.
I'h,TeC1,, 1% PdCI, M
e
O
O
\ /
&
h OTf
* M e O G F ' h
3 eq NaOMe , MeOWMeCN 1t,7h
\ /
88% b g . S.-K.; Lee, S.-W.; Kim, M.-S.; Kwon, H.-S. Syntlt. Conmun., 200Z, 31, 1721. NuBPh,
PhSiCl2, MeCN ,rt
Sakurai, H.; Morknoto, C.;
*
Ph--Ph
C h m . Lftt., 2001, 1084.
76%
NCS , TMU ,cat PdC12(PPh3)2 COzMe C02Me
94%
Hossain, K.M.; Kameyama, T.; Shihata, T.; Takn,.i&. Bull. C h m . SOC. Jpn., 2001, 74, 2415.
PhTtClz, 10%~ PdCI,(PPh3)2
2
NaOMe , DME-Ii20 50"C,5h
htg, S.-K.; IIong, Y.-T.; Kim, D.-II.; Lee, S.-II. J . Chrnt. RES.(S), 200Z, 283.
2
cat PdC12(PPh3)2, NCS 45"C, 10 h
Q-0 C0,Me
Hossain, K.M.; Shihuta, T.;
Synleff,2000, 1137.
68%
84%
224
Compendium of Organic Synthetic Methods, Vol 11
Servino, E.A.;
M
e
Wang, I.;
95% (9:l an2i:syn)
Orx. Lctt., 2000, 2, 3039.
\ 0/
+
0)zI BF4 -
Section 75
PhMgBr ,GI t Pd(PPh,),
* M
d
ZnClz, THF , rt
e
\ /
P
h 86%
Chen. Z.-C. Synih. Comtrrcn., 2000, 30, 3607.
ii N
Ph<
hv , PhH , AICI,
P hCH2Ph
96%
Moss.; .. Fed6, J.-M.; Yan, S. J. Am. Clieni. Soc., 2000, 122, 9878 10% C ~ c 1 2 , 0 . 152 , DMF , 10O"C, 4h 2 PhSnBu, + P h-Ph W g . S.-K.;Baik, ?'.-C.; Jiao, X.H.; Lee, Y.-T. Teiruhc.drontuti., 1999, 40, 2383:
N z* B F4-
a
Ph-BF,K, dioxane
S% Pd(OAc), ,3.7 h
88%
Darses, S.; Michaud, G.; Genet, J.-P. Eur. .I. Orb'. Chenz., 1999, 1875.
S
93%
PhI, 5% silica-supported Pd
SnBu3
*
aq MeCN , 8 0 T
Kane.;Baik, 'T.-G.; Song, S.-Y. Synleit, I Y Y Y ,
80%
327.
PhJ' BF4- , NMP ,70"C SIlBU,
m P h S
*
79%
10% Ni(acac), , 8 h K~~&&Ls.-K.; Ryu, H.-C.; Lee, S.-W. J. Cliem. Soc., Perkin Truns. 1, 1999, 2661. ph-
IIu, Y.; Yu, J.; -;
CsIIIIZnI,THF
+
p
h
~
C
5
mianwaves Wang, J.-X.; Yin, Y. Synth. Comimn., 1999, 2Y, 1157.
H
l
l
80%
Section 75
Alkyls from Misc.
225
PhBF,K, 5% Pd(OAc), , DME
P h21+BF,-
GOT, 1h
*
Ph--Ph
99%
Xia, M.; Chen. Z.-C, Synth. Cnriiniun., 1999, 2Y, 2457.
M
e
\ a /I +
O
PhPh(OAc)3 ,CNC13 P
h BF4-
5% Pdz(dba~*CIlC13 *M 2 eq NaOMe ,rt , 3 h
e
O
O
\ /
P
S.-K;Choi, S.-C.; Baik, T.G. Synth. Cornnzrcn., I Y Y Y , 2Y, 2493.
h 75%
REVIEWS:
"RecentAdvances In The Transition Metal Catalyzed Regioselective Approaches To Polysubstituted Benzene Derivatives," ' . Yamamoto, Y. Chem. Rev., 2000, 100, 294. "New Mitsunohu Reagents For Carbon-Carbon Bond Foilnation," Itci.;Tsudoda, T. Pure Appl. Cliiwi., 1999, 71, 1053.
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 6 PREPARATION OF AMIDES
jj
SECTION 76: AMIDES FROM ALKYNES
0
toluene heat
+
/"
Et
Et
Rodriguez, D.; N ~ v u ~ w - V ~ Z C IA.; U ~Castedo, Z., L.; J . Am. Clzetn. Soc., 2001, 123, 9168.
F4CO)S
1. NaBI-Id, ALOH 2. PhCaCI-I
7
*
3. B uNH, 4. cucl,*2 H 2 0
; Sad,
.
' 4.3) 56%
c.
do 55%
0
Remeshkumar, C.; periasamv. M . Synkrt, 21100, 1619.
N
I
Bu
SECTION 77: AMIDES FROM ACID DERIVATIVES 0
1. 2 q L D A
70%
2. PhCN Chen,Y.; Li, T.; Siehurth, S.Mc.N. J. Org. CIIPIII., 2001, 66, 6826.
Ph
Amides froin Acids
Section 77
227
C O ~ H , toluene
-1 ~
\ I
5 7 ~ c ~ F 3 ( 0 1 1 ) 2, reflux 1h
0
59%
F3 c Ishihara, K.; Kondo, S . ; Yainamoto. H . Synlett, 2001, 1371.
86% Ph NHOMe NH,OMe Ci , MeCN , NEt3 , 3 h Bailin, M.A.; Chinchilla, R.: Dodsworth, D.J.; Ntiiera. C, Tetruhedron Lett., 2001, 42, 5013. Ph
011
O z N O C O z H
2 eq polymer-supported carbodiimide 3 y polymer-supported DMAP
Lannuzel, M.; b ) t h e . ;&'I
Perez, M. Tetruhedron Lett., 2001, 42, 6703.
CO,H -
Ph-
M%N-HCI, piperidine NEt, ,0"C MeCN, 3 h
Wakasugi, K.; Nakamura, A.;
-AND
Ph
I K ~
92% Tctruliedron LZtt., 2001, 42, 7427.
( y c o C02M
96%
-
DCM , DMAP , 3 h 0°C -+ rt
A.C.; Iloffmann, R.W. Synthesis, 2001, 243.
75%
Section 77
Compendium of Organic Synthetic Methods, Vol 11
228
1. polymer-bound PPh3 ,DCM 5 q CC13CN, rt , 3 h
PhCOOII
-
0
It
75%
2. PhNHz Ph polymer- hound moipholine Buchstaller. H.PL;Ehert, H.M.; Anlauf, U. Synth. Conznzun., 2001, 31, 1001.
@:
H 2 N C H 0 , microwaves
/
*
97%
/
2 nun
0
0
Peng, Y.; Son.
G.; Qian, X. Synth. Conitnun., 2001, 31, 1927.
P hC02H
0
-
-
-0
PhM , / O M e
Bu~P ,NEt3, DCM, 16 h (Me0)Me NH=HCl Smith, J. Syntli. C O / ~ J / ~ 2001, J I M . ,31, 201 1.
;-
\
80%
xpM Me
PhO PhOCI I2COzI I
1 . C g C C N , PPh3O"C
2. PMPCH=NPh , 0°C
-+
it
*
Govande, V.V.; Arm, M.; Deshmukh, A.K.A.S.; Bhawal. B.M. Synth. CO//J//ZUn.,2000, 30, 4177.
0
Lee, W.S.; Park, K.11.; Yoon. Y .-J. Synth. Co/nrnun., 2000, 30, 4241.
Ph
92%
Ph P I 1 b N O P M P , CH2Cl2 , 12 h
Ph-cozll
NEt3 , triphosgene , -40°C: -+ rt
Krishnaswluny, D.; Bhawal, B.M.; Desmukh. A .R.A.S.Teiruliedron Lett., 2000, 41, 417.
61%
Section 71
Aniides from Acids
229
8x, 0
1. 2 eqBuLi , 2 e q NI-IEtZ
*
2. EtCN Brun, E.M.; Gil, S.; Mestres, K.;Parva.
Ii
65%
Synrke.sis, 2000, 273.
n s J p Y+ PI%-
hMe2
0
PhCOzl I
83% NHdCl , DIEA ,DMF * PhN'H; it , 30min Bailen, M.A.; Chinchilla, K.;Dodsworth, D.J.; N j c r a . C , Tctruhcdrnn L t t f . , 2000, 41, 9809.
A
Ph
di-(2-pyridyl)cxlionate, D M M , ether ~
Ph) y N H B n
BnNIl, , rt
CO,M
0 91% &ma. I.; Suenaga, Y.; Nakano, M.; Mukaivam a. T. Bitll. Ckerit. Soc. Jpn.; 2000, 73, 2811.
n HMDS IINW , 110°C N I 1 (neat)
*
O
y
r N
0 0 93% Chou. W,-C,; Chou, M.-C.; Lu, Y.-Y.; Chen, S.-F. Tetrulicrlron Lett., 1999, 40, 3419.
Br
0 \ /
1. 2i "1t , PPh3/2 lh eq CCl3CN
C0,H 2. O N I I y H I NEt, ,rt
Jug.D.O.; Park, D.J.; Kim, J. Tetruhccirorz Lttt.,
\ /
&N'r Br
I Y Y Y , 40, 5323.
J
P 90%
Section 79
Cornpendiuin of Organic Synthetic Methods, Vol 11
230
Al
NEt3, DCE ,2O"C , 1 h
x
*
PhO Milan, D.S.; Prager, R.11. Artsf. J. Chenr., 1999, 52, 841.
PhO
93%
NEtz
SECTION 78: AMIDES FROM ALCOHOLS AND THIOLS PhCH2OH
Mg(I-IS04)2 , PhCN
-
PhCII2NHBz 91% 90°C. 1.5 h ; Zolfigol, M.A.; Keyvan, A. Synth. Cotnmun., 2001, 31, 1947. Fe(CXO,), , SiO,
SakhiJ
MeCN ,reflux, 30 inin Ph Ph Motlagh, A.R. Synth. Coninrun., 2000, 30,665
Ph
Fe+3-Mont~norilbniteK10
* P hCH2NH Ac MeN ,70"C, 20 h kakourai. M.M.: M o v a s s U ; Fasihi, J. Synth. Cornniitn., 2000, 30, 821. PhCH,OII
90%
SECTION 79: AMIDES FROM ALDEHYDES
Ramalinga, K.; Vijayalakshmi, P.; &.&JwI.
PhCHO
T.N.B. Synlett, 200Z. 863.
1 . B OCNH2 , T s N ~, XIMtOH mxqr , rt , I d
+
PhCHzNHBoc
6~~73%
2. NaBH4, TIIF, r t Bernacka, E.; Klepacz, A.; Zeierznk. A. Tetmhedron Lxtt., 2001, 42,5093. PhCtIO
A I 2 0 3 , MeS03II.
NH40H31Cl
140"C, 3 h ShJrthl.; . , Sarvari, M.H. J. Cher1i.Re.v. ( S ) , 2001, 446.
Ph
NH2
95%
Section 79
PhCkIO
23 1
Amides from Aldehydes
/jtco~.B
1
, McCN , heat
96%
,M~(OAC)~*~I-I~O 0 H2N NI+ H 2h Kumar, K.A.; Kasthuraiah, M.; J W d v . C.S.; Reddy, C.D. Tctruhedron Lett., 2001, 42, 7873.
PhCIIO
OH
,NM0,KzC03
cat
Tillack, A,; Rudloff, I.;
A '9
Ph
[ R h ( ~ d hBF, ] , toluet~e 140"C, 20 h
96%
E m . J . Org. Climt., 2001, 523.
Yidav. J.S.; Reddy, B.V.S.;Reddy, K.B.; Raj, K.S.; Prasad, A.R J. Chcni. Soc., Perliin Trans. I, 2001, 1939.
<~""
Ph,P=C=C=C=O,THF , 2 d
Y
NI-I
Me2CIICM2NtI,
0
Schohert. R.; Siegfried, S.; Gordon, G.J.J. Chein. Snc., Pcrkin Truns. 1, 2001, 2393. B uC110
l.p-TolSOzNa, IICOOII , HlO
PhSOSJ H, 2. NaIICO3 , II,O/CII2Cl, Chemla..;FIehhe, V.; Normant, J.-F. S y n h s i s , 20U0,75.
BuCH=NSO2Ph
66%
Section 81
Compendium of Organic Synthetic Methods, Vol 11
232
SiMq
PhCHO
NHC0,Et
,T K l O l , 0°C
96%
Me, SiNH C02Et Ph Niimi, L.; Serita, K.4.; Hiraoka, S.; Yokoz;rwa. T. Tctruhorlron Lett., 2000, 41, 7075.
SECTION 80:
AMIDES FROM ALKYLS, METHYLENES AND ARYLS NO ADDITIONAL EXAMPLES
SECTION 81: AMIDES FROM AMIDES Conjugate reductions of unsaturated amides are listed in Section 74D (Akyls from Akenes).
1. I i , NH, ,TIIF t-BuOH , -78°C:
N-Me
2. Me1
Guo.
Z.;Schultz,
%
Me
70%
A.G. J. Org. Chctii., 2001, 66, 2154.
Me
5 % ~Pd(OAC)z, 5% P Q , 1.5 eq NaOt-Bu , dioxane
70T,5 h
I Me
G8%
Lee, S.; IIartwie. J.F. J. Olg. Chemt., 2001, 66, 3402.
Me
1. BuLi , ‘IIW , 0°C , 15 inin 2. Me1 ,0°C MacNeil, S.L.; Familoni, OB.; SO,NI I2
’
’
.. V , J. 0 1 - g . Chern., 2001, 66, 3662.
1. rBuOC1, NaOH , 1 1 2 0
2 . P T Ai tB, ,1Mh e C N , i t , l d
Dauban. P.: Dodtl. &1l, Tr.truhdron Lett., 2001, 42, 1037.
*
psoz N
70%
Section 8 1
Anides from Amides
b
y
o
HN*
233
-9
B=(r-,+,
cat Pd2(dba)3 ,Xatltphos , 16 h toluene, 120°C
0
OIIC
87%
Cacchi.; Fabrizi, G.; Goggiamani, A,; Zappia, G. Org. Lett., 2001, 3, 2539.
PhY
1. BuLi, (-)-sparkine toluene , -7X"C
M e O ON \ B o c
2.
t
OP+
02N
90%r(94:6 dr)
1. MqSiCl, LHMDS NEt, i - P r M % y L N I B o c2.
Mohamed, M.:
+
i - P r M % S y
c
3. 1N HCl
S i Me C Pr
MeOzC NfiBoc
MtO2C
122 Tetruhedron Lett., 2001, 42, 19 1.
S
NHBoc
1) 60%
0 2
H 2N-
N 'Boc
Ac'
J. Ant. Cl?eiri.Soc., 2001, 123, 1230.
Johnson, T.A.; Curtis, M.D.;
L
Ph
0 2
2% R ~ ~ ( O A,C PhI(OAc)z )~ 2.3 MgO , CH,Cl,, 40°C
90% Espino, C.G.; Wehn, P.M.; Chow, J.; DuBois. J. 1.Am. Chem. Snc., 2001, 123, 6935.
li
1. LDA
0
2. MqSiC1 * ~ t jA ~ Ni A o M e 3. CsF, 145"C, Et3SiCl Me 61~84% Cunico, R.F. Tctruhetlron h t t . , 2001, 42, 1423. H
N -0Me
I Me
I
Compendium of Organic Synthetic Methods, Vol 11
234
I . 2 ' ~TEl4 1 ,CHzClz ,20"C 2. H2/Pd-C1 EtOH Bu,SnH, AIBN
0
5-
3. Na/NH3, EtOII , -78°C
0
Section 8 1
% 85~98%
dNH2 PhI(OzCCF,), , 1.5 h
aq MeCN
96%
Yu, C.; Jiang, Y.; Liu, B.; Hu. 1.. Tetruh~~dron Lctt., 2001, 42, 1449. Et2Zn, 2 eq ClCII,I, tohene , rt 2 eq tetrahydrothiophene, 16 h
AN
*
Ph
~
68%
Ph R.A.; Jones, R.V.H.; Fieldhouse, R.; Blacker, J. Tetruherlron Lett., 2001, 42, 1587.
cp"
H
I
PhCIIzCl , CszCO3 , TBAI
""yo?
~
0 : r DMF , 2 3 " C , 5 h
0
P d " K O ' / l
Ph
0 98% Ph Salvatore, R.N.; Shin, S.I.; Flanders, V.L.; h c . K.W, Tetruherll-nnZxtt., 200Z, 42, 1799.
C02Me
toluene, I C f l U X
86%
Sh
0
PMP
AICdldt.; . . Rodriguez-Ranera,C.; Rodrigucz-Vicente, A. Tetruhedron LEN., 2001, 42, 3081.
Section 81
235
Amides froin Amides
e- , EtMgCl , ether
N
N
~
I C02Me
I
-72"C, 20 11611
65%
C02Me Suga, S . ; Okajima, M.; Yoshida. J.-iTetruherlron Lett., 2001, 42, 2173.
,Ts
h(OTf)3, PhfI, DCM it,45h
Ph Yadav. J.S,; Reddy, B.V.S.; Rao, R.S.; Veerendhar, G.; Nagaiah, K. Tetrulierlron Lett., 2001, 42, 8067.
Tf
m S i C P r 3
BF3QEtz, toluene rt , 30 inin
. .
;.T-
72% (56:46) Sugnno, M.; Kagoshima, 11. Tetrulic~droiiIxtt., 2001, 42, 3889.
XNP
30% BuBr ,CI12C12,rt N(CH2-2-pyidyl), , 1 h
Br
O
Clark.
Sii-R-3
I
Bn
*+J)
96%
a; Battle, G.M.; Bridge, A. Tetruhedron Lett., 2001, 42, 4409.
Bn
, 57, 748 1. Katohgi, M.; ~ T e t r u h c d l o n2001,
1 . 2 eq NaII , DMF 0
Ts
0
2. 1,34iiodopropane
Costa, A,; u e r a . C,; Sansano, J.M. Tetrulierlron Asyinin., 2001, 12, 2205.
60%
Coinpendium of Organic Synthetic Methods, Vol 11
236
Section 81
SiEt3
hk
5% Pd(OAc), , 10% dppe NaH ,DMF ,100"C
O
AcO
I
0
N 90% Bn NAsiEt3 Bn Polr.;Giamhastiani, G.; Malacria. M.; Thorimhert, S. Terrulzedron L m . , 2002, 42, 6287.
D
N
02s
I
O PhSnMe3 2 , 10 eq LiF 3% Rh(XXXCzH4)Z t
R-Meo-MOP , 12 h dioxane , 110°C
75% (88% ee)
JPh
Ph>I4
; Ishigedani, M. Tefrukcdron. 2001,
fI i
0
I
N
CQEt
COzMe
Ph 57, 2589.
1. MqSiCHNz -1 00°C
2. ultra.sound AgC0,Ph
*LA 0
C02Et
I
53x54% CO,Me &uU. 1 G . C Saint, R.E.; Saint, S.L.; Chamhers-Asman, D.M Synthesis, 2001, 247.
Li , T H F , -78°C. 3 h
44'-di- terf-hutylhiphen yl
+NHOMe
Yus. M.; Radivoy, G.; Alonso, F. Syntlwsis, 2001, 914.
A
0
CII,(CN)2 , KOII , DCM
NI IPh
Bu,N €KO, ,i t , 3 h
Dave. C . G ; Parikh, V.A. Syntli. Corrititun., 2001, 31, 1301.
dN
0A N/z NH~ I
I
Ph
60%
Amides from Anides
Section 81
1
3eq
231
s\\ PEt @ N A H
-
95%
N ' Me2 200"C, toluene, 15 mill Ph microwaves Lev.; Leach, A.G.; Storer, K.I.J. Clieni. Sor., Perkin Truns, 1, 2001, 358.
Ph
NMe,
se r'il
4 q rncpba , 8 eq NaII
i-PiOoII ,rt N MBz Ward. V.R.; Cooper, M.A.; Ward, A.D. J. Chern. Soc., Perkin Trans. I, 2001, 944
B toluene, u 3 s n Hreflux 3 J 3 N _ I1
&;yJL;h
54% El Bialy, S.A.A.;Ohtan, S . ; Sato, T.; Jkeda. M . Hoterocyclcs, 2001, 54, 1021.
Is.
'*
5 eq L D A , ether 'I'sIIN N &
-78°C
Arjona, 0.;Menchaca, R . ;
85%
27%
2-R +
a I Hcrorocycles, 2001, 55, 5 .
60%
Bothe. U.; Rudheck, 11.C.;Tanner, D.; Johannsen. M. J. Chern. Soc., Pcrkin Truns. I , 2001, 3305. N -Ts
MeMgBr , 'lI~IF-t(>lUel1e chiral Cu catalyst , 0°C
Muller.P.; Nury, P. Hdv. Cliini. Actu, 2001. 84, 6 6 2 .
N HTs 52% (91% ee)
Compendium of Organic Synthetic Methods, Vol 11
23 8
Section 8 1
*A Ts
PhCI-kN-NTC Na' , 1%Rhz(OAc)4
P hCII=N-Ts
20% sulfide,40"C , dioxane 10%chiral BnNEt,Cl
Ph
4%,*
Ph
68% (2.5:1 1runs:cis) V . L ; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Procelloni, M. Angew. CIIW. rrrt.~ d .2001, , 40, 1433.
L
BnO
'c
-78°C
'-t
0
Lindstriim, 1J.M.;
' '
p+ 6
2 eq LiIIMDS , DCM 12
85%
CIz~nr.Eiir. J., 2001, 7, 94. , BF,*OEtZ Ph
PhA
N\
Ts
Ungureanu, I.; Klotz, P.;
-
1111l11l11
DCM ,-78°C
TsHN
Ts (1 . 1) 45% Angcw. CIiem. Int. Ed., 2000, 3Y, 4615.
Ph
GNL
1 . B uLi , TI-IF , -78°C
2.-78"C
'-t
It
*
/ A Br Ph Ph 98% (9.8:l de) He, S.; Kounin, S.A.; Rawal. V.H. J. Am. CI?em.Snc., 2000, 122, 190.
Frank, K.E.; Auh6. .I. J. Org'. CIiern., 2000, 65, 655.
Section 81
Aniides from Anides
239
/o-””
6 02s
I
02s
PhSnMq , LiF , 110°C
I
*
3%) R ~ ( x x ) ( C , I I ~ ~ 6% R-MOP , dioxaie , 10 h
FF
s . .. Ishigedani, ; M. J. Anz.
F3 CI7~~1ll. Soc.,
c
2000, 122, 976.
5%) TBAF, T I I F , 4 h
N-Ts
>99%
M q S i N , , rt
Wu, J.; HPU. X.-L; Dai, L.-X. J. Orx. Chelii., 2000, 65, 1344.
NI ITS
5% TiC14 , CHCl, SiMe2Bn
rt,3.3 h
93%
Miura, K.; Hondo, T.; Nakagawa, T.; Takahashi, T.; IIoso
78% (54:46 cmti:syn)
1
.
urd2.; . Trogolo, C.; Umani, I;. Org. Lett., 2000, 2, 401. 3
PhS0,NIIEt Katohgi, M.; Yokoyama, M.;
PhI(OAch, 1 2 , I X E , 3 h t
ultrasoutid ,40°C Synlett, 2000, 1055.
PhS02NH2
71%
Section 81
Compendium of Organic Synthetic Methods, Vol 11
240
t-BuSOCl , DCM i-Pr,NEt, (PhSc), rt
-5O"C-,
*b
+
S
e
€
h
59%
Lin, X.; Stein, D.; Wcinreb. S.M. Tetrulicdron I x t t . , 2000, 41, 2333.
@ CI - b - = N
0
Bn
'
90%
BF3-OEt,, DCM
Bn
Bt = benmtiiazol-I-yl Mehta, S.; IIe, H.-Y.; Cui, X. J . Org. Clierri., 2000, 65, 4364.
N-SO2Ph
II
NHSO,Ph
PhMe,SilI , 10% B(C,F,),
AII
b
toluene , rt , 3 0 inin PhA 1 3 93% Ph 11 . Blackwell, J.M.; Soninor, E.R.; Scoccitti, T.; Piers. W . E Or8 k i t . , 2000, 2, 3921.
m
PhA ' N -SO,P h
B
r
,In
NIISOzPh
THF Lu, w.; cilaLuL J. Org. Cliern., 2000, 65, 8589.
'
Ph
v M&
2.5
N -Ts
99%
Ph
MqSiCH=Nz 72% ( 9 5 5 cis:trans)
dioxme ,40"C
cat [Kh(cod)MeCN),]BF~ , dioxane
2.H20
IJeda, M.; Snito, A,;
I
)r
Me0 Synkrt, 2000, 1637.
Section XI
Anidcs froiii hrnides
241
Me
I
Me
I
BF3*0Et,, toluene inimwaves 54-56°C
1 ) >99%
(999 Cardillo, G.; Gentilucci, L.; Gianotti, M.; Tolornelli, A. Synlett, 2000, 1309.
Wu, Y.-L.; Chuang. C.-P.; Lin, P.-Y. Tc~truhedr-on,2000, 56, 6209.
-1,
O Y T B n
2'Me1
0
+
(&f'T0x7 "'%,,,,
1 . LHMDS , - 78°C
-
(93
o&
Bn
Bn
7) 65%
JqB
Bull, S.D.;m e s . S.G,; Nicholson, R.L.; Sanganee, H J . ; Smith, A.D. Tetruherlron A,~yiiiiri.,2000, 11, 3475.
llrLB*' 0
0
COZMe
3 eq A d N *I
Na(0AchBH. MS 4A DCE, 15 h , 0°C -.+ rt
0
Ph
Beshore. D.C.; Dinsmore, C.J. Tetrulicdron Lett., 2000, 41, 8735.
64%
Compendium of Organic Synthetic Methods, Vol 11
242
Et,Zn ,Cu(OTf), ,toluene
Section 81
98% (93%ee)
Ph-N-Ts
chirlll phosphine ligand ,02 Ph J. Am. Chern. Soc., 2000, 122, 12055.
Fujihara, H.; Nagai, K.;
PhSi(OMe)3, DMF Cu(O A C ),~it
+
61%
0 0 P.Y.&; Deudon, S.; Hauptinan, E.; Clark, C.G. T~~truhcdron Lett.. 2000, 42, 2427. Me&
TOO,\
Me,SiCIIN,
Ni Ph 3h
N-SOZTol
Ph
75%
Tetruhedron L.ett., 2000, 41, 9455.
Mori, R.;
jiNlih a9shyf:urai Cxo's ackl/Si02, MLCN
Ey10 v ,Ph ,.'
'
. ... .
. M.M.; Ghodrati, K. Syntlt.
* Ph Cornnlrm.,2000, 30, 2353.
*li:
, 3 % Pd(PPh3)4,THF
F hCH=NTs
rt,lh
Shim, J.43.;
)to. Y.
Hetororyrles, 2000, 52, 885.
97%
Bn
(TMS),SiH, AIBN , PhH reflux , 3 h
+
Quirante, 1.; Escolano. C . ; Diaha, F.; &QQ&J.
Heterocycles, 1999, 50, 731.
i4%
Section 81
Amides from Amides
6-11
243
d
PhBr , P ~ ( O A C )dppf ~, , 2 d NaOt-Bu , toluene, 120°C
N-Ph
*
Shakespaare, W.C. Tetr-uhedronLtt., 1999,40,2035.
82%
PhCHO ,?'FA, Et3SiH PhJ
toluene , 120°C. 36 h
NH2
P
~
h
d N -Ph
I
92%
DuhB. D.; Scholte, A.A. Tetr-ulidrnn Lett., 1999, 40, 2205. C02Et
I
PhvC1 / I I
Bu$nH, AIBN , toluene, heat
0AN?
C0,Et
J&
--
0 79%
H OTB DPS
OTBDPS
dr (8.9:35: 1 ) Bryans, J.S.; Large, J.M.; parsons. A.F, Tetruhcdron La., 1999, 40, 3487.
r-Buh1 . 2 q BuLi, TIIF, -78°C 2. BnBr
3. 10% oxalic acid, iEflux h:x
rt
*
9 Ph
B
n
Bu 72% (73% ee)
Hdnson.; . . Prohst, D.A.; Robinson, R.E.; Yau, M. Tctruhedrnn k t t . , 1999, 40, 4761.
Blass.
k;Drowns,
83% M.; Hanis, C.L.; Liu, S.; Portlock, D.E. Tetruherlron Lett., 1999, 40, 6545.
244
Section 8 1
Compendium of Organic Synthetic Methods, Vol 11
0
II
0
II
+
t-Bu/ S \ ~ ~ i ,
M
I
2. NuBI14, -48°C
Borg, G . ; Cogan, D.A.;
PhIIN Yang, Y.;
t-Bu/ S L N A P h
Tetrulrcdron Lett., I Y Y Y , 40, 6709.
78% (96:4 dr)
, MezNII , t o l u e ~ aubclave e
N UPh 160°C Org. Prep. Proceed. Int., I Y Y Y , 31, 559.
C%u3SnHI
irflux , 65°C AIf3N, PhH
PhHN
75%
N&Z
k1
*
..
/
/
_.
OMe 65% (1: 1) Xkeda. M.; Shikaurn, J.; Mnekawa, N.; Daibuzono, K.; Teranishi, €1.; Teraoka,Y.; Oda, N.; . ‘h. . . Hmrocycles, I Y Y Y , 50, 31.
I
Me Lee. Y . L ; Suk, J.Y.; Kim, B.S.Tctruheclron k t t . , I Y Y Y , 40,8219.
58%
S.W,; Lin, S.-I.; Vice, S.F. Tetrulwilron Lett., I Y Y Y , 40, 8767.
OMe
+ Me'Nx
Section 81
Amides from Amides
qBr AIBN, Bu,SnH toluene, 60°C
245
+
Me
0
Me 0
1)
Jones.; Brunton, S.A.; Gosain, K. Zetruherlron lxrt., 1999, 40, 8935. PhSnMq ,THF ,60"C, 19 h Ph6
N -Ts
2%) [Rh(cod)(MeCN)z]BF~
NHTs
Ph
98%
Qi.& Moro, M.; Ihkuhara, 11.; Kawanishi, T.; Inoue, Y. Tetruliedron Lett., 1999, 40,9259. ,Ts
plyinethyl hychwiloxane
-
Pd-c , €3011
I, h\,x''
NHTs
Ph
F
96%
Chandrasekhar. S . ; Ahmed, M. Trtrulwrlron k t t . , 1999,40,9325.
NHTs
MeMgBr , 30%~0 1 , 1.5 h
ll~iiil~
N-Ts ether
* QMe 52% (91% ee)
Muller.; Nury, 1'. Org. Lc,tr., 1999, 1, 439.
(with lo%,cat - -91% & 25% ee)
1 . PhLi , AlMq 2. IIClMeOII
t-Bu
i- Pr
-
3 . BzCl, NEt,
Cogan, D.A.; J?llman. J.A. .I. Am. Chem Soc., 1999, 121, 268. NIIBn
3 . 3 % ~Pd(OAc)2 , 5 % MOP KZCO, , toluene, 36 h
100°C
=
Ph
H 65~80%
Do
MOP = 2-imthoxy-2'-diphenylphosphino-his-l~is-l, 1'-biphenyl Org. Lett., 1999, 1, 35. Yang, B.11.; Buchwald.
\
246
Compendium of Organic Synthetic Methods, Vol 11
Me
0
Section 82
1.3.2eq LHMDS 3.2 eq LiCl , TIIF, 0°C 2. Me1 ,O"C , 1.5 h
613
Me
Me
91% (93%de)
u; Schnider, P.; Kwon, S.; Kung, D.W. J. Org. Chern., 1999,64,3322. 1. BuLi, (-)-sparkine ether , -78°C , 2 h
MqSn
1
f
N\
2. -25°C , 1 h
& I
t
Ph
BOC
BOC
41% (X9:ll er) Serino, C.; Stehle, N.; Park, Y.S.; Florio, S.; Beak. P.J. Org. Chern., 1999,64,1160.
REVIEWS: "Synthetic Catalysis of Amide Isomerization," Cox,C.; Lectka. T. Res., 2000, 33, 849.
Accts. Clwrit.
SECTION 82: AMIDES FROM AMINES
NH2
Ph
H
BnCI ,C O Z ,C~2C03 >
96%
Ph- " K O B n
TBN,DMF, 23"C, 5 h
0
Salvatore, R.N.; Shin, S.I.; NagIe, A.S.; Junp K .W. J. Orb. Chem., 2001, 66, 1035.
Tr
\
N
(>\/oms
TFA, Et3SiI-1, DCM l h
H
\
= - N
&oms
Y~QSJL;Klapars, A.; Warner, D.L.; Weiss, A.H. J. Org. Chem., 2001,66,7542. Ph2C =N-OH
f-BuSOzCl,ether, NEt3
-35°CI't Artmann 111, G.D.; Bartolozzi, A,; k k . R.W. : W&eh.
t
85%
P h2C=N S O f-Bu
S.h.I. Synlett, 200Z, 232.
Arnides from &nines
Section 82
241
PhCI-I(C0zEt)2,mimwaves PhNI-Iz
83%
15 inin ;- .
0 Veiveer, P.C.; Osnahrug, S.J.M.; Visser, G.M. Tetrulzerlron I A t . , 2001, 42, 1367.
0
H
6 '' 1
1. NaIIMDS ,THF
I F
3
C
v
0°C + I t , 2 I1
N
H
*
z 2. PhCOzMe
Ii&
94%
0
Wane.; Rosingana, M.; Discordin, R.P.; Soundararajan, N.; Polniaszek, R. Synlett., 20191, 148.5.
1, o
NIIz
l r ~ o z c N i m
NEt3 , CHzClz , 20 inin
* e N " N H I1 2
2. H2/Pd , AcOII
Liu, Q.; Luedtke, N.W.;
NI 12
Ph
92%
m.Tetrulwlron LL)ft.,2001, 42, 1445. 1. C S ~ C , O ~ , Me1 ,23"C TBAI, DMF
2. BnBr , Cs2C03 87%
Salvatore, R.N.; Ledger, J.A.; Junrr. K.W. Tetrulzedron Lett., 2001, 42, 6023.
I Me
OB n
Ly
VomDMs DME , acetone, CO
N
OTBDMS
4 h , 100°C 0 quant cat co2(co)8 Bn Davoli, P.; Forni, A; Muretti, I.; Prati.;Tome, G. Tetruliedr-on, 2001, 57, 1801.
I
PhCIIzNIIz
BnBr , CO2, DBU , I 1 2 0
BnNIICOzBn 6%
u; Shen, Y.-M. Helv. Cliiiit. Actu, 200Z, 84, 3357.
+
PhCHZNBnz 60%
Coinpendiuin of Organic Synthetic Methods, Vol 11
248
C3€I+202Me,hexane mninocyclau: I , rt
Youshko, M.I.; van Rantwijk, F.;
6
Section 82
-
Tctrultd-on Asyninz., 2001, 12, 3267.
-6
98% IICOzN , 100°C , 3 h
72%
N€Iz N I ICI10 Chakrnharty. M.; Khasnohis, S.; IIaiigaya, Y.; Konda,Y. Syntli. Cominun., 2000, 30, 187.
/ '
II
iiuciuwaves , 10 inin
kl
\/
I .
3
:
0 .I? Satti, .; N.K.; Suii, K.A. Synth.
,c
Feroci, M.;
N-
i-Pr
2000, 30, 3709.
-
2. coz 3. EtI
Inesl.;Rossi, I..
84%
NEt,' (via electiulysis)
1.
C6WIlNHZ
Coniiiiicn.,
I
C$iiNHCOZEt
-c
Tcrruliedron Lett., 2000, 41, 963.
AcZO , 120"C, BF,*OEtZ
80%
N-Ac
14 h
76%
P.K;Kuinar, K.A.; Duddu, R.; ; Dai, R.; Das, K.K.; Gum, X.-P.; Sun, J.; . . Trlvedl.; Gilardi, R.D. J. Orx. C h ~ n .2000, , 65, 1207.
bIlph
Br
Br>drph
TMSO
Bandini, E.; Favi, G.; Martelli, G.;
heat, toluene overnight
##
40%
0
. Pieisanti, G. Org. Lett., 20U0, 2, 1077.
Section 82
aa,
249
Anides from Amines
0
2. -Br
N
In,DMF,16h
75% (30:70)
CO2Ph
Lab. T.-P.; Lye, P.-L.; Wang, R.-B .; Sim, K.-Y. Tetruherlrnn tctt., 2000, 41, 7779. 1.5g HCO2NH2
-
PhNHCHO 96% MLCN , E t l u x , I l h Reddy, P.G.; Kuinm, G.D.K.; Baskaran. S. Tetruh~clronk t t . , 2000, 41, 9149. PhNH,
I N
1. BuLi, THF, -45°C 2. 1 atin C O , -45°C + -30°C
-
L-
3. sutd aq NH,C1 -30°C 20°C
/
I
84%
Me0
Me 0 Iwamoto, K.; Chatani, N.; Murai. S. J. 01-8.Chern., 2000, 65,7044. ,CY 2% Ru3(CO),2 , 2 atin C O , 20 h
71%
toluene, 160°C 0 -
Kamitani, A.; Chatani, N.; Morimoto, T.; m a i . S, J. Org. Chetlz., 2000,65,930.
i\,,,
(Me0)2C=O9Y - A I ~ O ~
4.
85% Ph wflux, 2 d Ph CHCOZMe Vauthey, I.; Valot, F.; Gozzi, C.; Fache, F.; Jxrnuue. M. Tl,ti-uhedronLett., 2000, 41, 6347. Ph
NH2
C,FS(Me)NC02Ac, THF
Kondo, K.; Sekiinoto, E.; Nukuo, J.;
rt , Soinin
*
NHAc
Ph95%
Tetruhedron, 2000,56,5843.
250
Section 82
Compendium of Organic Synthetic Methods, Vol 11
.
.
Tanirnon. S, ; Kisihata, M. Tetruhedron Lett., 2000, 41, 6785.
KMn04 , DCE ,reflux, 6 h C - P h
B nNEt,CI
co 67%
N-Ph
* MdThtTrlf.; . Stickney, C.A. .I. Heterocyclic CIieni., 2U00,37, 109. 1 .
70%
17) 93%
(83
Davoli.; Prati, F. Hr.terocy1e.T. 2000, -53, 2370. BnCl , K 2 C Q ,596 Bu4NBr, 2 h F MqNC02Bn onium salt , supesciitical CO, 80 at111 , 100°C Yoshidd.; . . Hard, N.; Okuyama, S. Clieni. Coninrim.,2000, 151.
MqNH
1 . DCI , cat DMAP AcCN , heat
\
2. BnOH
H
M:m
also genesates esters fium alcohols Macor.;Cuff, A.; Cornelius, L. T~mdlerlrorzZxrt., I Y Y Y , 40, 2733.
EtzNH
L 7 0 % BnH N
PhNO,, 3 qcr),Se F
Et2N Yang, Y.;
82%
Tctrulwdron Lett., 1999, 40,4845.
NHPh
76%
251
Punides from Esters
Section 83
5% Pd(PPh3)4, Py ,C 0
PhSNEtz
*
8O"C, 10 h PhS Hiraike, II.; Morita, M.; Tanaka, A,; Sugoh, K.; J. Org. C ~ C I IIY99, I., 64, 7305.
m;
1. BuLi, TIIF, 0°C
- rt
PhNHCOEt 2. EtC0,Et , -78°C Ooi. T.; Tayama, E.; Yamada, M.; M a r u o k a . . Y y n l e t t , 1999, 729. PhNNz
a N H
pivalic acid
+ Qo
73%
H
BtC1 , a t PdCl,(Ph&2 C O , MeCN
GW 48%
Cho, C.S.; Jinng, L.H.; Shim. S.C. Synrh. Conimitn., 1999, 2Y, 2695.
(fcl,NEtj,CO a t
95%
Sid,, THF , 1 0 min
C4Me
Ph-N-Du
90%
NEt2
PdCl,(PPh,), , 100°C MeCN, 1 d
Bu
80%
-
Cho, C . S . ; Wu, X.; Jiang, L.H.; & S.C,; Kim, H . K . J. Heterocyclic Cham., 1999, 36, 297.
SECTION 83: AMIDES FROM ESTERS
I
Ph Wang, Y.;
I
Ph
NaN(CHO), , MeCN ,6O"C
J. Org. C h e n ~21101, , 66, 3238.
Ph
Ph
86%
252
Coinpndiuin of Organic Synthetic Methods, Vol 11
Section 83
a t RhCl(PPh3h,3OoC P(OMe)3 ,toluene LiN(SO2Ca4-4-Me)
OMe
* 96%
Cvdns.;Rohinson, J.E.; Moffett, K.K. Org. Lett., 2001, 3, 3269. 4
.
&
O
2
q
o
M
, 1 h, rt M 0.5 BnNH2, MgBr,THF
e
e
:
0
q
N
m
94%
Guo.;Dowdy, E.D.; Li, W.-S.; Polniaszek, R.; DeIaney, E.
n
0
Tetmherlrnn Lctt., 2001. 42, 1843.
NII2
Ph 0
5% RhZ(tpa)d , 2 3 e q M g O , DCE 1.4 eq PhI(0Ac)z ,40"C, 12 h
K'7,
74%
Ph
ois. J, Angew. Chcni. Int. Ed., 2001, 40, 598.
Espino, C.G.; m
cat
Pd(PPh3)4 , EtOH
1 . 2 q (F'hOhP(O)N,
Ph
p,rMK""'
2 eqNi1N3 ,80"C
0
81%
Qhmoto. H.; Nishihara, S.; Yainamoto, S.; IIino, 11.; Nozawa, A.; Suzuki, A. Synlett, 2000, 991.
1. BkSO2Me ,NEt,
PhCOOIl
* PhCONHt-Bu
ggX75%
2. t-BuNIIZ
Bt = henmtliazyl He, H.-Y.; Suzuki, K. J. Orb. Cheni., 2000, 65, 8210.
95% U
O
E
t
L a a 3 7H20 0 EtOIT2 reflux, 5h H U;Bai, Y.; Wang, Z.; Yang, B.; Ma, H. Tetruhedrnn Lett., 2000, 41, 9075.
Section 84
A n d e s from Ethers
Bn 90% Tetrahedron Lett., 2000, 41, 10273.
Chang, M.-Y.; Chang, B.-R.; Tai, H-M.;
P hCOzMe
253
-
PhNII, , mimowaves, t-BuOII
1 inin
PhCONI IP h 83%
Varina. K.S.; Naicker, K.P. Tetrulwdron Lett., 1999,40, 6177.
1. BnNHTs , LRMDS
?
Bn( Ts)N
B n(Ts)N /
2. Rh(PPh3hC1, THF P(0Meh , 3 0 T
c3H7
(3 : 1) 84% Kohinson, J.E.; Nelson, J.D. J. Anr. Chcnz. Sor., 1999, 121,.6761.
SECTION 84:
AMIDES FROM ETHERS, EPOXIDES AND THIOETHERS
Ph-N=CkO,
3% I’d(I’Ph,),
Ph
TIIF, rt Larksarp, C.; Alper. 11. J. Org. Cherrr., 1999,64, 4152.
1 . p-TolS02NH2 ,dioxane KzCO3 ,catTEBA
57% 0
c:613134 2. TsCI , Py , DCM N-TS 3. KzCO,, MeCN Alhanese. D.; I-andini, D.; Penso, M.; Petricci, S. Ittruhedron, 1999, 55, 6387.
c6H1”o
91%
Section 85
Compendium of Organic Synthetic Methods, Vol 11
254
SECTION 85: AMIDES FROM HALIDES AND SULFONATES HZNCHO , DMAP , 120°C 10% PdClZ(PPh3h , 18 h * F3C@ dioxaie , autoclave , 5 har CO Schnyder, A.; Beller, M.; Mehltretter, G.; Nsenda, T.; Studer, M.; J . Org. Clierri., 2001, 66, 4311. NHzN€IBoc. 1% CUI 10% 1.10-phenanthroline
C S ~ C ODMF ~ , ,80T Wolter, M.; Klapars, A,; B u c h w' u Org. k t t . . 2001, 3, 3x03.
YBoc
\
N €12
97%
TBSO-%
TBso \,&'QC) N
C
e
B
! /
r
H
PdZ(hda), , xantphos ,3.5h Cs&03 ,dioxane , 105°C*
"0 \ /
Yin, J.; Ph-C I I=NP h
OTf
*
0
95%
BzNIIl, 1.4 CSZCO~,16 h5 xmtphos/cat Pd2(dha)3 dic~xilne,100°C
t - B u O N H f 3 z
\ /
94%
Org. Lett., 2000, 2, 1101. BnBr,BNAH,hv,4h
*
c
Nc+P
Browning, R.G.; Mahmud, H.; Badarinarayana, V.; Lpvelv. C.J. Tetruliedron Lc.tt., 2001, 42, 7155. t -B
NH,
71%
w.A.F,
Ph-N
*
Ph-I
\ 1
Ph
87%
/ph
VN+fi
BNAH = 1-henzyl- 1,4-dihydronicatinaniide Jin, M.; Zhang, D.; Ynng. L.; I-ium. Y.; Tetrulierlron Lett., 2000, 41, 7357. p-TsNII,, KzC03
I O*Et
Bunce.; Allison, J.C. Synth.
*
DMF Cnnrrrrrtn., 1999, 29, 2175.
62%
'rs
COZEt
Section 87
255
Anides from Ketones
SECTION 86: AMIDES FROM HYDRIDES
dN(
NIICOzEt
M
L
n
W
88%
, ddv. . J&; Suhha Reddy, B.V.; Kumar, G.M.; Madan, C . Synlett, 2001, 1781. TBDM S Q.
TBDMSQ
%
Cat RuOz, N d O 4
I B oc
COzMe
aq EtOAc
*A N
0
C0,Me
I
>95%
Boc Schmitt, A.C.; Jiang, W . Tetruliedron Lett., 2001, 42, 5335.
;-
PhI(OAc), , T s N H ~
PhA
!luorinatud Mn porphyrin
NIWs
- A Ph
X 1% (S8% conversion) Yu, X.-Q.; Huang, J . 4 ; Zhou, X.-G.; Che. C.-& Org. Ixtt., 2000, 2, 2233.
0
2% Ru-umine minplex
PhI=NTs
90% (57% conversion) Au, S.-M.; Iiuang, 1.-S.; Che. C.-hd; Yu, W.-Y. J. Org. Cliern., 2000, 65, 7858.
SECTION 87: AMIDES FROM KETONES /Ts
TsNIiz ,0.5 T i Q , 2 erl NEt3
P 1P h1'
-
DCE, reflux , 5 h
Ram.;Khan, A.A. Syrtth. Conwiitn., 2001. 31, 841.
83% Ph
Compendium of Organic Synthetic Methods, Vol 11
256
IIzN
K
WTS ""K""
,PhSOzNa*HZO
NH,
70%
~
HCOOH ,rt , 6 d
e 0
u; Wright, D.M.J. Aust. J. Chcnz., 2000, 53,73.
-
S
B n N 3 , TiCh , DCM 0°C
Section 87
t
rt
88%
Desai, P.; Schildknegt, K.; Agrios, K.A.; Mossman, C.; Milligan, G.L.; ,&hLL J. Ant. Cheni. Soc., 2000, 122, 7226.
1. LiCHzNMeBoc ,-7XT 2. MeOTf, -78°C 3 . satd NaHCO, , -78°C + i t 4. TFA , CHZClz 5.1SS-160"C
53x75%
J. 01-8.Ch.enz..1999, 64, 4042.
Zhang, S.;
OMvIe
<)I% 1.
M -e
0
PI,-
2. KOH -82°C
N3 -+
98%
Furness, K.; AuhC. J. Org. Lett., ZYYY, I , 405.
ph)Fc=u Ph
Ts'
NwC02Et
w
It
Ts , 5 inin
cp2co+co(co),hcnwtii fl uoride
*
85%
EtOzC Ph Wack, H.; Drury III, W.J.; Taggi, A.E.; Femaris, D.; h c t k a. T, Org. Lett., 1999, 1, 1985.
Section 88
257
h i d e s from Nitriles
Me Furness, K.; Auli&. .I. Org. Lett.. ZYYY, I, 495.
SECTION 88: AMIDES FROM NITRILES
Ph-CN
1. H,PO,,St-, M a 1 1 , I120 i t , ovenlight
-
50%
L-
2 . 4 K2CO3 Ph Kamiiiski, R.; Glass. R.S.: Skowroiiska._B Syntlwsis, 2001, 1308. NaBO3 , 4 HZO , X I EtO€I
PhCN
miiwwaves , 2 min
*
I’h
NH2
85 %
Sharifi, A,; Mohsenzadeh, F.; Mojtahedi, M.M.; Saidi. M.R.; Balalaie, S. Synth. Coniinun., 2001, 3 1 , 431.
MLCN
C3H7NH2 , H 2 0 , D IV E , 1 d 0.1%Pt(II)-phosphine oxide complex
57%
AcN€IC,I-17
e
160°C Cohley, C.J.; van den Ileuvel, M.; Ahhadi. A.: de Vries. J.G. Tetruliedmn Lett., 2000, 41, 2467. PhCH,CN
A c 2 0 , NaBHdNiCI?
PhCH2NIIAc
i
Caddick. S.; deK. Haynes, A.K.; Judd, D.B.; Williams, M.R.V. Tetruhedron Lc)tt., 2000, 41, 35 13. Ph-CN
4 NaOII , PEG-400
microwaves, 45 sec Bendale, P.M.;
Synth.
-
Coillnrurl., 2000,
94%
83%
P11
30, 1713.
NHZ
Coinpendiuin of Organic Synthetic Methods, Vol 11
258
Section 89
SECTION 89: AMIDES FROM ALKENES
A
A’Ts
p-Tol-SO2N(Br)Na15% CuClz
microw ilves
Ph
Chdndd.; . . Vyas, R.;
w.
PhkNTs, 1 0 %TP*Nil, ~ 10% CIuCl
5
Ph
k
*
MtCN , i t , 12 h
TP = tris- (3,5-dilne thylpyrazoyl)h o n k Czopp, M. Org. L.ett., 2001, 3, 1423.
;.T.s-
81%
Ph A.V. J. Org. Cherii.,2001, 66, 30.
2Ts 84%
Ph
H2NCbS
* PhI=O, 10% Cu(MeCN),PFG p h q N MS 3 A , MeCN 78% Dauhen.; Sani&re,L.; Tarrade, A.; Dodd. &.& J. Am. Cheni. Soc., 2001, 123, 7707.
/T”
PhkNTS, C U ( M ~ C N ) , C ~ O ~
A \
Ph
chiral binuphthyl-imine ligand DCM , 20“C, 4 h
N
L-
hllllll~~~(J
92% (22% e e , S)
Shi.;Wang, C.-J.; Chan, A.S.C. T e t r u h d m Asyinin., 2001, 12, 3105.
% n
COZEt
NsONI-ICD$t, CaO , DCM rt ,30rnin
. . ~orreaie,A,; ~ellucanl.L... -r . ~ioravantl.;
Jeon, 11.4.;w e n .
COZEt 91%
NICO,Et Synthesis, 2001, 1975.
aCheni. Coriimin., 2001, 235.
Section 90
Amides from Misc.
1. NaOIi , uwthane , ROII I$[OSO~(OH),] , (DHQD),PHAL > \
1,3~ichloio-SS~imethylhydaitoin , €IzO Ph 2.NaOH
259
phHHPh +
HNYo 0
0
(2 1) 65% 88% t?e 73% ee . . . N . S . ; Sidler, D.R.; Solnewilk, K.B.; Weissinan, S.A.; Larsen, R.D.; Reider, P.J. or#. Lett., 2000, 2, 2x21. nitiido M n - d e n cuinplex O.SPY, 1 . 2 T s 2 0 , D C M
N-Ts
*
Py-N-oxide , 0°C ,30 inin
82%
Nishimura, M.; Minakata, S.; Thongchant, S.; Ryu, I.; Tetruhedron Ixtt.. 2000, 41, 7080. /Ts
chloramine-T , MtCN
A
Ph
lO%€'y-IIBr3, 25°C
Ali, S.I.; Nikal.je, M.D.; &dalai.
Ph 4. Org. Lett., 19Y9, 1, 705.
1. PN=NSO,CII2CI-I,TMS, QOTf MeCN , MS 4A
\ - hP
-
'L
2.4eqTASF,rt
AN"
* Ph
68~62%
Dauben. P.; Dodd. R.H. J. Org. C ~ I C W Z9Y9, ~ . , 64, 5304.
SECTION YO:
"%
AMIDES FROM MISCELLANEOUS COMPOUNDS
4, 0
Linder, M.R.; Podlech. .I,
erg. .?At.,
2001, 3, 1849.
54%
Coinpiidiuin of Organic Synthetic Methods, Vol 11
260
0
Section 90
c;".
h v , MeCN, 18 h
0
Bourguet, E.; Baneres, J.-L.; Girard. .I.-P.; Parello, J.; Vidal, J.-P.; Lusinchi, X.; Declercq, J.-P. Org. L..ett., 2001, 3, 3067.
a
/OH
112 , ALOEt , NiBrzEt
w
x
80% (98% ee)
P d K , toluene, 60°C ,Sd Ph Cundulu unrurtiru lipase B Choi, Y.K.; Kim, M.J.; Ahn, Y.; .Kim. M . 4 . Or-g. Lett., 200Z, 3, 4099. Ph
N--011
r
Peng, J.; I)enF.
Ph Ocal, N.;
Go
BuPyBlj, , PC15, 80°C
Py = pyridiniuin
*
99%
r Tetruherlron IErt., 2001, 42, 403.
N HZ
0
NaOMe , MeOH , Rose hengal
hv , 0 2 Tetrulwdr-on Lztt., 2001, 42, 4765.
N-oH*lK1
A
* Ph
neat, 10S"C, 8 h
Ph Ph = Ph NHPh Chandrasekhiir. S . ; Gopulaiah, K. Tetr-uhodr-onk r t . , 2001, 42, 8123
0
74%
9G%
FeCb , solvent free
N-OH 80"C, 3 h
Khodaei. M.M.; Meyhodi, F A . ; Rezai, N.; Salehi. P. Synth. Conitnun., 2001, 31, 2047.
mSnBu3 PhI=NTs , Cu(0'I'f)Z
MLCN , it D.Y.; Kim, 11,s.; Choi, Y.J.; Mang, J.Y.; Lee, K. Syrith. Conitnun., 2001, 31, 2463.
261
Amides from Misc.
Section 90
PhNO,
-
AczO , I n , InCl?
ClICl, , 2 0 h
Pt1N(oAc)2
(+ 13%F'hNHAc)
81% Kim, B.H.; Cheong, J.W.; Ilan, R.; Jun, Y.M.; Baik, W.; Lee, B.M. Synth. Comtnr~n.,200Z. 31, 3577.
2.5% [RhCl(cod];, , 25% TFA 15% P(o-TolX ,DCM , i-eflux
N-oll
II
A Et
3
Ph
Arisawa, M.; w
0
II
'
P 11/"\ NHEt 29%
7X%
h i. & Or#. Lett., 2001, 3 , 31 1 .
c
II
+
PhI-IN/\at
11
0
[bmiin] PF6 , PzOs
N -01I
9S%
7S"C, 16 11 ionic liquid inediuin
Ken.;Zueva, L.D.; Ou, X. Tetrulierlron
Lctt., 2001, 42, X441.
"-
Yang, El.; Jurkauskas, V.; Mackintosh, N.; Mogrenn, T.; Stephenson, C.R.J.; Foster, K.; Brown, W.; Roberts, E. Cun.J. Clieiii., 2000, 78, 800. Fw"I14Cl, McOII, 15 min ultrasound, ClN),Et N1
-
NHCOzEt
90% (65% in 12 h without sonication Narsihinulu, Ch. Tctruherlron Lett., 2000, 41, 7969.
m; ,. r
0
BuMgCl, TIIF
1
lC1 '
B u 72% 5 % NiCI2(PPh3), EtzN 2h Imnouchcux, I>.; Kouden. J,; I,asne, M.-C. Teti-ulterlron Lett., 2000. 41, 9997. EtzN
N OSOZEt
A
I'h Anilkumar, K.;
Ph
BIi3.OF,t,, DC'M , 2S"C, 6 h
1
Ph Tctrr~hr~droii Ixtt., 2000, 41, 5427
N HPh
98%
Compendium of Organic Synthetic Methods, Vol 11
262
Section 90
TFA , toluene , 110°C Me Me Cordero.;Pisaneschi, F.; Goti, A.; Ollivier, J.; Salnun, J.; Brandi. A. J. Ant. Clierri. Soc., 2000, 122, 8077. Me
BuLi , -78°C
BocN( L i t S O 2Ph Demhech, P.; Seconi, G.; R&&JL
+
0°C
Ts
N-
N-Ts
Me
BuNHBoc
t
71%
Chem. Ew. J., 2000, 6, 1281.
Zn , ALOH
t
0
92%
B 11 Bn Merino. P.; Anoro, S.;Merchan, F.; Tkjero, T. Heterocycles, 2000, 53, 861.
T s / N W
C4Et
PhCH=C=O , toluene, 5 h
(99: 1 cis:?rans) 10% chiral amine , Proton Sponge -78°C- 25°C Ph Taggi, A.E.; Hafez, A.M.; Wack, H.; Young, B.; Drury 111, W.J.; &&J J. Am. Cliem. Soc., 2000, 122, 7831. B o q O , poly~i~ethylhydrosaoxane PhCII=N-011
PhCHlNH Boc Pd-C, EtOH , heat ChdndrdsLkhar.; , . ,, Reddy, M.V.; Chandraiah, L. Synlett, 2000, 1351.
CO2Me i-Pr
/
In , A@, AcOH THF
*
%
i-Pr
N -OH IIai-rison, J.R.; Moody, C.J.; Pitts, M.R. Synlctt, 2000, 1601.
85%
COzMe
NHAc
BiC1, , 8 min 90% iniuowaves N HPh Ph Ph Thakur, A.J.; Boruah, A.; Prajapati, D.; Sandhu. J.S. Synth. Contmltn., 2000, 30, 2105.
85%
Section 90A
Protection of Ainidcs
263
* A
1 . TEAPC , MeCN-TEAP , rt , 1 h 2 . 5 eqTsCl, 25°C , 10 h
"'"\p" Ph
"g
TEAPC = (Et,N), peroxydicartlonate
86% Feroci. M.; biesi. A,; Mucciante, V.; Rossi, L. Tetruherlron Lett., I Y Y Y , 40, 6059.
-
SiOz , microwaves, 140°C
PhCl I=NOI I
hupy.
Ph
PhCONH2
>
quant
1 inin
A; Rkgnier, S . Tctruh~cironLett., 1999, 40, 6221.
Ph
1. PMeq. PMe,, TIIF, 12 2. Bn02CUl, rt
N3
97%
Ph
tZT1Zd.;IJrpi, F.;
Tetruhedmn Lctt., I Y Y 9 , 40, 7.515.
M?SiCl, A q O , heat, 10inin PhN3 Barua, A.; Bez, G.; w a . N.C., Synlctt, I Y Y 9 , 553.
PhNHAc
90%
CF3 1. BuMgCl , cat CkCN-2 LiCl HMPA-THF , 3 0 min 2. II3O+ 3 . P h C K l , NEt,
F,C Tsutsui, 11.; Ichikawa, T.;
SECTION 90A:
BocHN,
S
,
t
Bull. Clie~n.Soc. Jpn., I Y Y Y , 72, 1869
PROTECTION OF AMIDES
BnBr ,Bu3P 1,1'-(~odicai.honyl)ipiperidine
S
0 2
Winum, .I.-Y.; Barragan, V.; w r o .
,Rda
Bn BocN,I
02
J.-L. Tetruherlron Lett., 2001, 42, 601.
86%
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 7 PREPARATION OF AMINES
SECTION 91: AMINES FROM ALKYNES
GH13
-
PhNH2, PCy3 , toluene
*
1
79%
l.S%[Rh(cod)J BF, C6H13 Hartung, C.G.; Tillack, A.; Trauthwein, 14.; Beller. M. J. Org. Clzein., 2001, 66, 6339.
f-(
100 psi NH3
OMe
100"C,14h
82%
N Hetrde. V.B,; Renga. J.M.; Owen, J.M.Tetrahedron Lett., 2001, 42, 1847.
Et
=
Et
Et
1. PhNII2,3% Cp2TiMe2, toluene inicmwaves , 3 h
N I-IW
2.H2,5~PPd/C,THF,2S°C,3d * 54%
Bytschkov, I.; Dove. S , Eur. J . Org. Clz~in.,2001, 4411.
Ph
Z
Ph
1. Ph2CHN2 , 3 % CpzTiMq , 110°C 2.112 , P d C , THF, 25°C , 3 d PhJ
Ha& E.; Sieheneicher, H.; Dove. S. Org. Lett., 2000, 2, 1935. P h = P h
PhNH2 , 1 % Cp2TiMe2 C,D, , 90°C
Ph Haak, E.; Bytschkov, I.; Dove. S. Angew. C l i m . Int. Ed., 1999, 3S, 3389.
67%
Ph
52%
Section 94
Amines from Aldehydes
265
SECTION 92: AMINES FROM ACID DERIVATIVES NO ADDITIONAL EXAMPLES
SECTION 93: AMINES FROM ALCOHOLS AND THIOLS
PhNCO
o\
*
69%
N NHF'h Huang, T.-B.; Voronkov, M.V. J. Org. Chem., 2002, 66, 1043.
;-
1. (EtO)2P(0)NHC0,t-Bu1D U D TPP , TIIF,It , 2 h
B uOI I
*
76%
BuNII3' OTS-
2. TsOII , 1120 , EtOH , refhx Klepacz, A.; Z w i w u Synth. Contiiriin.,2002, 31, 16x3. 1. NH,CO,Ph ,' P A
Laurent, M.;
*
2. IiOH , MLCN , H 2 0 , 50"C, 3h
01I s
PhCI120H
.Gph
80~95%
NH2
Synrlwsis, 2 0 0 0 , 667.
-
1. NaN3 ,CCId-DMF
e
Ph--NHz
95%
2. > 2 PPh3 IWdy, G.V&; Rao, G.V.; Subramanyam, R.V.K.; Synth. Comnzun., 2 0 0 0 , 30, 2233.
SECTION 94: AMINES FROM ALDEHYDES
CHO
Bn
1 . p-anisdine , I X M , MS 4A 2. TMSI, BuLi , TIIF
-78°C-
*
It
NBn2
PMP =p-niethoxyphenyl Reetz, M.T.; Lee. W.K, Org. Lett., 2001, 3, 3119.
Bn (4
1) 88%
Section 94
Coinpendium of Organic Synthetic Methods, Vol 11
266
OH
Cl
K2CO3, 1 h cuso4 Sharehi.;Sarvari, M.H. Synlett, 2001, 9 9 . piperidine, PhSiH3
1) quant
(0 (1
0 ) quant
Ma*ND
THF 0.02,Brtu,~16S h! S ~ C ~
70%
Xiao, W. Org. Lett., 2001, 3, 1745.
R-;.
BuCHO, Et2Zn ,toluene 10% dipeptide m i n e H2N
10% Z ~ ( O ~ - P ~ ) , = I I O ~ -Bu P~
OMe
H
69% (97% ee)
OMe
Porter, J.R.; Traverse, J.F.; Eovevda. A.11.: Snapner, M.L. J. Am. Chern. Soc., 2001, 123, 10409. I12NCH2C02Et, 2eq NaOEt EtOH , M@4
,reflux, 4 h
Meziane, M.A.A.; Royer, S.; Bazureau. J.P. Tctruhedron Lett., 2001, 42, 1017.
PhCH0,HNMe2 5MLiC104/ether
.a .l . dl.; S Azizi, N.; Nairni-.Tarnal, M.R. TetruAerfrorr Zxtt., 2001, 42, 8111.
70%
Section 94
267
Amiiies from Aldehydes
-
0 . 2 q T i c 4 , Et2NSiHMe, , 3 6 h
PhCHO
CH,CI2, 0°C rt Miura, K.; Ootsuka, K.; Suda, S.; Nishikori, H.; PhCHO
PhCHzNEtz
t
-
‘
1. T i ( 0 i - F ~ MezNH, )~~ MeOH ,rt 2. NaBHj , rt Synrh. Cnmniun., 2000, 30, 2001.
90%
Synlett, 2001, 1617. PhCI12NMe2
ClH*H2N
Y=
NHyCo
*
Hz , 2 0 %Pd(OIl)z/C EtON ,rt
Y
93%
WY.; Sercel, A.D.; Johnson, D.R.; Colhry, N.L.; Sun, K.-L.; Roth, B.D. Tetmhedron Lttt., 2000, 41, 8225. PhCIIO
polymethylhydrosiloxane-Ti(Oi-Pr)4
-
M BnpH
90%
B nNH2 , TH F , 5 h Chandrasekhar. S.; Keddy, Ch.R.; Ahmed, M. Synlett, 2000, 1655. ~ C I - 1 0
*
toluene, ntflux NII2 6M HC1 Matsupi.;Tahussa, F.; Minamikawa, 1.-i. Tetruhedl-on Lett., 2000, 41, 8523.
PhCIIO
IJ2’O ,TIIF , 0°C
*
IIZN Suwa, T.; Sugiyama, E.; Shihata, I.; Baha. A Synthesis, 2000, 789. BuNIIz, NiC126 IIzO/MeOI-I
Me
+ ph= )lc= -J
BuzSnCIH--IIMPA, 1 h
* P hCIi2NHBu NaBH, ,rt Saxena, I.; Borah, R.; Sarma. J.C. J. Cherii. Soc., Perkin l’runs. I , 2000, 503. PhCHO
61%
99%
80%
268
Section 96
Compendium of Organic Synthetic Methods, Vol 11
BnONHz , BEt, , DCM ,20°C
P hCHO
BF,*OEt,, MgSO,, 1 d
Miyahe, H.; Yarnakawa, K.; Yoshioka, N.; fiaito.
CHO
NHOBn
t
AEt
Ph
83%
T.Tetruheciron, 1999, 55, 11209.
1. MqN-SiMe, , LiClO,/ether 2. MqPhSiCl , it
Naimi-Jamal, M.R.; Mojtahedi, M.M.; Ipaktschi, .I.; J. Chem. Soc., Perkin Truns. 1, 1999, 3709. Related Methods: Section 102 (Amines from Ketones)
SECTION 95:
AMINES FROM ALKYLS, METHYLENES AND ARYLS NO ADDITIONAL EXAMPLES
SECTION 96: AMINES FROM AMIDES
5
AlCi,, PhH
0
w u p a w a . Y.; Aoki, Y.;Sakamoto, T. .I. Org. Chein., 2001, 66, 8612.
1. MeLi , DME, -78°C 2. TMSOTf ,-78°C 3. t-BuLi , ether, -20°C
-+
25°C
Ahn, Y.; Cardenas, G.I.; Yang, J.; Rolno. D. Org. Lett., 2001, 3, 7511.
58%
Section 96
Amines fmrn Anides
269
1% R ~ ( C O ) ,,,5 % Et,Nrr 96%
toluene , lOO"C, 16 h 3.5 eq HSiEt3 Igarashi, M.; Fuchikami. T. Tetruhedron Lett., 2001, 42, 1945.
Q
1. MqSiCl
II
0
2. PhMgBr
90%
Ph
Coindet, C.; Comel, A.; Kirsch. G. Tetruherlron L.ett., 2001, 42, 6101. PhNIISOZ(2-pyl-idyl)
10 q Mg , MLOII , 0°C
+
PhNH,
86%
3h Pak.; Litn, D.S.Synrlz. Cnnimun., 2001, 31, 2209.
Li, Z.;
a M
-s,rar
0
It
YmF N
H
, 5 min
95%
Tetrulzerlron Lett., 2001, 42, 8507.
Bubnov.;I'astukhov,
F.V.; Yampolsky, I.V.; Ignatenko, A.V Eur. .I Org. . Chcwi., 2000, 1503.
1. t-BuLi, ether, -78°C 2. LiAII-14,ether, reflux *
Jones.; Storey, J.M.D. .I. Clwni. Snc., Prrkin Truns. I , 2000, 769. , aq NaOH , 80°C mcl +
(CH,=CHCH,),N
56%
NH Z 40 h H 2N SdLhmVdld.; ,. . . Winsor, D.L.; Mnskos, K.; GI-imm, C.; Ilarned, 0.;Vigo, T.L.; Bertoniere, N.R. J . Org. Cheni., 2000, 65, 9234.
210
Coinpendiuin of Organic Synthetic Methods, Vol 11
a H N
Section 9 6
l.B(C€I2CI-I=CH2)3,TIIF, 65°C , 2 h 2. Mt0I-l 90%
3.qNaOII
&ov. Y u . ~ Klimnkina, ; E.V.; Zhun, I.V.; Pastukhov, F.V.; Yampolsky, I.V. Pure Appl. Chmi., 2000, 72, 1641. Ph/\""h
TMSCl , N d , MtCN
Phf i N O f i I 88% I b2Ph heat, 3-4 h H Sahitha. G.; Reddy, B.V.S.; Abraham, S.; Yadav, J.S. Tetrukeclron Lett., 1999,40,1569.
I
2.1
9-BBN, TIIF
C - B n
t
6 N - B .
96%
reflux, 1 h
Collins, C.J.; Lanz, M.; Singaram. B. Tc,truheclron Lett., Z999,40, 3673.
01'13s
b N\
1. Na naphthalenide , DME , -78°C 2. HzO
-
Ts S.C.; Seth, P.P. Tetruhcclron Lett., Z999,40,61x1.
-.
O G
N\
89%
H
LiI13B*NMe2,THF, 65"C, 2 h t
86%
&-Bn Flaniken, J.M.; Collins, C.J.; I.anz, MM.; Sinearam. B. Org. Left., Z999,1, 799 BII3OTHF , THF, heat 0a
N
I
0
* cI )
Tr Akula, M.R.; Xahalka. G.W. Org. Prep. Proceed. Int., 1999,31,214. Related Methods: Section 1OSA (Protection of Amines)
N
Tr
81%
Section 97
h n i n e s from &nines
27 1
cN-p
SECTION 97: AMINES FROM AMINES PhCl , 3
t-BuOK
*
92%
Beller. M,;Breindl, C.; Riernieier, T.H.; Tillack, A. J. Org. Chent., 2001, 66, 1403. Ph
PhB(OH), , H 2 0 , r t , O2 cat [Cu(OI-I)(t~nedu)]~Cl~ overnight J.P.; Zhong, M.; Zeng, L.; Costanzo, S. J. Org. Ch.eriz.,2001, 66, 528. 1 . r-BuLi , ether ,-78°C
s
~
30 min
M 2. PhCH2Br ~ ~
Q-Ph i2e2
99% Itiuni, K.; Kame, T.; Mitsudo, K.; Nokami, T.; Yoshida. J.-i. J. Org. Chmn., 2001, 66, 3970.
1. L i , DTBB I'h a-"-
* a N P
2. HZO
Yus. M.: Soler, T.; Fouhelo. F. .I. Org. Cliern., 2001, 66, 6207.
K
N-PMP
Pd(OzCCF3),, R-BINAP , rt
& F7 C
C02Et
100 atin 112 , CF7CI120H , 1 d
Ahe, H.; m.€I... IJnev. & . Org. L,ett., 2001, 3, 313. NHBn+ B F456p;:DCM,it
(c
h
>99%
H
& F,,C
>99% (88% ee ,R )
2% CpRu(SS-Chiraphos)II
/
/
Magee, M.P.; Norton. .I.& J. Am. C ~ W JSnr., L 2001, 123, 1778.
/
/
90% (60% ee)
212
Compendium of Organic Synthetic Methods, Vol 11
--Q
Ph
10%peptidic ligand 10%Zr(0i-Pr),
0Me
Section 97
Et :
Ph
Et,Zn, i-pIOIJ toluene
I
84% (93% ee)
Porter, J.R.; Traverse, J.F.; J. Am. Chem. SOC., 2001, 123, 984.
2.5%PCy3,6O0
THF ,20h .ran, K.L.;
70%
; Ellman, J.A. J. Am. Clicm. Soc. 2001, 123, 2685.
Li I THF ,-20°C , 4 h 2. 1. ri,o
-
"
O
A
r
n
>9J %
AzzLnd.; . . Pilo, L.; Piras, E. Tetruherlroiz Lett., 2001, 42, 129.
b;
b
& H
1% CuCl, 10% chiral diamine 2.1 K3PO4, 110°C , Id dioxane
' J. Ani. Chern. SOC.,2001, 123, 7121. Klapars, A.; Antilla, J.C.; Huang, X.; Buchwald. S.L,
pyirolidine , EtOII , wflux 2% flr(cod)Cl]z, 8% P(OPhh 3h Ph
(96
Takeuchl.; IJe, N.; Tanahe, K.; Yarnashita, K.; Shiga. N. J. Am. Cherii. Sor., 2001, 123, 9525.
:
4) 95%
Amines from Atnines
Section 97
PhOTf Pd(OAc), , dppf
X
N
273
Q
n
h
DABCO, DMSO 80°C
KuJ..; Marcoux, J.-F.; Davies, I.W.; Reider, P.J. Tetruhedron Left., 2001, 42,
, NIIB z
JL
NHN I IBz
sic13
DMF, 0°C , 18 h
Ph
159.
*
ph+ 79% (1:99 syn:unfi) Hirahayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi, S . J. Am. Chem. Soc., 2001, 123, 9493.
EtI , InC13 , Mn2(CO),,
A
Bn
r-r Et Friestad, G.K.; Qin, J. J. Am.
A
/
se
hv
s,
Et
Et
Clieiii.
Snc., 2001, 123, 9922.
o 0 y q
MeMgBr, toluene, rt
.
~
cat Sc(OTf)3,3 h
P I1 Saito, S.; Hatanaka, K.; Ph
90%
Synlett, 2001, 1859
C
N-CCIK)
*
Ph Iwasaki, I:.; Onomura, 0.;Mishhna, K.; Kanernatsu, T.; Maki, T.; Tetrulierlrnn Lett., 2001, 42, 2525.
Ph Biscoe, M.R.; Fry. A.J. Tetrulirdron Ixtt.. 2001, 42, 2159.
)lr
Ph
Ck$iH, CH2CI,
Ph
79%
274
Compendium of Organic Synthetic Methods, Vol 11
cNa
Section 97
a t Ru,(CO),~,CO , 21 h
CII,=€H,, i-&OH , 140°C Et
92% (54:46)
Chatani, N.; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.; J . Am. Chern. Snc., 2001, 123, 10935.
Kim, Y.K.;
1
)use. L;Bercaw, J.W. Tetruhedron Lctt., 2001, 42, 2933.
NHi-Pr
1. hv (254 tun)
Likhotvorik, I.T.; Tippmann, E.; Ela
.S. Tetruhedron Lett., 2001, 42, 3049. 1. EtMgBr ,THF ,-78°C
E0,C
/
Niwa, Y.; 'lakayaina, K.; Shunizu. PhNtI,
* p-An-NHEt
2. air, aq KOH , EtOII
M.Tetruhedron Lett., 2001, 42, 5473.
1. ZnEtz , Cu(acac), , EM-hexane
+
i PhNIIEt 2. 10% MCl (9 : 3.10% aq NaON Brides, C.; [Iarnett, J.J.; Doris. E. Tetruhetlron Lett., 2001, 42, 8301.
Chrzanowsk;r.; SokoIowska, 1. Tctruhetlron
91~84%
PhNEt,
1) 95%
77% (32% el?) Asyiniii.,
2001, 12, 1435.
Me
Amines froin Amines
Section 97
PhBr ,cat Pdz(dba)3, DINAP NaOt-Bu , toluene , 80°C , 1 d Tetruheclron, 2001, 57, 2953.
Cai, W.;
(IIOCH2CH2)3N*€ICl, 20 h cat R~€lz(PPh3)4, 180°C SnC12*2HZO , aq dioxane
N Hz Kim, J.II.; Kim, T.-J.;
;-
275
a *
P h I I N q 53%
85%
H
Tetrulzerlron, 2001, 57, 3321
BnCI , CsFXelite , MeCN PF1zNBn 70% Ph2N€I IIayat, S.;Rahman, A.-u.; Choudhary, M.I.; Khan, K.M.; Schumann, W.; paver. E. Tetruheclron, 2001, 57, 9951.
N-OB n
2.5 i-pr
98% (68% ee) Fontalne.;Namane, C.; Meneyrol, .I.; Geslin, M.; Serva, L.; Roussey, E.; Tissandib, S.; Maftouh, M.; Roger, P. Tetruheclron Asyriirii., 2001, 12, 2185.
c
Ph
o
d/N\
,LBF~,MLCN t
ph 88% (85:15 trurnscis) Yadav. J.S.; Reddy, B.V.S.; Madhuri, C.R.; Sahitha, G . Synthesis, 2001, 1065.
€1.
L
Q
b
B
r
1
Pdz(dba)vdppf
NaOt-Bu ,dioxane , 110°C , 6 h
Cheng, J.; Trudell. M.I, Org. Zxtt., 2001, 3, 1371.
66%
Section 91
Compendium of Organic Synthetic Methods, Vol 11
276
PhNII,
-
PhB(OH), , 2,6-lutidine, air
5% Cu(OAck, 10% myiistic acid Antilla, J.C.; Buchwald. S .L. Org. Lett., 200Z, 3, 2017. B'\
A
SmBr,-HMPA, rt
*
Br,
PhNAPh
19%
NII
AMe
>99%
Ph 15 inin Ph Knettle, B.W.; Flowers II, R.A. Orb'. Letr., 2001, 3, 2321. cat L,LnEL(TMS), C'&6,12S°C, 9 h
>95% Org. Lxtt., 2001, 3, 3091.
..
CI 12=C€ICH,ZnBr TIIF, 0°C
-+
rt
Ph
I1 van der Sluis, M.; Dalmolen, .I.; de Lange, B.; Kaptein, 13.; Org. Lett., 2001, 3, 3943.
9
. P.L; Soldevilla,
PhlNH
+ PhI
A,; Sampedro, D.; m u e z .
; Broxterman, Q.B.
Or& Lett., 200Z, 3 , 4087.
10% Cu(neocup)(PPh3)Br
78%
P h,N -Ph t-BuOK , toluene, 110°C , 6 h Gujadhur, R.K.; Bates, C.G.; Venkataraman, D. Org. ZXtt., 2001, 3, 4315. 2. EtI
i-PiO,C
3. aq NI14Cl
-ep'
Cqi-Pr
cozi-pr1. Na , NI13 I-Pr0,C
b h o e . T.J,; McRiner, A.J.; Helliwell, M.; Sheldrake, P. J . Chcm. Soc., Perkin Trans. 1, 2001, 1435.
Et
H
98%
277
Anincs from Anlines
Section 97
PhII , 5 eq NC13, rt , 1 h
NH2
N I IMe
Me r Ohwada, A.; Nara, S.; Sakmoto. T.; J. Chem. SOC.,Perkin Truns. 1, 2001, 3064.
92% .
chiral Zr catalyst, toluene
Ph
013
Gastner, T.; Ishitani, H ; Akiyama, R.; K&ay&LL ' m
B
*
74%(55% ee) Angew. Cheni. Int. Ed., 2001, 40, 1896.
, Yh, I'MSCI
r
l'hvN-Ph TIIF
* R
Synrh. Cotnniitrz., 2001, 3 I , 273.
Su, W.; Li, .I.;
2.5 eq
P hCH= N-P h
Y 7 N HPh
5
%
In , N€IdCl, EtOII
t PhCI12NIIPh icflux, 10 h Banik.; Hackfeld, L.; Becker, F.F. Synth. Contrnun., 2001, 31, 1581.
m
B
r
, SlllIZ
THF, 6 h,O"C
.+
- k NIIPh
P hCH=N-P h rt
a
Ph kim.; IIan, K.; Park, K.J.; Bai, K.H.; Jun, Y.M.; Baik, W. Synth. Comnirtn., 2001, 31, 2297.
00
decalmrane , rt , 3 0 inin 37% IICIIO in MLGI-I
91%
I
tI
Jung, Y.J.; Boe, J.W.; Yoon, C.-O.M.; Yoo, B.W.; yoon. C.M, Synth Contnrun., 2001, 31, 3417. PhNH,
Bu,NBr, cat Ru,(CO),, , dioxane SnC12-2 IIzO , 180°C , 2 0 h
Cho. C.S,; Kim, J.S.; Kim, 1I.S.; Kim, T.-.I.;
95%
t
PhNHBu
Me
(+5%PhNBuz)
68% Syntlz. Conitnun., 2001, 31, 3791.
278
Compendium of Organic Synthetic Methods, Vol 11
N-Ph
A
2 q EtMgCl, THF ,20"C 10%Cp2ZrC1, , 15 h
Ph Gandon, V.; Bertus, P.;
Xh
*
78%
Ph
Eur. J. Org. Cheni., 2001, 3677.
*
II2
, fermcenyl-hinaphthyl complex of I r 40 h
Ph
NHPh
- A Ph
quant (84% ee)
Angew. Chein. Int. Ed., 2001, 40, 3425.
Xiao, D.;
-
Et3NI-I' IICO2-, IICOOI1
PhCH=NP h
Section 97
PhCH,NHPh microwaves, 4 inin Mophaddam.; Khakshoor, 0.;Ghaffarzadeh, M. J. Cheni. Res. (S), 2001, 525.
PhA "
Y
1. &Br
)(
l u
, D M Fl ,hr t
*
N
2. AcOEt , 1N HC1
€I
OH
95% (>99% de)
OH
Yanada.; Kaieda, A.; Takemoto, Y. J. Org. Cheni., 2001, 66, 7516. BnNI-I,
2.5 eq PhCIIO , 4 eq HCOOII
w
micmwaves, 5 inin
B nBHB n 59% (+ 40% Bn3N)
Torchy, S.; Barlvy. D. J . Clwn. Res. (S), 2001, 202.
li(i-Prl3 eSi(i-Pr)3
H
$3 P -
SnC14 , toluene 0°C. MS 4A
O2N
Ncivama.; Suzuki, M.; Kagoshima,
OZN
l11111ll11
#
91%(84:16cis:trms)
13. Heterocycles, 2000, 52, 529.
Section 97
Amines from h n i n e s
N -C,
H7
ITIF, r t , 4 h
279
*
&
Denisenko, A.; Denisenko, S.N.; Arend, M. J. Heteroryclir Cherii., 2000, 37, 1309.
;-
C A N , aq MeCN, rt B n,N -C7I I, + BnNII-C,II, 69% Bull, S.D.; Davies. S.G.; Fenton, G.; Mulvaney, A.W.; Prasad, R.S.; Smith, A.D. J. Chem. Soc., Perkin Truns. I , 2000, 3765.
& AcO.
B uNI 12
Ph
I OAc
-t B uNI1Ph Cu(0Ac)Z , THF, S O T , 14 h I'edorov, A.Yu.; Finet. J.-P. J. Cherii. Soc., Perkin Trans. 1, 2000, 3775. .
MS 4 A ,DMF ,23"C 77% 28 h Salvatore, R.N.; Schmidt, S.E.; Shin, S.I.; Nagle, AS.; Worrell, J.H.; J,lrg, K.W. Tetruhedron Lett., 2000, 41,9705.
N I IBn 'I'MSN3, MLCN O
N
-
B
n
rt , 2 5 h
Chandrasekhar, M.; Sekar, G.; &@, V.K. Tetrulieciron Lett., 2000, 41, 10079.
Xekou Koulotakis, N.P.; I-Iadjiantoniou-Maroulis, C.P.; Tetruhedrori Lztt., 2000, 41, 10209.
64%
66%
280
Compendium of Organic Synthetic Methods, Vol 11
oy
Section 97
-d\” &
N-Ph
[PhSiH, , Ti catalyst, MeOII ,pyiulidine] i-BuNH2 , slow ddition , 60°C
63% (99%ee)
’
IIansen, M.C.; J j u c h w u Org. k t t . . 2000, 2 , 713.
PhI, Pd2(dhah ,THF , 1 d cszc03 biphenyl amino-phosphine
*
PhH N H2N Edmondson, S.D.; Mastracchio, A.; Partnee, E.R. Org. Lett., 2000, 2, 1109. 1 . PhCMO ,Ti(Oi-Pr), 2. vacuum
B t12NH
/
mBr
7
68%
3. ,TIIF,In B n2N Choucair, B.; L h n , 11.; Mir6, M.-A.; Lehreton, C.; Mosset. P, Org. Lett., 2000, 2, 1851.
,,&‘
DDQ , DCM , HzO , ~tt-
,&”
B n2N
BnHN
86%
Hungerhoff, B.; Samanta, S.S.;Roels, 1.; Metz. P, Synlett, 2000, 77.
0”) & H
/
*
80%
Yadav. JS,; Reddy, B.V.S.; Rasheed, M.A.; Kurnar, H.M.S. Synliqt, 2000, 487.
1. ChTi(TADD0L) + BINOL , 6 h 2 a 1 M q S i C N , CH2C12,-40°C mpN13n
2. € 1 2 0
*
NI 1Bn p>
CN
95% conversion 31% ee) Byrne, J.J.; Chavarot, M.; Chavant, P.-Y.; VallCe. Y. Tetralledron Lett., 2000, 41, 873.
Section 97
Amines from Amines
Ph21+BF4-, 10% CuI 2 eq Na,CO,, DCM , rt , 6 h
28 1
-
C N - F ' h
65%
S . - L ; Lee, S.-H.; Ixe,D. Synlett, 2000, 1022.
30% aq H 2 0 2 , acetone
Ph
ph*
0.1% Mn,O(OAc),(TPTN) Bull, S.D.;Davles.;Fenton, G.; Mulvaney, A.W.; Prasad, R.S.; Smith, A.D. Chern. Conirrictn., 2000, 337. 5 % Cp2ZrClz , 'IHF , 6 h 2 q BuMgCl ,22"C
de Armas, .I.Kolis, ; S.P.; Hovevda. A . K J.
hi.
Chern. Soc., 2000, 122, 5977.
1.2.2 eq t-BuLi ,-78°C pentane-ellier 2. (-)-sparkine
*
3. -4O"C, 1.5 h 69% (93:7 er)
Bailey. W.F.; Mealy, M.J. J. Arir. Cltetii. Soc., 2000, 122, 6787. 1. t-BuLi , (-)-sparkine toluene,-90"C ~
\Bn
2. H,O+
\
Bn
85% (87% ee) Gil, G.S.; Groth, LJ.M. J .
h i .
Cherri. Soc., 2000, 122, 6789.
MtCN nicotinilun , Ivflux, dichroimte 1.5 min
H
*Etozc)p COzEt
E t O 2 C m C O 2 E t
Mohaiiunadpoor-Baltol-k, I.: Memarian, I1.R.; Suhhani, S. Synth. Corizniun., 2000, 30, 1661.
;-'-
1
97%
282
Section 97
Coinpendium of Organic Synthetic Methods, Vol 11
p - B r , toluene
2.1 NaOt-B u cat Pdz(dha)3 , 80°C a t aryl phosphine 84%
Etozn J. Org. Chein., 2000, 65, 5327.
Harris, M.C.;
COZEt
H
Mg(HSO,), ,
D C M , r t , 10min
75%
.zolficol. M .A,; Eany-Borazjani, M.; Sadeghi, M.M.; Moha~iunadpoor-Baltork,I.; Memarian, H.R. Synth. Conrniun., 2000, 30, 3919. NaII2P03 , HCHO
; .
C3H7
C3H7
X=CN X = C0,Me Davis.;Durden, D.A. Synth. Cornnilin., 2000, 30, 3353.
*
Bu,N HSO, , (MeO),sO, toluene, q NaOH
N
Ph
chiral his-oxazoline ligand
I
X
Me
90% 83%
pJNHM 98%
NOz
Voskresensky, S.; Mnkosza. M. Syntli. Cominiin., 2000, 30, 3523. 2 eq MeLi , toluene, -75°C
N
-
--
NH-p-Tol Ph 97% (73% ee)
Denmark.;
Stiff, C.M. J. Org. Chen~.,2000, 65, 5875.
Oxone, 8O"C, SiOz , 8 h B u ~ 1.N1 Fields, J.D.; fiopp. P.J. J. Org. Chern., 2000, 65, 5937.
b
Bu~N-OH
98%
Section 97
Amines from Amines
1.
283
-
-a-b
,36"C, 3 h
-)3*
2. aq NaOH €1 H Buhnov. Y.N.; Zhun, I.V.; Klimkina, E.V.; Igantenko, A.V.; Starkova, Z.A. Eur. J. Org. Chern., 2000, 3323. , Pd(OAch, 80°C
-\.
* PhHN PPh3 , Tr(Oi-Pr)4, MS 4,& ySne S.-C7,; Yu, C.-L.; Tsai, Y.-C. Tetruhcdron Lett., 2000, 41, 7097. PhNIl,
t
p . 1 1 2
Ph(0i-Pr Ac),
98%
88%
i-Pr
-
Saito, S.; Kano,T.; Ohyabu, Y.; Yamamoto. H. Synlett., 2000, 1676.
Coldham.I.;Fernhndez, J.-C.; Snowden, D.J. Tetruhedron Lcctt., 1999, 40, 1-propanol , 300°C
80%
1819.
* PhCII2NIIC3H7
*O0/O conversion 77% monoalkylation 5% dialkylation Valot, F.; Fache, F.; Jacquot, R.; Spagnol, M.; Lemaire. M . Tetruhedron Lett., 1999, 40, 3689. PhCHzNHl
y-A 12O3
[lie(CN).jNO]-', MeCN
BuNH~
*
BuZNH
N2 . - Tripani, C. Tctruherlron Lett., Doctorovlch.; Z999, 40, 4635.
'"\=
S i n , I2 , rt , 3 0 nun
N -1'h
some inines gave diiners
Danik.;Zegrocka, 0.;Banik, I.; Hackfeld, L.; Tetruherlr-on Lett., 1999, 40,673 1 .
t
LNH 58% ~
Ph
Section 97
Compendium of Organic Synthetic Methods, Vol 11
284
JfBn
W S i M e 3
c
69%
5
(&3H5PdClh, TBAF, 31 h Ph Ph hexane/THF. 8 h Nakamura, K.; Nakamura, H.: yamamoto. Y. J. Org. Cherlt., ZY99, 64, 2614.
Et
H Amedondo, V.M.; Tian, S.; Md&n&l. . Ph
F.E.. M,lrks.T, . . I J. Am. Chem. Soc., 1999, 121, 3633. 4
4
.
CHiCl2, 40°C , 2 0 h PhJMe ..Kainz, S.; Brinlanann, A,; W r . W.: P f
Ph
-
0.15%1chiral Ir catalyst, H2
N I IBz
xMe
88%
99.7% (83%ee ,R )
Ph u J. Am. Chcni. Soc., Z999, 121, 6421. NHBz
Sic13
96% D M F , r t , 1h
Ph Ph KohavJ,,hl.; .. Hirahayashi, R. J. Am. Chctri. Soc., 1999, 121, 6940.
C5H 11N1l 2
Ph3SiH (Ph2CIl)PhN-Yh(hmpa)4
t
C5H NHSiPh3
61%
. . Kamata, T.; Miura, Y.; Shishido, T.; Takehira, K. J. Org. Chem., 1999, 64, 3891. nakakl.;
Xh
Ph ;-
* P h fiPh N
TiCh ,NEt,
I
90%
Ftl
Srinivas, G.; Bharathi, P. J. 01-8.Cl?em., 29Y9, 64, 4204.
N / Ph
-SiMe3
,5 h
1% D A F , THF, MS 4A
-
93% ph
PhA H Wang, D.-K.; Zhou, Y.-G.;Tang, Y.; &>u. X.-L; Dai, I..-X. J . Org. Chem., Z999, 64, 4233.
Section 97
Amines from Amines
285
1 . Pd(OAc), , r x BINAP , 8 W C NaOt-B u tolUtXlle
2 . Pd(OAc), ,NaOt-Bu, 80°C:
chirlll phosphine toluene
Harris, M.C.; Geis, 0.; Bn, Bn-011
-Ph
1
d d . S L J. Org. Chern., 1999, 64, 6019.
.
TsCl , Py , DMAP
--
k
DCM,rt, 12h
!Jundrasekhar. S.;Mohanty, P.K.; Narikishan, K.; Sasmal, P.K. Org. Lett., 1999, I , 877.
NIIMe
MeIIN
W(C0), , COII2IKzCO3
E M
McCusker, J.E.; Grasso, C.A.; Main, A.D.; WC1wee-W
*
MeNu 48%
erg. h t . , 1999, I , 961.
Tortolani. D .R.;Poss, M A . Orx. L ~ t t . I,Y Y Y , I, 1261.
Nv
I Roesch, K.R.;
PhCXPh, Na2C03,8 h .5% Pd( O A C ),~LiCl DMI' , 100°C Orb'. La., l Y Y 9 , I, 1551.
85%
Compendium of Organic Synthetic Methods, Vol 11
286
1. DDQ , PhH, MS 4,4 L-
2. 0.1N HCl Sampson, P.B.; Bonek. J.F, Org. Lett., 1999, I, 1395. TMSN3, acetone
a
NHCH2Ar
% ,
BuBr , CsOH*H20, 21 h 'Iiz
DMF ,MS 4 A ,23°C
Salvatore, R.N.; Nagle, A S . ; Schmidt, S.E.;
1.5
,AcOH
&GeB3
Ph*N-h
71%
C,H7NH3 C1
5% Crcornplex Ar = 2,4dinitrophenyl Li, Z.; FernSndez, M.; Ja01-6' Iktt., . ZYYY, 1, 1611. ph-
-
+
60"C, 1 h
Ph2C€INHGII,
Section 97
-
Ph-
N3
quant (70% ee)
NHBu
Org. Zxtt., 1999, I, 1893.
*
0.5 BF3eOEt2, MeCN ,0°C Ph Akivama, T.; Iwai, J.; Onuma, Y.; Kagoshima, H. Chcni. Conimun., 1999, 2191.
89% ~-
90%
t
cat MgIr ,TIIF
(91 Alper, P.B.; Meyers, C.; Lerchner, A.; Siegel, D.R.; Carreira. E . N Angcw. Chmi. Int. Ed., 1999, 38, 3186.
Locher, C.; Peerzada, N. J. Clzein. Soc., Perkin Truns. I, I Y Y Y , 179.
1) 55%
92~87~70%
Section 97
Axnines from Amines
287
ZnCI2, microwaves Montmoiillonite K10
143"C,35 min
4 d s k L L ;GuihB-Jampel, E.; Petit,
GO%
A.; Loupy, A. Synth. Coniniun., ZYYY, 2Y, 1 3 4 9 .
2 eq E a r , DMSO , K2C03
PhNI-I,
PhNBt,
It , 6 h
95%
P.M& ; Bhaduri, A.P. Synth. Cnnrniun., 1999, 2Y, 2085.
Srivastava, S.K.; -.
B nBr , K2CO2-Al2O3
N
miaowaves, 5 min
>c) I N
I1
98%
Bn Jasiinghani, H.G.; Khadilkar. B.M. Synth. Contnricn., ZYYY, 2Y, 3603. - -(Si (Me)
;-
.
, . >
I-I-O--)n-
ZnC1, , ether Reddy, M.V.; Chandraiah, L. Synth.
.
Ph,NAPh H Coiirriiun, I Y Y Y , 29,- 3981.
67%
:
cNl>\
Brimhle. M . A . ; Gorsuch, S. Aust. J . Chern., I Y Y Y , 52, 065.
H
[Rh]/BiPhePhos , PhII H2/CY) ,XO"C, 20 h cat
(CH2)y
Bergmann, D.J.; Campi, E.M.; Jackson. W.R.; Patti, A.F. Aust. J. Chenz., 2999, 52, 1131.
C7II 1s CP7
MeHN
1. NCS , toluene ,it , 3 0 min 2. Bu,SnH , AIBN , toluene reflux , 1 h 3.10%)XI KF
Senhoku.;Ilasegawa, €I.; Orito, K.;
D
* Bu
I
59% Me Hetcmcycles, ZYYY, SO, 333.
"#I,#,,
c+,5
Compendium of Organic Synthetic Methods, Vol 11
288
Section 98
REVIEWS : "Amines Via Nucleophilic 1, 2-Addition To Ketimines. Construction Of Nitrogen-Substituted Quaternary Carbon Atoms," StelniL. A.G.: SDero. D .M, Org. Prep. Proceed.. Int., 2000, 32, 205. "Catalytic Enantioselective Addition To Imines," Kohayashi, Sh.; Ishitani, H. Chem. Rev., 1999, 99, 1069.
SECTION 98: AMINES FROM ESTERS 1. LiH,BNMe2, T I I F , 25°C Ph
OMS
--
2.3M I-ICI ,MeOH
Ph
NMez
92% Org. Lett., 2001, 3 , 3915.
Thomas, S.; IIuynh, T.; Enriquez-Rios, V.;
phwPh Phw (C,HT)ZNH, 5% RU atlilyst
I I
I I
t
CHZCI2,20"C , 10 h
OC0,Et
N(C3H7)L 89% (74% ee>
Matsushima, Y.; Onitsuka, K.; Kondo, T.; Mitsudo, T.-a.; J. h i . Cheni. SOC., 2001, 12, 10405. OAc
I
4
Ph
Ph
NIIB n
cat Pdz(dba)3 ,BnNH,
I
S-BINAP, THF, 2 d
Ph
79% (39% ee ,Sx)
Kodama. H.; Taiji, T.; Ohta.; Furukawa, I. Synlert, 2001, 385. CdI,,NIITs, rt
cat TiC14 , 5 h
Ph,>-.
*
CQI,aHN
Ph
Ph
Mahrwald.; Quint, S . Tetruherlron Lett., 2001, 42, 1655.
41%
(C3H7)2NH1 HZO ,25"C cat [l'd(C3H~)C1]2, 20 h OAc
t
tetnphosphine ligand Feuerstein, M.; Laurenti, D.; Doucet. 11... Smte . IliM,Tetruhcdron Lxtt., 2001, 42, 2313.
Amines from Halides
Section 100
289
AMINES FROM ETHERS, EPOXIDES AND THIOETHERS
SECTION 99:
NO ADDITIONAL EXAMPLES
SECTION 100: AMINES FROM HALIDES AND SULFONATES Et2NH , Pd(OAc)?, phosphine ligand
*
Ph- -I
NaOf-Bu , toluene , X0"C J. Or#. Cllerrt., 2001, 66, 2560.
Ah, M.H.; Duchwald.
b /
Ph--NEG Ph,
PhNHMe , 1.5
85%
,Me
NaOt-BU
1% Pd(OAc),, toluene, 80°C polymer- bound phosphine ligaid * 93%
t-Bu
Parrish, C.A.; D u c h w d . 5
J . O r g . C ~ C I I2001, I . , 66, 7820.
t-Bu
Grasa. G.A.; Viciu, M.S.; Huang, .I. Nolan. ; 5*,PL J. Org. Chcni.,2001, 66, 7129.
Ph-Br
1. TMS,NLi , 2% Pd(dha), , Pt-B u3
*
r t , 16h 2. IIC1 Lee, S . ; Jorgensen, M.; m w i e . J.F, Org. . M I . , 20191,3, 2729.
Ph-NH2
98%
92%
Compendium of Organic Synthetic Methods, Vol 11
290
Section 100
1. Ph3SiNH2, toluene .5%Pdz(dbah , 1.3 LiIIMDS
* 6
1.2% =l+PI( 2. H30+
e
c?
piperkline, TI-IF NaI Vt- AnONa
+
10% Ni(0)hipy reflux, 15 min
c1
x0YN-""'
p
0
: (75 Desmarets, C.; Schneider, R.; Fort. Y,Tetruhedron LL,tt., 200Z, 42, 247.
e- , cohabxime , MeOII
Et,NOTs , NaOH, rt Bu 0
Inokuchi.;Kawafuchi, H. Synlctt,
M 98%
pcY3
Huang, X.; Buchwald. S.L. Org. Lett., 2001, 3, 3417.
Bu 0
0
25) 68%
NHOMe
61% (5.6:l)
2001, 421.
Lane.;Zewge, D.; Houpis, I.N.; Volante, R.P. Tetrahedron Lxtt., 200Z, 42, 3251. pyirolicline , NaII , t-BuOH , 3 h PhCl
2V0 Ni(acac>,
*
P h - 0
8% dihydmiindazoline carbene ligand
Gradel, B.; Brenner, E.; Schneider, R.; Fort. Y . Tetruhcdron Lett, 2001, 42, 5689.
96%
Section 100
29 1
Arnines from Halides
pyrrolidine , K 2 C 4 DMSO, ultrasound 15 min
92%
Magdolen, P.; MeEiarovi, M.; US. Tctruhedron, 2001, 57, 4781.
Pd(OAch, BINAP, 18 h
c1 KzCO3, toluene, reflux
Junckers, T.H.M.; Maes, B.U.W.; LemiBre, G.L.F.; r)oinmisse. R. Tctruheciron, 2001, 57, 1021.
L m
NIIB oc
B~
-
, cat CuBr-SMq
DMF , -10°C
H
NHBoc
rt , 14 h
= 51% Hunter, C.; Jackson. R.F.W.; Rami, H.K. J. C h f m Snc., Perkin Truns I , 2001, 1349.
a-
Br , toluene, 3
11 t
cat PdC12 , hisphosphine ligand NaOt-Bu ,80"C
/
97%
%hang, X.-X.; IIarris, M.C.; Sadighi, KJ.P.; Buchwald, S.L. Cun. J. Chent., 2001, 79, 1799. OMe PhNHMe, 0.5%Pdz(clha)3 L-
15%
BINAP, NaOt-Bu ,8O"C tuluene , 29 h Wolfe, J.P.; Buchwnld. S.1,. J. Orx. Clwn., 2000, 65, 1144.
2.5%Pd2(dha)3 , indole toluene, t-BuONa , 100°C biphenyl amino-phosphine 90% Old, 11.W.; IIaiTis, M.C.; Buchwald. S.L. Or-g. Lett., 2000, 2, 1403
292
Compendium of Organic Synthetic Methods, Vol 11
Section 100
A
\p
HN
N
C
O
\ /
C
I
A
,catNi(II)/C
dppf , LiOt-Bu , toluene BuLi ,2.5 h tz. B.H.; Ueda, H. Angew. Chcm. Int. Ed., 2000, 39, 4492.
1. NUN,, MeCN 2. PPh,
PhCH,Br
3. PhCIIO
-
88%
P hCH,N=C HPh
95 %
Van&, P.; Klbn, P. Synth. Comiiiun., 2000, 30, 1503
CI-I0 l w i c N20,, microwaves
. wa . l.; Id Sapra, P.; Dave, B. Synrlt.
mpB
Conintun., 2000, 30, 4479.
DMF PPh3,,10% 110°C Pd(OAc), , 2h *
60%
51%
Kwong, F.Y.; Lai, C.W.; Tian, Y.; Chan. K.S. Tetruhedr-on Lett., 2000, 41, 10285
DME B u ~ N HPd(dba)z, , t-B uONa , rt , 20 h
-
+NBU2
86% Stauffer, S.R.;Lee, S.; Stambuli, J.P.; I-Iauck, S.I.; &&J&JJ- Org. Lett., 2000, 2, 1423.
Suwa, T.; Sugiyama, E.; Shihata, I.; 3 a h a . A. Synlett, 2000, 556. PhNIIMe , t-BuOK dioxane , Pd2(dba)3 Ar'
n Arcl-
N@N-
Ar = 2,G-di-t-Bu-C,H3 Huang, 1.; Grisa, G.; I\lolan. S.P. Org. Zn.tt., I Y Y Y , 1, 1307.
Section 100
p%n
A~ninesfrom IIalides
d3 n
IIN
6 %J
293
-
, NaOt-Bu, 105°C
\ /
, 2% €'d(dha)2
p p$Q PBr '
P(C-C6H11)2 Bei, X.; Gurmn. A S . ; Turner, H.W.; Weinherg, W.H. Tctruhtvlmn Iktt., 19YY, 40, 1237.
NII,
.Br
, toluene, XO"C, 30 I n i l l
Pd(OAc)2,
92%
PPh2
PPllz
Guari, Y.; van Es, D.S.; Keek, J N . N . ; Kamer, P.C.J.;yjul Leeuven. P.W.N.M. letruhedr-on Lm., I99Y, 40, 3789.
jf.l
P ( ~ - T O I,)2eq ~ NaOt-Bu 2% P d ( d t ~ ) dioxane ~, 3
c9
n
IIN
Br
0
6 2) 76%
(10 : Beletskava. I.P.; Bessmertnykh, A.G.; Guilard. R . Tetruhedr-on Lett., ZY9Y, 40, 6393.
Tripathy, S.; I,e Blanc, K.;J h r s t . T . Or-g. Ixtt., 1999, I, 1973.
294
Compendium of Organic Synthetic Methods, Vol 11
PhNHMe , f-BuONa , rt
-
1% Pd(OAc),, toluene, 19 h G 4% t-B~zP(2-Pb-C6€14)
N
Section 101
W
e
P 98%
Wolfe, J.P.; Quchwald. S .L. Angew. Cheni. lnt. Ed., 1999, 38, 2413.
SECTION 101: AMINES FROM HYDRIDES
0
HCHO ,BtOZCCII~NHz*llCl 10% Y (OTf), , aq TI-IF
*
N
I
30"C, 4 h
& N H C H ~ ~ ~ E ~ N
I
81%
COzEt COzEt Zhang, C.; Dong, .I.; Cheng, T.; LLB,Tetruherlrnn Lett., 200Z, 42, 461. NHPh PhNH, ,'Il3AF*3 H20 KMnO, , DMF rt,Ih
I
75%'
NO2 I Tetruhedron L d t . , 200Z, 42, 3439.
mo"
Huertas, I.; Gallardo, I.;
PhCHO , piperidine ,5 tnin
/
/
inicmwaves
70% Sharifi, A.; Miizaei, M.;
Mnnut. Chenr., 2001, 132, 875. NIIZOII , KOI-I, EtOII ZIlClZ
BaMte, J.M.; Svensen, H.; Trevisan, R. J. Chcwi. Snc., Per-kin Truns. I, 200Z, 376.
Section 102
Amines from Ketones
TBAF.3
NO2
1120,
295
PhNlI2
NIIPh
hv , DMF, rt , 3 h
NO2
Juertas, I.; Galludo, I.; w e t . J. Tttruhedron Lett., 2000, 41, 279.
54%
1% BINAP, 12 h 90%
Hicks, F.A.;
Ph
L
Org. Lett., 2000, 2, 219.
ph
y
MtONIiz, MLOII,NaOMe 4h
Ph%ph
0
0
Seko. S.; Miyake, K. Synth. Coriznim., ZYYY, 29, 2487
83%
-2: dPh
SECTION 102: AMINES FROM KETONES
1 . t-BuSONH2, Ti(OEt), 2. MeMgBr
3. IICl/MeOII
N
N Shaw. A.W.; de Solms, S.J.Tetruuliedron Lctr., 20lll, 42, 7173.
quant (60:40 -:+)
1 . Ph2NNH2, PhH , MS 4 , 4 , 6 h 2. TFAA , 0°C , 3 h
3. heat, 3 h Miyata, 0.;Kimura, Y.; &to.
'I'L Synthesis, 2001, 1635.
1
Ph
81%
296
Section 102
Compendium of Organic Synthetic Methods, Vol 11
0
1 , Me2N O
N
% >
DMSO , KF/AI2O3 2. Me1 Moskalev, N.;
-
/
'Me0
MeZN
-
60%
Chenr. Coninrun., 2001, 1248.
PhNI-12 , Montmoiillonite KSF
I
10 h
Ph
0
Samajdar, S.; Becker, F.F.;
Heterocycles,2001, 55, 1019.
96%
Kotsuki. H.; Mehta, B.K.; Yanigisawa, K. Synlott, 2001, 1323.
N I IT01
Tol-NII2, BloHl, , MeOII, 1 h
*
\I\
97%
Bae, J.W.; Ixe, S.11.; Cho. Y.J.; Yoon. C.M. J. Cltctn. Soc., Perkin Truns. I, 2000, 145. BnNII, , microwaves 30 sec
,
0
.
Tetruhedron L.ztt.. 1999, 40, 3957.
90%
l.O.l%Pd(OAc)Z,1.4 NaOt-Bu
"11, PhA
I
Bn
0.1%)Xantphos , toluene , XOC
h
2. cyclohexanone , EtOII TsOII*OM, , ieflux
N
H
Wagaw, S.; Yang, B.H.; Buchwald. S.1,. J. Am. Cfiern.Soc., 1999, 121, 10251.
92%
Section 103
Amines from Nitriles
297
1. N€IdCl, Ti(0i-Pr), , EtOII , NEt3 83% It, 10 h Ph 2 . NaBH, ,rt , 7 h .,., . BhdttdLhdTVVd.; Neidigh, K.A.;Avery, M A . ; Williamson, J.S. Synleit, ZYYY, 1781.
Ph
CI0,Et N€I2NHMe*I-ICl, EtOII 0
4
0 CCll E
n:fl ux
t
+
+
E t o 2 C c N
I
N’
I
Me
Me
1) 70%
(3
Martins. M A P . ; Freitag, K.A.; da Rosa, A.;Flores, A.F.C.;Zanatta, N.; Benacorse, H.G. J. Heterocylic Clwii., 1Y9Y. 36, 217. Related Methods: Section 94 (&nines from Aldehydes)
SECTION 103: AMINES FROM NITRILES
I’hCN
IdiBHj-NMeZ, THF , 6 Y C
*
PhCHZNI12
75 %
12 h Thomas, S . ; Collins, C.J.;Chzens, J.K.; Spiciarich, D.; Goralski, C.T.; J. Org. Client., 2001, 66, 1999. S% Ni/S02 , 10 attn H,
2M NI-I,McOH, 120°C 6h Takamizawa, S.; Wakasa, N.; PhCN Tcith, M.;
M
Synlett, 2001, 1623.
Ni(R) , NaII2IO2 , TsNI-INH,
5
A m r , € 1 ~P 0 Y , ,r t Tciralwtiron Ixtt.. 2001, 42, 2723.
e
O
\ /
PhCf I- NNIITs
e
7
96%
sponge Ni , € I 2 ,28% aq NH3 EtOII ,it, S h
a ,. Cl landkd.;Nagasawa, M.; Kasuga, Y.; Sakamura, 11.; Takuiia, Y.; Iwatani, K. ,
,
l’eiruhcrlron La., I Y Y Y , 40,5885.
86%
r
Section 105
Compendiuin of Organic Synthetic Methods, Vol 11
298
1 . EtMgBr ,Ti(Oi-Pr)4, ether
phd 70% ~
2. BF3eOEt2
Ph-CN
Bertus, P.; Szvmoniak. J. CI~eitt.Continun., 2001, 1792.
SECTION 104: AMINES FROM ALKENES
A
/(>
n
ph
NH2
cat
,CO/H2
+
€INx>
[Rh+(cod)(q6-PhBPh3)7
78%
Ph
- d-
Tetruhedron Lett.. 2001, 42, 2423.
Lin, Y.-S.; El Ali, B.;
22% Ph
cat dipho.~hiiio-~yclobutene Pd complex
Ph\ -
92%
toluene, PhNH2,S h
Ph ; Yoshifuji, M.
Minami, T.; Okainoto, H.; Ikeda, S.; Tandca, R.; Angew. Clieiti. Int. Ed., 2001, 40, 4501.
v
Ph
piperidine ,cat BuLi ,TIE
-78°C
6
It
* I
Tetrulzedron, 2000, 35,5157.
IIartung, C.G.; Breindl, C.; 'I'illack, A.;
moEt
Et2NI1, CO/H2 [Rh(cod)C1]2
Rische, T.; Bsrfacker, L.;
SECTION 105: Ph,P=O
*
91%
-Et Et2NO 75%
Eiir. J. Org. Cheni., I Y Y Y , 653.
AMINES FROM MISCELLANEOUS COMPOUNDS 1. MLOTf, DME, r t , 2 h
Ph,P 2. I.iAlI14, 0°C , 3 h h u n p t o . T.; Kikuchi, S.4.; Miura, T.; Wada, Y. Org. Lett., 2001, 3 , 87.
97%
Section 105
Ainiiies from Misc.
HC02NH4, IO%Pd-C
299
-c
NH-HCI MeOH,rt, 14h Zacharie. B.; Moreau, N.; Dockendorff, C. J. Orb. Chenz., 2001, 66, 5264.
NHz
95%
1. acetophenone, PhN 2. Bu3SnH, AIBN , PhH , 80°C
*
A
86%
Ph
Jdm&dJL; Plotkin, M.A.; Viswanathan, R.; Prahhakaran, E.N. Orb. Lett., 2001, 3, 1009.
.
95% 1101.
Hsiao.;Rivera, R.; Yasudn, N.; Hughes, D.L.; Reider, P.J. Orb. Left., 2001, 3,
Ph3SnH, AIBN, FhH
*
Crich. D.; Ranganathan, K.; Huang, X. Org. Lett., 2001, 3, 1917 /ph
Ph€IC=N
+
/0 -
Boruah, M.;
1. AlCh.6 HzO , I([,
MCN
*
2. NazS203, H 2 0 , I t
PhHC=N /ph
Synlett, 2001, 795.
UN3
2 eq PMe, , toluene, 10 eq Me1 CHZClz, 25°C , 1.5 h
Kato, H.; Ohmori, K.;
’
85%
Synlett, 2001, 1007.
90%
Section 105
Coinpendiuin of Organic Synthetic Methods, Vol 11
300
1. Meo-%
0 ~
2. NaOH , HzO2 Ph& 3. MeLi 4. NHzOSO3H Hoffmann.;Hiilzer, B.; Knopff, 0. #rg. Lc.tf., 2001, 3, 1945.
(t-BuO),C=O , 10%Pd-C , 3 h
PhNHNHZ
Z-
EtOH , 3 PHMS Chandrasekhar. S,; Reddy, Ch.R.; Rao, R.J. Synlert, 2001, lS61.
st a u 3 PI1
&
N
~
BuLi , THF, -78°C
high % ee
85%
PhNHBoc
-AI1111111111
46% (9870 ee) + 13% of 2 other isomers Pearson. W.H.; Stevens, E.P.; Aponick, A. Tetrulzcdron Latt., 2001, 42, 7361.
N -OH PhzSiH2, 1% RuC12(PPh3)
-- HZ
AgOTf, DME , rt , 2 S h 62% (83% ee)
Takei, I.; Nishihayashi, Y.; Ishii, Y.; Mizobe, Y.; Chent. Conitiiun., 2001, 2360.
2.5 BF,.OEtz , 0, MS 4 A ,CD,CN, 1 h
OH . . a m i z u . M.; Makino, H. Tctruhedron k t t . , 2001, 42, 8865.
Section 105
Fh\L-~
301
Amines from Misc.
~ , S i n , 1%r
e
A
Ph,
,OH
+
85%
DMF,H,O,lSh
Ph I1 Laskw, D.D.;
Ph Sandhu, J.S. Tetruheclron Lett., 2001, 42, 7883.
m > e Melo. T.M.V.S I q e s , C.S.J.; Cardoso, A.L.; Gonsalves, A.M.d’A.R. Tetruheclron. 2001, 57, 6203. *s;
4 eq In, IICl , aq THF ,30rnin -- PhNH2 84% I’ hNO, Lee, J.G.; Choi, K.I.; Koh, 1I.Y.; Kim, Y.; King, Y.; Cho. Y.S. Synthesis, 2001, 81.
c +
N-0
-
CN
LiCl , NaBII, , TIII:, 0°C It
*
Ram, S.R.; Chary, K.P.; k r a r . D.5 Synth. Cottinrim., 2000, 30,351 1. *&
-
98%
ZiCl, , NaBII, , ‘I’HF P hCI-I, N, PhCH,NI-I, 95% Chary, K.P.; Rain. S.R.; Salhuddin, S . ; m r . D.S, Syrith. Com/nun., 2000, 30, 3559. NaBH,. LiCl ,TIIF
P hCI I, N, Ram, S.R.; Chary, K.P.; .-
C
l
\ U/N
* PhCH,NII, 0 ° C . rt D.S. Synth. Conrrriun., 2000, 30, 4495.
FeSO4.7 HZO, NH, , rt
,
MeOH, 2.5 h
KJmdl.; , , Laxman, E.; hriludtlin, M. Totruhedron k t t . , 2000,41, 7743. Ph,+
O, N
II
;-
95%
- r I n B r
Ph,
I
N
98%
,ON
* 90% DMF,IIZO rt,3 h Anjaneyulu, S.; Reddy, E.J.; Yadav, J.S. Tetruliedi-on Lttt., 2000, 41, 9311.
A. II Ph
302
Compendium of Organic Synthetic Methods, Vol 11
N-OII
NH2 OH
NH2
of:
I-I2
cat 48%
/
Section 105
HBr
/
/
(23 1) 94% I.W*; Taylor, M.; Marcoux, J.-F.; Matty, L.; Wu, .I.; Hughes, D.; Reider, P.J. Tetruhedron Ixtt., 2000, 41, 8021.
PhCX2N3
aPhCHzNH2 NrrBI14, aq T H F , I S T , 30 min Bosch, 1.; Costa, A.M.; Martin, M.; F.: V 1 Org. Lett., 20110, 2, 397.
In, 4 NHdCI, MeOH
CN GN -
heat,4h Yadav. J.S.; Reddy, B.V.S.; Reddy, M.M. Tetruh~clronk t t . , 21100, 41, 2663. cat
a
,s.
0
NMRq Me e
i
PPh,, H2O/PhMf 5% TBN3 Wang, Y.; Espenson, J.H. Org. L.ett., 2000, 2, 3525.
p
NaBH4, C ~ C 1 2 4H
2 0
y
2
97%
Ph 1120, 10inin Ph Ringuelli, F.; Plzzo.; Vaccaro, L. Synthesis, 2000, 646. FtCl3-Zn , EtOH ,rt , 4 h
Pathak, D.; Laskar, D.D.; Prajapati, D.; NH2NMe2, FtCl,*6 H20
I
.-
PhNH,
98% Cknr. Lett., 21100, 816.
-
PhCH=N-NMez MeCN , reflux, 8 h Barrett, I.C.; Langille, J.D.; Ken, M A . J. Org. Chern., 2000, 65, 6268.
PhCH2N3
93%
quant
t
PhN,
97%
quant
Section 105
Amines from Misc.
303
+a $
1. 2 q €Ig(ClO,h*3 € 1 2 0 ,TIIF 2. NaBII4, NaOH ,M a 1 1
31%
Pearson. W [I.; Ilutta, D.A.; Fang, W.-K. J. Org. Chem., 2UUU, 65, 8326.
-
SnCl4, CHzClz Et,Si€I , 5.3 ,h0°C
Nl
B
G
N
H
M
e
91%
Lopez. F.J.; Nitzan, D. Tetruherlron Lett., ZY99, 40,2071.
-
drn dTY::;
In , NH4Cl, EtOII ,wflux, 1 h PhCHlNII, PhCH2Ny Reddv. G.V.; Rao, G.V.; Iyencar, D.S. Tetruherlron Ixtt., 1999, 40,3937.
Bu3S1iH,mm
-
I1
98%
82%
NIC:
RdlnLr.;Kennedy, .
1
I’hN3
A.R.; Chase, E. letruliedron Lxtt., ZYYY, 40,6 3 2 5 .
EtMgBr ,ether, 30min
*
PhNIlEt 90% &mar. H M .S.; Reddy, B.V.S.; Anjaneyulu. S.; Yadav, J.S. Tetruhedron Lxtt., 1999, 40, 8305.
mBr , DMF ,211
PhN,
>
82%
it , 40inin Kumar. I I .M.S.; Anjaneyulu, S.;Reddy, B.V.S.; Yadav, J.S. Syrrlett, 1999, 551.
Ph (P PD )I IN 1 . B uLi , TIIF , - 7 8 T
CN DPP
Ar
= 4-MeO-CGJI4
Ar
Ar
(60
40) 81%
KdlSLT.; . Balhi, M . Z’e~ruherlrnnAsynini., ZYYY, 10, 1001. I .
304
Section 105
Coiiipendiuin of Organic Synthetic Methods, Vol 11
MCM--silylamine-Pd(I1) complex
N 1.1,
MeOH, rt
92%
Kdntdm.; . . Chowdari, N.S.;Rahinan, S.; Choudary, B.M. Synlett, 1999,1413.
AMINES FROM NITRO COMPOUNDS FhNOz
porphyiinato-ion / NaBH4
*
PhNHz
HOCI.I,CI12Br, it Wilkinson, 11,s.; Taiioury. G.J.; Wald, S.A.; Senanavake, (7.11. Tefruhedron L.ett., 20f11, 42, 167.
95 %
M~N-BII~ pd(orr)2/c ,
* PhNHz 90% MeON, r t , 6 h Couturier.; Tucker, 1.L;Andresen, B.M.; Dub&, P.; Brenek, S.J.;Negri, J.T. Tetruhedrcin L.ett., 2001, 42, 2285. PhNOz
N,tI,*M2*H20 , A 1 2 0 3 , FtCh.6 €120
c PhNH2 inicmwaves, 5+2 inin , 108°C Vass, A.; Dudbs, J.; ’I’Gth, J.; Vnnnn. R.S.Tetruherllnn Lett., 2001, 42, 5347.
PhNOz
57% In, 9 0 , c , 4 h
KumAr, 1.S.D.;Ho, M.M.;
‘
89%
* =+-N z(I-r 85%
Tc~tr-uherlronLett., 2001, 42, 5601.
FeS-NH4C’I , aq MeOII
* PhNHz reflux, 4 h 81% Desai, D.G.; Swami, S.S.; Dabhiide, S.K.; Ghagnre, M.G. Synth. Cninrnun., 2001, 31, 1249. PhNO2
(16 Kang, K.H.; Choi, K.I.; Koh, H.Y.; Kim, Y.; Chung, B.Y.; Choi. Y.S. Synth. Continun., 2001, 31, 2277.
1) 51%
Section 105
PhNO, Yu, C.; Liu, B.;
305
Amines from M i x .
2 txj Sni , 5 % 1,511ioctyl-4,4'hipyridinium dihromide I
83%
PhNH,
M&H, rt , 3 h J . Org. Cheni.,2001, 66, 919. B,,H14 , Pd-C , a t AcOH
0 2 N - o -
C0,I I
I 1 2 N e c o , H
\ /
+
MLOI-I,reflux , 0 0 inin
97%
Bae, J.W.; Cho, Y.J.; Lee, S.11.; Yoon. C.M. Tctruh<,rlronIxtt., 2000, 41, 175.
Ph-NO,
mBr ,4eqSn
-
Ph-mn, McOH, 20 h Bieher. L.W.; da Costa, R.C.; da Silva, M.F. Tetrulirclrnn Lett.. 2000, 41, 4827. ZiC14 , NaBI-i4, THF , 6 h PhNO, Chary, K.P.; Ram, S.R.; Jvenvur. D.S. Synlett, 2000, 683.
PhNOz
Ni1112IV2/FeSO4*7 H I O , 50 sw
92%
PhNII,
L
72%
78%
P11Nr12
miLi-ow aves J'vleshram. 1I.M.; Ganesh, Y . S . S . ; Sekhar, K.C.; Yadav, J.S. Synletr, 2000, 993.
4 rq S i n , 20 eq NHdCl
h 4 ~ 0 1 1 ultrasound, , 10 min Basil, M.K.; Becker, F.F.; Dwiik.
P hNO,
B.K. T~~trulic~rlrort Lett., 2000, 41, 5603.
Cu(BI12S3)2,THF ,reflux t
PhNH,
90%
2.5 h
also fiwn ArN3 F;irouzabadi. 11.; Tamiiini, B.; Kiasat, A.R. Synrh. Conirnun., 2000, 30, 587.
PhN02
Ni(N07)6 €I,O , AI(NO3)s) IIzO t
NaOII , Na,C03,313"K, 13 h
PhNz
Juuthl.;Raja, T.; Talawar, M.B.; Sreekumar, K.; Sugunan, S . ; Rao, B.S.
95%
Synth. Coniniim., 2000, 30, 1573.
IICOOII , Ni(R), Me011
EtNH, * 50% 10 inin G;owda. D.C.; Gowtla, A.S.P.; Baha, A.R.; Gowda, S . Synth. Conmun., 2000, 30, 2889. EtN02
306
Compendium of Organic Synthetic Methods, Vol 11
Section 105
HCOzNHd, &OH, It, 1 h Gpwda.
PhNO,
E; Mahesh, B. Synth.
PhNIIz
_.
Coniniun.,2000, 30, 3639.
90%
In ,NH4C1, XI EtOH
t PhNH2 90% 5h Banik.; Suhendra, M.;Banik, I.; Becker, F.F. Synrli. Conitnun., 2000, 30, 3145.
PhNO,
aNH /
-
65%
. .
Ishivaina. Y.; Maema, R.; Ohno, K.; Hirose, M.; Sonoda. N. Tetruhedron L.ett., 1999, 40, 5711.
Sm , trace 1, , ay THF-NH,CI
PhNOz
*
+
PhNH,
4h
PhNHNHPh
5 6%
20%
Wang, L.; Zhou, L.; Zhang. Y. Synlett, 1999, 1065. 0.2 ClCl, , 16 eq Mn powder
TIIF, 8 eq TMSCl 83%
Hari, A.; Miller. B.L. Angew. C h m . Int. Ed., 1999, 38, 2777. PhNO,
FtC 1, -Zn-DM F--I I 2O
*
PhNII,
100°C , 3 0 min
D.G.; Swami, S . S . ; Hapase, S.B. Syntli. Coniniun., 1999, ZY, 1033.
92%
R EV IE WS : " [ 3 + 2 ]Synthesis of Pyirolizidine and Indolizidine Alkaloids," Broggini, G.; Zecchi. G, Synthesis, 1999, 905. "Synthesis of Secondary &nines," Salvatore, R.N.; Yoon, C.H.; Tetruherlmn, 2001, 57, 7785.
m.K.W,
Section 10%
307
Protection of Amines
"A Coinparison of Imine-Foiining Methodologies," Love. B.E.; Boston, T.S.; Nguyen, B.T.; Rorer, J.R. Org. P w p . Proceed. Int., 1999, 31, 399.
SECTION 105A: PROTECTION OF AMINES
P
Gruhhs' catalyst toluene . reflux
1 .
I
II
Alcaide. B.; Almendros, P.; Alonso, J.M.; Aly, M.F. Org. Lett., 2001, 3 , 3781.
.+ dn
1. BnOH , DCC , DMAP , M K N 2. NaBH4, EtOH
NHCOCF3
Barker, D.;
85%
; Brunhle, MA.; Savage, G.P. Tetruldron Lrtt., 2001, 42, 1785.
i-PiOH , 4 eq HC02NI14 10% PdIC miciuwaves (1 inin x 3 cycles)
95% Daga, M.C.; Tacklei. M.; Varchi, G. Tetruhedron Zxtt., 200Z, 42, 5191.
lO%[Ni(hipyh](BF& e- , Zn anode, DMF
PhN€IZ
/
PhHN Franco, D.;
m\
78%
Tctruiiedron Lett., 20011, 41, 7333.
07
e' , DMI:
/
N
76%
I H S02NMe2 Largeron, M.; Fxrell, B.; Rousseau, J.-F.; Fleury, M.-B.; Potier, P.; Tetruhcrlron L z t t . , 2000, 41, 9403.
+
HSO,NMe,
Section 105
Compendiurn of Organic Synthctic Methods, Vol 11
308
CF3COzEt 0.1 DMAP 20 h , 8 5 " C , TIIF
Prashad.;IIu, B.; Har, D.; RepiE, 0.;Blacklock, T.J. Trtruhedron Len., 2000, 41, 9957.
Sassy. J,; Rakotonrisoa. 11. Tctrulic~dronloft.,2 0 M ,41, 2007.
, 10% PdJC
B
n
CN-B
O
11
EtOH , 22°C
-
BnO
72% Slade, J.; RepiE, 0.;Blacklock, T. Tetrahedron k , f t . , 2000, 41, 6021.
;-
PhzN\
=
Rele, S.; Talukdar, S.;
TiCI,*Li-TIIF, THF , 2 Y C
Ph,NH
t
75%
Tt,truhi,rlronLrft., 1999, 40, 767. PhzS NEt, i(C,HZffIzOTs), DMF t
A
( - t . V S P h z
L I'BN:, THF
90%
aB.M.; Cho, J.H. Ti,truhi,rlron L&t., 1999, 40, 5333. AlCI:, ,CHzCIz, 2 h Ph-NHBoC Bose. Q&; Lakshminarayana, V. Syntliesis, 1999, 6G.
* Ph-NHz
B n 0 2 C N (SOFF3)(4-CF3-GH4) TIIF, r t , 0.1 h
Ph-
88%
NI IChz
95% Y.; Toinioka. K. J. Cltcin. Soc., Perkin Truns. 1,1999, 2233.
Section 105A
Protection of Amines
309
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 8
PREPARATION OF ESTERS
SECTION 106: ESTERS FROM ALKYNES
=
F'h
Ts0I-I , silica , DCM
SMe
40"C,2h
*
PhJ
a0 86%
SMc
BrJra.;Martins, T.L.C.; Silveira, C.C.; Rodiigues, O.E.D. Tetrahedron, 2001, 57, 3297. '
1
CO , I I 2 0 , PdI2/KI , 80°C
3
-B
dioxruie , 15 h
*
65%
0 Gahriele, B.; Salcrno, G.; Costa, M.; Chiusoli, G.P. Tetrulwdron Lett., 1999, 40, 989. 10
Bu-
c o , co, , 200 eq Irzo
PdI, , 1 0 a 1 KI , dioxaie , 15 h
Gahriele. B.: Salerno. G.;Costa,
*
77%
M.;Chiusoli, G.P. Chem. Cnmniun., 1999,
1381.
SECTION 107: ESTERS FROM ACID DERIVATIVES The following types of reactions are found in this section: 1.
2. 3.
Esters from the reaction of alcohols with carboxylic acids, acid halides and anhydrides. Lactones from hydroxy acids Esteis from carlloxylic acids and halides, sulfoxides and miscellaneous compounds
.- PhCI-I,C02Me 2. MLOII T . h Tctrnlierlr.rmL d . , 2001, 42, 3959.
PhCI 12c:0211 Dyke, C.A.;
m.
94%
Section 107
Esters finin Acids
311
CBr, , MLOII, hv , it , 1 d
BrqCIl2)>
C021I
* BrqCH2)>
selective for non-conjugated ackls Lgg, AS.-Y,; Yang, H.-C.; Su,
C0,II
mo
I:.-Y. Tetrulzerlron Lett., 2001, 42, 301.
3 eq
.MKN 4
CIIO
~XJ NEt,
L
c02Me 98%
55%
, 25°C
Coretz, G . S . ; Tennyson, R.L.; Ronio. D, J . Ant. C17ern. Soc., 2001, 123, 7945.
Vignola, N.;Dahmen, S . ; Eiders, I).; Brilse.Tetruher/r-on Lett., 2001, 42, 7833. BnBr , 5 txj K P 2 1 1 9 , 3 h
*
Ph-C02H
Ooi, T.; Sugimoto, €I.; Doda, K.;
P hCY),I I
5% BuJ'tIISO, , THF, rt . Tetmlierlrnn Lett., 2001, 42, 9245.
t-BuOH , N 2 0 3 Zn , dust, DCM
sulfur suhlinate , rt KdTmrlkrlT.; . . . Das, P.J. Synfh. Contriinrr., 2001, 31, 535.
P hCD2 N
-CO,Bn Ph
Ph02t-Bu
99%
90%
EtOI-I ,276 Fe(SO4h.x H20
> I'hCO2Et 97% GI~II~SO, Xu, Q.-h.; Liu, W.-y.; Chen, B.-h.; Ma. Y.-x. Syntlz. Cornriiun., 2001, 31, 2113.
1. MeOII, 6S"C, H 2 0 , 1 h
P hCW2I-I
microwaves
+ PhCO2Me 84% 2. I-12S04 Zhane. z; Zhou, L.; Zhang, M.; Wu, II.; Chen, 2. Syntli. Coninittn., 2001, 31, 2435.
Q-c'." ;-
. . .
MsCl , Py , O T , 40min
>Q
Begum, F.; Begum, S . Tc,truhcdron Lett., 2001, 42, 9059.
C02Me
71%
312
Coinpendiuin of Organic Synthetic Methods, Vol 11
: -
toluene, 100°C
-
Section 107
3
97%
cat [Ru[ PhCII=C(Ph)CnCPh)(PMei-Pr2 }]
JimCnez-Tenorio, M.; Puerta, M.C.; Valerea. P,; Moreno-Dorado, F.J.; Guerra, F.M.; Massanet, G.M. Chern. Corninun., 2001, 2324.
coZH
@
COzMe
KOI:i:Y:O.MeI
Br Br ,4vila-Zirraea. J.G.; Mariinez, K.Synfh. Coniinun., 2001, 31, 2177.
-
BuOH , NdlSOd*IIlO
BtCO,€I
94%
EtC02Bu
&
96%
x f l u x , 3 0 inin Li. Y.-0. Synrlr. Cor~iiiiun.,I Y Y Y , 2Y, 3901. Ac20 , Zn/AlC13 , DMF
PhSSPh
; -
... ,
.
PhSAc 65°C. 4 h Fadaei, Z. J. C h m . Res. (S), 2001, 22. I
.
80%
COT1I
CXHI7OH -coZcSH M%N*HCI ,NEt, ,0°C * Ph MLCN, 3 h Wakasugi, K.; Nakamura, A,; w w .Y, Te.trulie(IronLL'tt., 2001, 42, 7421. Ph
w Ph
C
0
2
H
CXH ,,OH , toluene , 80°C , 4 h diphenyllrinmonium tiifh te
*
Ph-
17
93%
c02c&17
93% Wakasugi, K.; Misaki, T.; Yainada, K.; Tanahe. Y. Tetrulledron Lett. 2000, 41, 5249. MeC02II
BnOH , act. C , miLrowaves
L, MtC0,Bn 12 sec Sapar..;Shinde, N.A.; Bandgar, B.P. Org. Prep. Procc~cd.Irit., 2000, 32, 287.
ji,,,
Ph
83%
BnSII , 4 eqP41II0,toluene llO"C, 4 h
PhSBn'
Sudalai, A.; Knnagasahapathy, S.; penicewicz. B.C. Org. k i t . 2000, 2, 3213.
96%
Section 107
Esters from Acids
9.."
313
MeOH, NaHS0,-SiO, 45 h q
96%
H
C0,II
C0,Me
cr cmzH
Das.;Venkataiah, B.; Madhusudhan, P. Synlett, 2000, 50. 1. SOCl, , Arnherlyst A21
DCM
2. MLOH
Ir
Girard. C.; Tranchant, I.; NiorE, P.-A.; Ilerscovici, J. Syrrlett, 2000, 1577. PhCH,CO,I-I
NaI-IC04-Si02, EtOAc
+
Phff-I,CO,Et
rt,6h Das.;Venkataiah, B. Syntliesis. 2000, 1671.
* Bu
Br'(collhPF6, CHzCb
95%
,yflr
60%
Bu
Homsi, F.; pousseau. G . J. Org. Chetn., 1999, 64,81. P hC0,I-I
89%
EtOH , 2 eq Py , DCM ,rt
*
95%
Pha,Et
Isohe, T.; Ishikawa, T J . Org.Chon., 1999,64,6984.
-ti.
1. LiOII , IIzO
-
I' hC0,Me 2. MqSOd A K .; Basak, A.; Grover, V. J. Org. Chent., 1999,64,8014.
PhCY),II
1
Ph
CO,II
MtOH, F~(SO,h-xH,O itflux, 3.5 h
9G%
-1
G.-S.; Gong, 11. Synth. Conirnctn., 1999, 29, 1547.
I'h
COZMe
83%
Compendium of Organic Synthetic Methods, Vol 11
314
20%F%( SO4h.x HZO ,M&II
PhCOzH
4h Synth. Conintun., 1999, 29, 607.
L.
Section 108
PhCOZMe
82%
Further examples of the reaction RC@H + R'OH --P RC02R are included in Section 108 (Esters from Alcohols and Phenols) and in Section 30A (Protection of Carhoxylic Acids).
SECTION 108: ESTERS FROM ALCOHOLS AND THIOLS
C6H13
;-
1
DEAD, PhMe ,PhCOOH polymer-hound phosphine
QBz
*
--
rt,lh c61113 Janes, M.K.; Boezio, A.A. J. Org. Chenz., 2001, 66, 2178.
83%
\ , A T&phlo Ph
Ac@ , DCM + 99% 1 % V(O)(OTf), ~ e n . C 30 min .- ; Kuo, J.-H.; Li, C.-H.; Barhate, N.B.;Hon, S.-W.; Li, T.-W.; Chao, S.-D.; Liu, C.C.; Li, Y.-C.; Chang, I.-H.; Lin. J.-S.; Liu, C.-J.; Chou, Y.-C. Org. Lett., 2001, 3, 3729. AczO, YEr based catalyst 0
-
O
4h
.
2
Kurnar.; Pandey, R.K.;
99% (also with amines) Bodas, M.S.; Dongare, M.K. Synlett, 2001, 206.
2 eq A ~ ,O cat L~QO,
25°C Ph Nakae, Y.; Kusaki, I.; Sato. T, Synlett, 2001, 1584.
IIzN
011
graphik/montmonlloriite K10 mimowaves, 8 m i n , 130°C
-
HZN Frkre, S.; ThiCry, V.; w o n . T, Tetruhedron Lett., 2001, 42, 2791.
61% 0
Esters from Alcohols
Section 108
315
AczO ,cat NBS ,C€12CI,
PhCHzOH
>
rt,4h . . Kanml.; Seradj, H. Synlett, 200Z, 519.
PhCHzOAc
94%
AgzO, TsCl , KI , 2 0 T
won
M t a-ors
*
MeO
60%
UA.;Le Berre, N.;Sauv6, G . Terruhedron Lett., 2001, 42, 8781.
[hmim]C1*2 AICI, ,3O"C
Iro
OM
EtOAc , 10 min HO ~~
Potdar, M.K.; Mohile, S.S.; Salunkhe. M.M. Tetmhedron Lett., 2001, 42, 9285.
95%
DCC , DMAP , DCM lSCPa,rt, 1 d 92%
Shlmlzu.;Hiramoto, K.; 1
.
.
Synthesis, 2001, 1027. Ti04/S04-2, MeOH
96% Ph COzH reflux, 2 h Ph &n. T.-S.; Ma, Y.-R.; Li, Y.; Sun, X . ; Li, T.-S. Synth. Conintun., 2001, 31, 2051. Pd(II)-hydrotalcite, F'y ,Oz OH
*
56%
toluene, 8O"C, 28 h
0 Kakiuchi, N.; Nishiinurn, T.; Inoue, M.; Uemura. S . Bull. Chent. Soc. Jpn., 2001, 74, 165.
PhCH,OI 1
AcOII ,BiCl, , 1 h
z
PhCI-120Ac
95%
v; Khosrupour, A.R.; Aliyan, 11. J. Chent. RES.(S), 2001, 280.
Compendium of Organic Synthetic Methods, Vol 11
316
f
i
s
2. 1 .P T BAAPFii NMO THF
Section 108
dT:
c 3H 7
(45% ee)
GH7 Leroy, B.; Dumeunier, R.; M i u k L E Tetruhedron Lett., 2000, 41,10215.
Okada.;Iwashita, S.; Koizumi, N. Tetruhedron Lett., 2000, 41,7047. 1. CCHzCN , AcOII
Et,C-OH ;-
1
.,
*
HZSO.4 + Et 3 C-N H3C I 2. thiourea, AcOIIlEtOH Kauss, V.; Kalvinsh, I.; Gold, M.R. Syntlzcsis, 2000, 1709.
Ph
pL
%;.
BuBr ,C s 2 c 0 3
OH
Chu, F.; Dueno, E.E.;
a
L
o
Tetruhedron Lctr., ZYYY, 40,1847.
2
;co)3c% M a
TBN , DMF, 93”C, 1 d
,PhH, 3 NEt3
ultiasound , 3 h
89%
/
y Bu
91%
M a
0
/ \ -
Caldwell, J.J.; IIamity, J.P.A.; Heron, N.M.; Ken-. W.J.; McKendiy, S.; Middlemiss, D. Tetruhadrnn Lttt., 1999, 40,3481.
pL OH
BnC1, Cs2C03 CO, , DMF ,TBAI ,23”C , 4h
Ph L
y
o
B
94% 0 Kim, S . 4 ; Chu, F.; Dueno, E.E.; Jung, K.W. J. Orx. Charn., ZYYY, 64,4578.
n
317
Esters from Aldehydes
Section 109
N-trifluoroacetylsucinimide
C,,I 1~,0r I
*
18 H3
7OZCcF3
95%
THF ,refhx , 5 h A .R.; Yang, B.; Qiu, G.; Zhang, Z. Synthesis, 1 Y Y 9 , 55.
-v.
1. C 0 2 , Bu3P, CyTMG , DMF
* PhCH20C02CII2Ph 2. CBr4, 2 h KddokrlWd.; . IIaliu, 11.; Fukumachi, S.; Karasu, M.; Tagaya, H.; Chiha, K. J. Chent. Soc., I'cr-kin Truns. I , I Y Y 9 , 2205. P hC3IZOI I
67%
Further examples of the reaction ROH + RCOzR' are included in Section 107 (Esters from Acid Derivatives) arid in Section 4SA (Protection of Alcohols and Phenols).
SECTION 109: ESTERS FROM ALDEHYDES
Hsu J.-L.;
m.1.-M, J. Org. Clwnl., 2001, 66, 8673.
actr0 CO$llyl
2.1.H30+ e-
*@'
Franco, D.; PuAach. E. Synlett, 2001, 806.
0
OAl(Oi-Pr)z
m
CIIO
1%
oAl(oi-pr)2
DCM , r t , 2 h Simpura, I.; H e v a w Terrulidron, 2001, 57, 9867. CI10
95%
/
-
0
A4\
Oi-Pr
0
CaO , PhlhlI ,313"K. 1Smin
Seki, T.; Ilattori. €-I. Chetn. Cnrnniun. 2001, 2510.
99%
318
Compendium of Organic Synthetic Methods, Vol 11
PhCI.10 Gopinath, R.; &&&Jj&
M ~ O H ,I , 0 2 ,cat v20,
*
Section 109
PhC02Me
quant
Org. Lert., 2000, 2, 577.
w o n . S.& ; Wan, 2.;Peelen, T.J.; Spencer, K.L. Tetruhedron Lett., 1999, 40, 6535.
a hiphenylene A1 catalyst
0
Ooi, T.; Miura, T.; Takaya, K.;
*
Tetruhedron Lett.. 1999, 40, 7695.
99%
<30% (>19:1 trms:cis) 62% (>19:1 cis:frcms)
with SnCh ,-78°C Wang, Y.; Zhao, C.; Romo. D . Org. L ~ t t .Z999, , 1, 1197. cat (Sm12 + I-PrSII) *
'
r
8
8
%
Mxc3
Org. Lett., 1999, I , 1989.
C3H7C02Na, PdC12(PPh3)t ,80"C CO PhII, 18 h Cho, C.S.; Bark, D.Y.;
*
62%
/
0 J. Heterocyclic Client., 1999, 36, 289.
Section 110
PhCHO
Esters from Alkyls
3 19
1. 2% chiral hicylic amino-alcohol Et,Zn , hexluieholuene ,0°C , 3 h
-Pi1M QAc
2. A c ~ O
98% (98% ee)
Nueent. W . 4 , Cheiii. Coirzniun., 1999, 1369.
i
cHO
0
1. (pinylhB ally1 ,ether
-1OO"C, 1 h
2. p-TsOH , heat
COzMe
8 2 ~ 9 0 %(>99% ee)
Ramachandran, P.V.; Krzeminski, M.P.; Reddy, M.V.R.; Brown. 1-I.C. Tetruhedron Asyiiini., IY99, 10, 11.
1. PhCIIO
=(C02H
TI IF/H2O 2. 6M HQ
Choudhury, P.K.; f:ouhelo, F.; 1,
PhCI-I0
,In , 2 0 0 ~
p
h
v
o
t
75%
Tetruhedron, 199Y, 55, 10779. ,0.5 TaCl5, 0°C
-S /M i e3
DCM,Ih
2. A c 2 0 , r t , 12 h
70%
Ph Chandrasekhar. S.; Mohanty, P.K.; Ram, A. Syntlz. Connnttn., 1999, 2Y, 257. Related Methods: Section 117 (Esters from Ketones)
SECTION 110:
ESTERS FROM ALKYLS, METHYLENES AND ARYLS
-
No examples of the reaction R-R RC@R' or R'COzR (R,R' = allcyl, aryl, etc.) occur in the literature. For the reaction R-H + RC02R' or R'COzR, see Section 116 (Esters from Iiydrides). 1. 1 atm CO ,CBr4/2 AlBr, CHzBr2,-40°C , 2 h
2. i-I'iOH
L.; Petrovskii, P.; Vitt, S.; Orlinkov, A. Tetruhedron Lett., 2000, 41, 9903.
C02i-k 82%
Compendium of Organic Synthetic Methods, Val 11
320
Section 111
SECTION 111: ESTERS FROM AMIDES
10%MgBq ,MeOH
Ph4
lJ Jo
N
8h
Ph&OMe
Orita, A,; Nagano, Y.; Hirano, 1.;Qtera. J. Synlett, 2001, 637.
K
ph
C ~ B r ~ l L i 0 t u- B, T€IF
NI INH 2
20 min
H2N
(
H
Ot-Bu
88%
Cheni. Zxtt., 2001, 466.
OQg(CHz0H
OH C
-1 Ph
Yamapuchi. J . - i ; Aoyagi, T.; Fujikurd, R.;
/
97%
GCN N
a
*
1120 ,75"C, 16 h Yorimitsu, 11.; Wakahayashi, K.; Shinokuho, H.; Oshima. K. Bull. Chent. Sor. Jpn., 2001, 74, 1963. O -H
H20,75"C, 16 h H PL
I
HO,VN=N=CO,W
*
O
CN water soluhle radical initiator Yorimitsu, H.; Wakahayashi, K.; Shinokubo, 11.; -K.ct!-uher/ron
m
95%
O
Lett., 1999, 40, 519.
1. CAN
O
\
2
N
GNHNH2
2. MeOH, rt
Stefane, B.; KcZevar, M.; Polanc. S. Tetruhedron Lett., Z999, 40, 4429.
*
97%
Section 113
321
Esters from Esters
SECTION 112: ESTERS FROM AMINES NO ADDITIONAL EXAMPLES
SECTION 113: ESTERS FROM ESTERS Conjugate reductions and conjugate alkylations of unsaturated esters are found in Section 74 (Alkyls from Alkenes).
Evans. P A . ; Kennedy, L.J. J . Am. C h w . SOC., 2001, 123, 1234. PhBr , catPd(dba)z, rt
Or-Bu Lee, S.; Beare, N.A.;
-
PhJ
NaNTMq ,12h
Ot-Bu
J. Am. Chem. Soc., 2001, 123, 8410.
r-BuOK , ether, 0°C EtC0,Me Vasin.;Razin, V.V. Synletf, 2001, 658.
IZovle.; May, E.J. Synlert, 2001, 967.
(98 63% ee
t
EtCOzt-Bu
2)
69%
87%
71%
Compendium of Organic Synthetic Methods, Vol 11
322
Section 113
BuOH ,L a o 4
Bdndedr.; , . Sadavarte, V.S.; Uppalla, L.S. Synlett,
88%
C0,Bu
toluene, heat, 2 h
C0,Et
2001, 1338.
C,H@H, cat NBS , 100°C toluene, 3 h
C02Me
94%
m; Uppalla, L.S.; Sadavarte, V.S. Synlert, 2001, 1715. a
1
F e S 0 4 , BuOH , toluene reflux, 2 h
uOEt
also with Cu.W4 (88%) B.P.; Sadavarte, V.S.; Uppalla, L.S. Synth. Contntim., 2002, 31, 2063.
85%
C,H@H, NaBPh, , bluene
* j j C 0 2 C J I ,
reflux, 2 h
L C O z E t
90%
b d e a r . B .PG;Sadavarte, V.S.; Ilppalla, L.S. C h m . k t t . , 200Z, 894.
-
BuOH ,Zn, toluene COzBn
heat, 2 h
Bandear.;Sadavarte, V.S.;
Uppalla, L.S. J. Chenz. Res. (S), 200Z, 16.
98%
Rucatdyst , i-PIOII
'
20"C, 23 h
C0,Me Evaraere, K.; Scheffler, J.-L.; Mortreux, A.; MeMgBr ,THF , 1 h
99% (94% ee ,S ) -
0 Tetrahedron l ~ t .2001, , 42, 1899.
b P h-S02Me 77% O"C+ It Steensma.;Calahi, S.; Tagat, J.R.; McComhie, S.W. Tetrahedron Lert., 2001, 42, 2281.
PhSO2CF3
Section 113
Esters from Esters
323
cat [Ku(acen~Cl~)]~
chiral ligand , r-BuOH Z-BuOK
OBU
Or-Bu
>99% (67% ee) Everaere, K.; Mortreux, A,; Bulliard, M.; Brusse, J.; van der Gen, A.; Nowogrocki, G.; Carpentier. J.-F. Eur. J. Org. Chmt., 2001, 275.
J
Ph
TBAFO
OSiMq
€120,
BnBr
* Ph
T H F , r t , 1.5h
96%
Ooi, T.; Sugimoto, 11.; m u o k a . I(.Heterocycles, 2001, 51, 593.
. . Wl,llld . ms.;Blann, K.; IIolzupfel, C.W. Synth. Coiiiinun., 20OZ, 31, 203.
L
BuOH , Amkrlyst-15
COzMe
toluene, =flux, 2 h
*A/ COZB u
85%
Chavan.; Suhharao, Y.T.; Dantale, S.W.; Sivappa, K . Synth. Cormzun., 200Z, 31, 289.
phho
Me4Sn , 25% Pdz(d1x&, 80°C* 10% AsPh3,10% CUI , N M P , 87 h
0 possi. R.; Bellina, F.; Kaugei, E. Synlett, 2000, 1749.
oJ--)hp
58%
0
1. dilauryl peroxide , PhH , reflux 2 . 5 eq E 6 0 , N 3 , PhCl 0
Ollivier, C.; -1.
dilauryl peroxide, 100°C
P. . I . Aiii. Cheni. Soc., 2000, 122, 6496.
N3
80% (74:26 eno:endo)
Section 113
Compendium of Organic Synthetic Methods, Vol 11
324
AOTBDMS Wang, W.; Xu, M.-H.; Lei, X.-S.; Lin, G.-Q. Org. Lett., 2000, 2, 3773. 5 eq CsOAc , 0.1 DMAP
Hawryluk, N.A.; &,&r&R
HN -OH
A
c
O
m,+" Y f 85 %
t
Ns = nifrohenzenesulfonyl J. Org. Client., 2000, 65, X379.
Lipase Novozym 435 ,65"C isooctane , MS 4A
NH
I
74%
Lu, W.; sib. C.J. Tetruhedron LEtt., 1999, 40, 4965.
;.w-
Pugh, G . Tetruhedron k t t . , 1999, 40, 7595. PhC02Me
EtOH , 4 h
*
PhCO,Et 89%
Ilankumaran, P.;
e . J . G J . 01-8.Chein., 1999, 64, 3086.
Section 114
325
Esters from Ethers
Enholm.; Gallagher, M.E.; Moran, Org. I x t t . 1999, 1, 689.
K.M.; Lomhardi, J.S.; Schulte 11, J.P.
B uOH , Mo-ZiO, , toluene
* M
reflux
Reddv. B.M.; Reddy, V.R.; Manohar, B. Synth. Cornniun., 1999, 29, 1235.
O
B
98%
REVIEWS: "Stereochemistry of the Alkylntion of Idactones,"Ihrahim-Ouali, M.; Pnrrain, J.-L.; Org. P r i y . Prori~oil.Itit., 1999, 31, 467.
SECTION 114:
i i
Bu
ESTERS FROM ETHERS, EPOXIDES AND THIOETHERS Bu
2% PPNCo(CO), , 9 0 0 psi CO
*
B1~,-Of'tz,DME , 80°C, 1 d
PPN = his(tiipheny1phosphine) iminiuin Lee, J.T.; Thomas, P.J.; J . Org. Chetn., 2001, 66, 5424.
'a,
1 . M d l s , DCE , 8 O T
B uOBu
2. BzCl ,8WC Guo, Q.; Miyaji, T.; Gao, G.; IIara, R.;
t
75%
Chetn. Conirnun., 2001, 1018.
L>' u u'. l h L ; Graziano, M.L. Tetruherlron ,!,eft., 2001, 42, 93. '
PhCO,Bu
66%
u
Compendium of Organic Synthetic Methods, Vol 11
326
9
TBDMS"'"'
1. cat Pd(0Ack , cat P(OPh), TIIF
2. MeMgBr ,-78"C, 1 h
*A Me
MaZC
Section 114
g
78% (74% de)
T~DMS
Marion, F.; Le Fol, R.; Courillon, C.; Malacria. M. Synlett, 2001, 138.
BuY30H*B
Madhushaw, R.J.; Li, C.-L.; Shen, K.-H.; IIu, C.-C.; J . Am. Cheni. Soc., 2001, 123, 7427.
P b(OAc)&3(
OAc k
78%
Py , PhH, reflux
&g&,.L&;
Payen, A.; Warshakoon, N. Tetruizerlron Lett., 2001, 42, 2047. F&13-Monftnorillonite K 10
BnOBn .: Mova
* BnOAc AcZO ,70°C, 22 h Fasihi, .I. J. Chem. Soc. (S), 2001, 378.
w; .' '
7
1 . 2 eq A d l , DCM, O T , 18 h
2 . 4 NaIICD3 Tetruhedron Lett., 2000, 41, 5799.
C 0 2 ,5% NaBr ,NMP lOO"C, 30 h OZN
[ 18% with Phuxirdne]
OZN
Iwasaki, T.; Kihara, N.; h d o . T. BidZ. Clieni. Suc. Jpn., 2000, 73, 713.
94%
327
Esters from Halides
Section 115
0
NaBrC), , KI-ISO, , H 2 0 , rt
80%
0 Metsger, L.; Bittner. S. Tetruhedron, 2000, 56,1905.
-
0
M%SiONOz /C103
65%
Shahi, S.P.; Gupta, A.; Pitre, S.V.; Rcddy, M.V.K.; Kumareswaran,
J . Org. Clterii. 1999, 64,4509.
Ph
M&gnf.
Ct,BnNCl, KMnO, , DCM
OMe
reflux, 6 h
K.;Vankar. Y.
* A
J.11.; Choi, B.Y. Synth. Conmiin., 1999, 29, 2405.
Ph
OMe
85%
SECTION 115: ESTERS FROM HALIDES AND SULFONATES Br
2.3 MtC0,t-Bu 2.5 LiI-IMDS ,toluene
C02t-Bu
3% I'd(OAc)z, 1 h 6.3% bipheiiyhminophosphiiie S'.I.. .I. Ain. Cliern. Soc., 2001, 123, 7996.
0
Moradi, W.A.;
c1
/
C O , BuOII , 130"C, 15 h 0.1 PdCI,(PhCN)2, 25 h a 0.6 dppf, NEt,
*
84%
0
COZBU
95%
Beller. M.; MSgerIeiri, W.; Indolese, A.F.; Fischer, C. Synthesis, 2001, 1098.
BuWI , CO , 3 eq NaOAc , MS O.S% [PdCI,(I'hCN)7_1 , 145°C fenoce~iyldipho-Thine MPgerlein, W.; Indolese, A.F.; Deller. M.Angcw. CllelJt. Int. Ed., 2001, 40,2856. 45 atrn C 0 , A I B N hexandMeCN , 80°C
c0,IIt ~
o
l
b S nl B u 3
, 12 h
*
do
COZEt Kreimerman, S.; JXVu. I.: Minakatn, S.; Komatsu. M. Org. Lett., 2000, 2, 389.
84%
328
-
Compendium of Organic Synthetic Methods, Vol 11
* 2. H20 Sato, A,; Ito, H.; Yamaguchi, Y.;
Section 116
CO2Et
aTetruhedron Lett., 2000, 41, 10239. '
72%
Zheng, T.-C.; Burkart, M.;Pichardson. D.E. Tetruherfr-onLetr., 1999, 40, 603.
C O , PdClz[P(OEt)& OH
2.2NEt3, 130°C , 18 h 200 a t m C 0 2 (supemitical)
ncl
Kayaki, Y.; Noguchi, Y.; Iwasa, S.;
C O , EtOII , NaOAc , 135°C Pd(0Ac)z ,dppf , 1 h
Et02C
c1
Bes ..s;lrd.;Crettaz, R. Heterocycles,
-0
; Noyori, R. Clieni. Cornmun., 1999, 1235
CO2Et
99%
1999, 51, 2589.
Related Methods: Section 25 (Acid Derivatives fromHalides).
SECTION 116: ESTERS FROM HYDRIDES This section contains examples of the reaction R-H (R = alkyl, a v l , etc.).
-t
RC02R' or R'C02R
0
65% chiral hipyridine , 2 ddiol
Lee, W.-S.;
5% [C'u(MeCN)d] BF,
aOxPh
u; Chan, 11.-L.; Choi, W.-W.; Ng, L.-Y.
Tetruliedron Asyrnnt., 2001, 12, 1007.
57% (52% ee, R )
Section 116
Esters from IIydiides
0
329
1%KuCl3-n NzO, MeC0GI TFA,DCM,rt,4h
li
Ph
77% Chern. Corninun., 2001, 65.
-
Komiya, N.; Noji, S . ;
Ley
1 . TI(OTfh , DMF , 6 0 T 2. H Z 0
Ph
*
&
94%
0
h
Lee. J.C.; Jin, Y.S.; Choi. J.-11. Cheni. Conzrmn., 2001, 956.
C0,B n
13%
C02Bn
,30"C,8h
0 . 1 sc.(o,soc~,z€~~5),
*
81%
0 -
Tetrolzerll-on Lett., 2000, 41, 3107.
Mori, Y.; Kakumoto, K.; Manabe, K.; PhCO,r-Bu , 5 % C u ( 0 T h 7.5% trk(oxazo1ine) ligimd acetone, 0°C , 2 d
Ph 80% (83% ee)
Kohmura, Y.; Katsuki. T. Tetruldrnn Lert., 2000, 41, 3941.
S t Q ,A%O, 0,
J-( f
reflux, 12 h
Koltun, E.S.; Kass. S.R.Synthesis, 2000, 1366.
(I9
(84
Akhrern. I.; Orlinkov, A.; Afanas'eva, L.; Pelrovskii, P.; Vitt, S. Tetruhedron Lttc., 1999, 40, 5897.
1)
36%
16) <7%
330
Section 117
Compendium of Organic Synthetic Methods, Vol 11
*c
Also via: Section 26 (Acid Derivatives) and Section 41 (Alcohols).
SECTION 117: ESTERS FROM KETONES engineered E. coli cells
61% (>98% ee)
Me
Me
$
II
eo
Mihovilovic, M.D.; Chen, G.; Wang, S.; Kyte, B.; Rochon, F.; J. Org. Cheni., 2001, 66, 733. 1 '31(3,S-di-CF3-GH3S e h _
2 q 60%)H 2 0 2 , CF3CHzOH 20T, 1 h ten Brink, G.-J.; Vis, J.-M.; Arends, I.W.C.E.;
<
90%
J. Org. Chem., 2001, 66, 2429.
CO2Me
p h d o 9 9 0 % (3% ee)
, 2 q slnIz, THF
chirul proton souice -78°C-10°C Ph XU, M.-H.; Wang, W.; Xia, L.4.; Lin, G . Q . J. Org. Cheni., 2001, 66, 3953. Ph
Ph
SO% MgIz, 50% R-BINOL, -25°C CI12ClI, PhCMqOOI? , 8 h
*
Ph+O
h,,*\+'"
Go 65%
C0
Bolm. C,; Beclanann, 0.;Cosp, A.; Palazzi, C. Synletf, 200Z, 1461.
I1202
, Ph-As03H2
-
85%
(CF3)2CIIOH, 240 min
BerkessL1.;Andreae, M.R.M. Tetrahedron Lrtt., 200Z, 42, 2293. ..>
H0
1. S-BINOL-AIMqCl hexandtoluene, rt
*
0'
2. cuinene hydropaoxide #* Ph -25°Cit Ph Bolm, C.; Beckmnnn, 0.;Palazzi, C. Cun. J. Client., 2001, 7Y, 1593.
71%
33 1
Esters from Ketones
Section 117
*Do
Ph Et,Zn ,c h i d amino-abohol toluene, -78°C
-
-26°C
75% (39% ee)
Shinohara, T.; Fujioka, S.; Xotsuki. ff. Heterocycles, 2001, 55, 237.
1
HNO, ,M d H qumt
SiMe 2h *PhO'Me Ph Patrocinio, A.F.; Moran. P.J.S. Synfh. Crinimun., 2000, 3 0 , 1419.
po,"b 1) LiSnMe, 2)& , BF,eOEt, -7X"C, 1 h
3. Pb(OAc)4, C a m 3 4. 112 ThCI(PPh,),
. .; Wang, Q.; Halford, B.A.; Elias, J.S.; Maxwell, J.P. s e Tetruhedron Lxtt., 20110, 41, 9655.
(85
IIamed, 0.;El-Qisairi, A.; b
y
.
0-o
polymer-supported peroxyacid
*
15) 73%
Po
PA& Tetruhdron Lett., 2000, 41, 3021.
68%
Lamhert, A,; Elings, J.A.; Maccjuarrie, D.J.; Cam, G . ;C l a r k . S y n l e t t , 2000, 1052.
ji
Ph
CIO,Me
cut Ru,(CO),, , ethylene 5 atin CO , toluene , 160°C
P(4-CF3-C6114b, 2 0 h
94%
*h4azc+
Chatani, N.;Tohisu, M . ; Asaumi, T.; Fukumoto, Y.; Murai. S. J. Am. Chcnt. Snc., 19Y9, 121, 7160.
0
332
Coinpendiuiii of Organic Synthetic Methods, Vol 11
Section 119
3M H 2 0 2 , ether, rt a t MeReO3,l h
Phillips, A.M.F.;
6) 80%
(94 Eur. J. Org. Cheni., 1999, 1767.
(96
4) 90%
Kotsukl.; Arimura, K.; Ariiki, T.; Shinohara, T. Synlrtr, 1999, 462. REVIEWS : "100 Years of Beeyer-Villiger Oxidations,"Renz, M.;Meunier. E Eur. J . Org. Cliern., 1999, 737. Also via: Section 27 (Acid Derivatives).
SECTION 118: ESTERS FROM NITRILES NO ADDITIONAL EXAMPLES
SECTION 119: ESTERS FROM ALKENES C O , autoclave, 6O"C, MeOII
Pd(lI)catalyst , phosphine ligand
C C O 2 M e
81% Pugh, R.I.; Drent.; Pringle, P.G. Chorn. Coinniun., 2001, 1476.
A
c4H,
PhIO , 2 eq Me,SiS03C1
Bdssinddle.; , .. . Katainpe, I.; Maesano, M.G.; Tetrulicdron k t t . , 1999, 40, 7417,
t
+x 19%
Eso2 68%
c3H7
Patel, P.; Taylor. P.G.
0
Section 120
Esters from M i x .
333
1. 1 atmCO. THF
... Takimoto, M
2. q HCl
.
i
96%
m J . Anr. Clieni. SOC., 2001, 123, 2895.
0, , hexane , reflux
-50°C
+
0°C , 5 min
0
35%
32% Barrero. A.F.; Alvarez-Manzaneda, E.J.; Chahhoun, R.; Cuerva, J.M.; Segovia, A. Synlett, 2000, 1269.
80°C Pd2(dha)3/chiral 800 psi O H , , phosphine
M
e
V
Ir
CHZCI;?, 1 d
87% (95% e e , R ) 0
Cao, P.; Thanv X. J. Ani. CIi~ni.Soc., 1999, 121, 7708. Also via: Section 44 (Alcohols)
SECTION 120:
M5Si
*F
ESTERS FROM MISCEI,I,ANEOUS COMPOUNDS
PhSH , PhH , -78°C Chinchona alkaloid catalyst
MqSi
SPh
PhP C = O Ph Blake, A.J.; Friend, C.L.; Outram, R.J.; Simpkins. N.S.; Whitehead, A.J. Tetr-uhedronLr.tt., 2001, 42. 2877.
AcCl , Sm/cat CoC12, TI IF P h.% Se Ph Chen, R.; 7,hang. Y. Syntlz. Cnrnniiin., 2000, 30, 1331.
*
PhSeAc
97% (91% ee)
79%
Section 120
Compendium of Organic Synthetic Methods, Vol 11
334
QBn =
,,,.+'' 11111111111
incpha , 4 h
OBn 4-
,% ,",
DCM , r t
0
1) 70%
(4 Hunt, K.W.; Grieco. P.A. Org. Lett., 2000, 2, 1717. 1. 5 eqBu3SnI-I, 0.5AIBN PhH , reflux
2f
2 . Jones =agent
Merrifield resin-/l--0 Watanahe, Y.; Ishikawa, S . ; Takno, G.; PhSSPh
36%
0
Tetmherlron Lett., 1999, 40, 3411.
I.I'Bu3 , H , O , D M F , l h b
2
PhS
2. Ac20, 1 h
ji,,
95x9746
Ayers, J.T.; W r s.on. S'.& Synth. Cnnitizrtn., 1999, 2Y, 351. SMe SMe
BF3.OEt2, H2S, IefluX dioxane ,4h
Ph 67%
Nair, S.K.; Askoknn, C.V. Synth. Comnzun., 1999, 29, 701. PhSSPh Chen, R.;
P hSe Se Ph Liu, Y.;
AczO, Sm/cat CoClz
PhSAc
t
TI-IF , S O T , 4 h Synth. Corrzrrirtn., 1999, ZY, 3699. BzCl ,SidCiCl, ,TIIF, rt
75%
*
PhSeBZ
70%
Syntli. Conirrzun., 1999, 29, 4043.
REVIEWS : "Carhoxylic Acids and Esters," J;ranklin, A.S. J. Chent. Sor., Per-kin Truns. I, 1999, 3537
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 9 PREPARATION OF ETHERS, EPOXIDES AND THIOETHERS
ETHERS, EPOXIDES AND THIOETHERS FROM ALKYNES
SECTION 121:
=
t-Bu
t-Bu
1 . SzC1,, CII,cI,
t-Bu9v'
* Cl 2. distil Nakavama. J.; Takahashi, K.; Watanahe, T.; Sugihnra, Y.; Ishii, A. Tetruhetlron k t r . , 2000, 41, 8349.
SECTION 122:
t-Bu
56%
ETHERS, EPOXIDES AND THIOETHERS FROM ACID DERIVATIVES NO ADDITIONAL EXAMPLES
ETHERS, EPOXIDES AND THIOETHERS FROM ALCOHOLS AND THIOLS
SECTION 123:
B F3 .OEtz
I
OH IIardouin, C.; Tnran, F.; Doris.
0
,
\ O /O
N
/
P 11
I
E J. Org. Chetti., 2001, 66, 4450. I
Me1 ,5Maq NaOII * O cat Me(CJll7)&CI
I.J.V.; Mailleux, I. Synfh. Corirttrun., 2001, 31, 1.
z
97%
Ii N
O
O
\ /
M
e
90%
336
-2+y
Coinpendiuin of Organic Synthetic Methods, Vol 11
Section 123
E. M : p, 25”C, z c ~240~ho
HOf
Ph
m. T.-P,; Hu, Q.-Y.; Ma, I,.-T. J .
Ph
Aiiz.
Ph
Cltein. Soc., 2001, 123, 2450.
2% Pd(0Ac)z , 1.5 eqCs2C03 cat chkal hinaphthyl ligand , toluene 50”C, 26 h
Kuwabe, S.-i.; Torraca, K.E.; Buchwald. S.1,. .I. h
i .
Cheni. Soc., 2001, 123,
82% 12202.
acetone, 4 ” C , 1 d
H ”0 Guiso.
D
-
I
TsOH
*I 1 0
/
m; Marra, C.; Cavarischia, C. Tctruhedron k , t t . , 2001, 42, 6531.
0.Y.;
Synth.
I
Mihara, M.; Hayakawa, N.; Miyata, T.; Kaneko, Y.; Miyata, T. 31, 439.
Coniiiiun., 2001,
OAc
4%)Pd(dha)2, (+)-DPPIO
MO
T H F , rt
*
IOTB,I’PS ” &’
98% (8 1 :19 cis:truns) TB‘IPS-0 JIara. 0,; Fujii, K.; Ilamada, Y.; Sakagami, Y. Hr,terocyclcs, 2001, 54, 419.
63%
Section 123
Ethers from Alcohols
(4-Me-C6114)I+BF4-,THF ,rt
PhSI1
337
P~S(~-MLC,H~)
e
cat Pd(PPh3)4 , NaZCO,
95%
Wang, L.; Chen. 2.-CSyntlz. Conintun., 2001, 31, 1227.
quant (97:3 trunsxis) SolladiC-Cavallo. A,; BouCrat, L.; Roje, M. Tetrcll?etlronLcjtt., 2000, 41, 7309. 1. PhBr , PPh3 , DEAD TNF , rt
p
2. BuLi, TIIF -50°C --+ rt
Ph
A,
*
a
P
h
10% McN(NTf)z, DCM, 21°C
Ph 0.2M, 0.5 h Ooi, T.; Ichikawa, H.; Itagaki, Y.;
'hPI'h'O' Heterocycles, 2000, 52, 575.
>%%
c1 I'hCIIO ,hC13 , SnC13 DCM, r t , 4 h
Hi>terocycle.s, 2000, 53, 1691.
Li, J.;
C ) - ( p - N = + N G
(CH2112
I
011
DMAP, DMAP-IICI, CHCI,
34% cis (8% truns)
Ph
(cHu
77% (+ 13% diolide) Keck. G.E.; Sanchez, C.; Wager, C.A. TclruherIron kjtt., 2000, 41, 8673.
c,eSH
338
Compendium of Organic Synthetic Methods, Vol 11
Section 123
PhI, cat CuBr ,toluene
\ /
=flux, 1-4h
Palorno.;Oiarhide, M.; Lbpez, R.;G6mez-Bengoa, E. Tetruhedron LEtt., 2000, 41, 1283. P~IB(OH)Z,1.5 CU(OAC)~* P S DMF, 3 eq Py , MS 4,4 reflux ,3 h Herradura, P.S.; Pendola, K.A.; Guv~.R.K. Org. Lett., 2000, 2, 2019.
0
2
N
0
0
M q S 0 4 , NaOH , 8 h PEG-400, heat
H
:
O
-
B uBr , CsOH ,I B A I
ph
Ph
SH
88%
N
O
O
M
-0Bu
Ph
MS 4 A . DMF ,23"C, 10 h
Dueno, E.E.; Chu, F.; Kim, S.-I.;
h
95%
Cao. Y,-0.; Pei, B.-G. Synth. Cornniun., 2000, 30, 1759. -011
z
P
92%
K.W, Tetruhedrnn Lett., 1999, 40, 1843.
PI,-
OH
P M 3 , ADDP , h - H
* Ph-s-I-ll 79%
ADDP = l , l ' ( a z o d i c ~ l ~ o n y l ) d ~ i ~ r i d i ~ i e Falck. J.R.; Lai, 1.-Y.; Cho, S.-D.; Yu, J. TetrulicJdronLett., 1999, 40, 2903.
X
, LiCD,MeN02
Montmorilloni telH20 l.t.2d Chlbl.;Hiram, T.; Kitano, Y.; Tnda, M. Chent. Contrnun., 1999, 691.
>99%
i-PrOH , zeolite-KMnO, Ph
*
OH
DCE, rt , 3 0 inin
Ph
oi-fi
9wo Gadhwal, S.; Boruah, A.; Prajapati, D.; Sandhu. J.S. Synth. Co/nmun., 1999, 29, 1921. PhSII
1 . Et,NIICl, MLCN , It, 15 min
2. EtI , overnight I'eroci, M.; Inesi, A.;
*
Ph-SEt
Sywth. Contnrun., 1999, 29, 261 1 .
93%
e
3 4
Section 124
339
Ethers from Aldehydes
,e- , A L ~ I I
97%
/
3M LiClO4, M e N q
OMe
bPh
OMe G i h a . K.; Fukuda, M.; Kim, S.; Kitano, Y.; Tada, M. J. Org. Chem., 1999, 64, 7654.
c ~ I ~ e , ; ~ ~ & p h
70%
Me0 Valenti. P.; Belluti, P.; Rampa, A.; Bisi, A. Synth. Cornriiun., 1999, 29, 3895.
P
h
o
\ /
O
BnBr , Cs2CO3 , DMF* P
H
h
e
\
O
B
23T,1h Synrh. Corririiun., 1999, 29, 4423.
Parrilsh, J.P.; Sudaresan, B.;
n 92%
1 . Mg , I2 , 1EflUx
* P hCH20CII2P h 80% 2. Tf*O,5"C Nishiyama, T.; Kalneyama, H.; Maekawa, H.; Watanuki, K. Cun. J. Chem., 1999, 77, 258. PhCIIzOH
SECTION 124:
ETHERS, EPOXIDES AND THIOETHERS FROM ALDEHYDES
Me1".C)-
P hCI 1 0
Me
, B n Br
, NaO I-I
t-BuOII , € 1 2 0 , 2 d
Zanardi, J.; Leriverend, C.; Aulwrt, D.; Julienne, K.;
J. Org. Cheni., 2001, 66, 5620.
PhSeSiMe, , PhH
*
4
&
h".
Ph
PhCH20SiMq 78 % Bu,SnI-I , cat AIBN XOC , 1 X h Kajiinoto, €1.; Kotani, K.; b c l a. N, Org. Lift.,2001, 3, 3087.
P hCI-IO
.. . . . m;
/
92%
Section 124
Compendium of Organic Synthetic Methods, Vol 11
340
M e 0 6)=Nz
PhCfIO
, 1% Rhz(OAc)4
DCM
*
Pha \
Dovle. M.P,; Hu, W.; Tinunons, D.J. Org. Lett., 2001, 3, 933.
Phff I 0
ph %,/
s,,,
66%
Ph
54% ( 9 4 5 &cmr:cis) 5%eeSS
W 0 3 ,r t , CHzClz Saito. T,; Akihu, D.; Sukairi, M.; Kanazawa, S. Tetruliedron Lett.* 2001, 42, 57.
MeCHO 0.1 M , hv, PhII * : H
+Ho>%
%%
19)
(8 1 eck. A.G.; Bondock, S. J. Am. Clic~m.Soc., 2001, 123, 6191. QSiEt3 -Rh catalyst, NSiEt, * o \ , \ , , , \ \ c o z M e C02Me
+
QSiEt,
O
P
0
2
toluene, 50°C
+
1) 2)
81% 81%
3. aq I I c l Teng, X.; Wada, T.; Okamuto, S.; Sato. F, Tetruliedron Lett., 2001, 42, 5501.
74%
RhCI(PPh& (3 Rh€I(PPh3)4 (1 Emiahata-Smith, D.; McKillop, A,; Mills, C.; Motherwell, W.B.; Synlctt, 2001, 1302.
+
M
e
Section 124
Ethers from Aldehydes
PhSH ,p-TS0I-I P 0. Y,;
I
0
Mihara, M.; Kawai, 1-1. Synlett, 2001, 1317.
341
q
54%
SPh
In(OTf)3, DCM ,0°C
h ( O T f ) ,, DCM Ptl-
95% (6.535 truns:cis)
CHO
40°C Ph b h . T.-P.; IIu, Q.Y.; Tan, K.-T.; Cheng, H.-S. Org. k i t . , 2001, 3, 2GG9.
Ph
/tPh
OsO, , K3Fe(CN), , K2C03 polymer-bound DIIQD-PHAL
Ph
t-BuOII, I120 , 0°C , 1X h
01r
92% (99% ee) Federov, A.Yu.; Cairara, F.; Finet. J.-P. T m a l i d m n Lett., 2001, 42, 5875.
72% Concellon, J.M.; Cuervo, 11.; Fein&ndez-Fano,R. Z'ctruhcciron , 2001, 57, 8983. PhCHO
PhCH=N-NTs- Na',
1% Rh2(0Ac\c4
20% tetrahydmthiophene , MLCN 20% BnNEt3CI,4O"C , 3 h
.r
A
ph
"I..,
Ph
95% (>98:2trunsxir) Almso, E.; I-Iyund, G.; Lydon, K.M.; Palmer, M.J.; Porceiloni, M.; StudIey, J.R. Angew. C h m . Int. Ed., 2001, 40, 1430.
;.K.V-
342
Section 125
Compendium of Organic Synthetic Methods, Vol 11
Me . I
92%
OMe
YrldrlY.; . , Reddy, B.V.S.; Kao, T.P. Tetruhedrnn L.ett., 2000, 41, 7943. PhCI-10 ,TIIF, r t , 3 d
m S i M e ,
i-Pr,
0.2
i-Pr
( Jy-pr N-PYIIIN: \,\ti'\
Wang, Z.; Kisanga, P.; w
PhCI10
e
*Amp 74%
a;x
. .I.G. J. Org. Clicm., 1999,64,6459.
Me$i-SnBu3
(8:l)
/
Ph
InCI, ,DCM Viswanathan, G.S.; Yang, J.; ]Li. C.-J. Org. L.ett., 1999, 1, 993.
(Jy --chr
4 q B n B r , O C , MeCN 2.8 eq NaOH , 2 1 h
l'm#l,
'"'F
PI1
ph
78% (92%ee)
Ph
Synlett, Z999, 1388.
IIayakawa, R.;
,,d"
P hCI 1 0
S
, 2 eq BnBr , 2 eq KOII MeCN-II20, rt , 1 d
-
Ph\,,\\\*'\ 92% (88% deB4% ee)
Julienne, K.;
SECTION 125:
1.
; Henryon, V.
J. CIWX SOC.,Perkin Truns. 1, 1999,731.
ETHERS, EPOXIDES AND THIOETHERS FROM ALKYLS, METHYLENES AND ARYLS NO ADDITIONAL EXAMPLES
Section 127
Ethers from Arnines
SECTION 126:
)(
Me
N,C021-Bu
343
ETHERS, EPOXIDES AND THIOETHERS FROM AMIDES
PhCHO , hv ,M C N
I
*
5h
Bn
RMe
Ph
N(Bn)COg-Bu
70% (2971 cis:truns)
Bach. T.; Schriider, J. Synthesis, 2001, 1117.
5) 58% conversion
(95
I\dam.;Stegmann, V.R. Synthasis, 2001, 1203.
PhCfIO
)==(
OlBDMS SePh
hv , MeCN
*YPh
OTBDMS SePh
81% ( 6 2 3 8 truns:cis) 80% conversion
Al.e.;Tachibana, K.; Fuji~noto,K.; Nojima, M. Synthesis, 2001, 1243. SECTION 127:
ETHERS, EPOXIDES AND THIOETHERS FROM AMINES
M5CI ICI-12C€120N0 MeZS2, MeCN
-
NO2 Allnire, F.S.; b y g a . J.W. Synth. Corrzrrrun., 2001, 3 1 , 1x57.
6 SMe
NO2
57%
344
Coiiipendiuin of Organic Synthetic Methods, Vol 1I
rBuOK ,b-BuOIf
Section 128
Ot -Bu
*
82%
IEflux
; Rajaiah, G.; Chandraiah, L.; Swamy, D.N. Synlert, 2001, 1779.
SECTION 128:
ETHERS, EPOXIDES AND THIOETHERS FROM ESTERS 1% [RuCIZ(CO)~],, EtI , 16 h 5% Et,NII, toluene, 100°C
OSiEt, 57%
Et,SiH * dOMe Terruheclrnri Lett., 2001, 42, 2149.
dOMe Igarashi, M.; Mizuno, R.;
-
OMe TiCh , TMSOTf, E1,SiI-I
ph? Yato, M.;
. 0
PhO -Me 0 DCM ; Ishida, A. Tetmhedron, 2001, 57, 5353. 1. i-BuZNII 2. PhSeH, Bh-OEt,
81%
SePh
91% (85:15 trunscb)
3. H Z 0
Schmitt, A.; Reissie. H.-ULSyrithc,sis, 2001, 867.
OCOzMe I
1. PhOH, THF Nd4MDS
PPh
1) 96% 1. Ph3SnII, PhZSA2, rt 0.5 BEt, , 1 h
2. N B N , 110°C MeO Ph D.0,; Song, S.H. Synlcrr, 2000, 811.
*
cat Cp*RuCl(cod) ,McCN BUSH,rt , 1 h
M e 0-Ph
94%
//\/SBu moCoZMe *
Kondo, T.; Moiisaki, Y.; Uenoyama, s.-y.; wada, K.; msudo. T,-~. J . Ani. C h n i . Snc., . l Y Y Y , 121, 8657.
97%
Section 129
Ethers from Ethers
Ph
345
2.2 ~q P h j S d I , rt BEt3 ,toluene 30 inin
97%
@?h
ee. DJ.; Leach, J.D.; Setiadji, S. TerruAerlron, I Y Y Y , 55, 2847.
SECTION 129:
ETHERS, EPOXIDES AND THIOETHERS FROM ETHERS, EPOXIDES AND THIOETHERS
A0
c IOII21
MqSiCl, hexane, 2 h sec-BuLilchiral diiunine -90"~- - 5 0 " ~
t
c 10%
/&jiMq 1
73%
Ifodeson. D . K ; Norsikian, S.L.M. Org. Lett., 2001, 3, 461.
CO,CMeCy, 1% CuOTf , EtOAc , rt 1.1%J S, S-his-fell-ocene heterocycles Lo, M.M.-C.; Fu. G . C , Tetrulic~clron, 2001, 57, 2621.
ph
Ph2CH-OMe
C J I P H , Fe(C104)7
7496484: 16 cis:truns)
*
Ph2CHOC3H7
97%
reflux, 150 inin
Salehi.;Irandoost, M.; Seddighi, B.; Behhohani, F.K.; Tahmasebi, D.P. Synth. Coniriiun., 2000, 30, 1743.
PhS
w
I-(CI12)s I , NaNI12-DME
0°C , 2 h
-
75%
Choppin, S . ; Gros, P.; Fort. Y. Syntlz. Conirnun., 2000, 30, 795. I'
1. 1.5 ec1 BuLi, 'I1IF ,-78"C 2 . 3 eq L i c l ,-78°C ..-, 0°C
5 Ph
Komine, N.; Tomooka. K.:
Hetemcyrles, 20011, 52, 1071.
63% (86:14 truns:cis) S.574 ee 1 for hob
346
Section 129
Compendium of Organic Synthetic Methods, Vol 11
m S i M e 3
,-5o*c
SnQ. CI-IzClz
OBn
79% (1:l &:trans)
a; Kimura, Y.; Yokie, I. Tetruhedron Lett., 1999, 40, 5877. M
e
\ 0/
\e /
M%CCH,I, TIIF,2 eq EtMgBr rt , 5 h * M
0 MgBr
Inoue, A.; Shinokubo, H.;
SiMq
w
76%
Synlett, 1999, 1582. TMSN3, PhH
o
os
Mn den-iinrnol~ilizd inesoporous meterial Kantarn.;Choudary, B.M.; Barathi, B. Syntlz. Conimun., 1999, 29, 1121. 0 . 2 Sn(PPh3)(ClO4)z ,MeCN* (NHz)2CkS,reflux , 4 5 min
93%
; Mirkhani, V. Synth. Conimun., 1999, 29,
EFIo
2.5
Ph\/\/
S d 2 , THF-HMPA
*
2.5 eq TES-CI
IIonda.;Ishikawa, F. Syntlt.
Ahe.;Koshiha, N.; P
h
q
oor. N... T;-.
o
.
2079.
Contntun., 1999, 29, 3323.
Yamasaki, A,;
OSiEt,
ph\/\/
97%
eterocycles, IYYY, 5Z, 2301.
NHJCN , P4VP-Ce(OTf)4
*
P h q s MtCN ,i t , 15 inin Shekuiriz, M. Syntlt. Cornmim., 1999, 29, 3313.
90%
Section 130
Ethers from Halides
341
REVIEWS: "The Brook Reanangement In Tandem Bond Fonnation Strategies," Moser. W.H. Tetruhedron, 2001, 57, 2065.
SECTION 130:
B
e
C
Parrish, C.A.;
ETHERS, EPOXIDES AND THIOETHERS FROM HALIDES AND SULFONATES NaOt-Bu ,cat Pd(OAch, 100°C toluene , phosphine ligand
l
B
\u /
92%
J. Org. Client., 2001, 66, 2498.
'
O Or-Bu
BuOI-l, 2%Pd(OAc), 2.S% phosphine ligand toluene, 2.5 eq Cs2C03 Torraca, K.E.; Huang, X.; Punish, C.A.; Bchwald. J. Am. Chem. SOC., 2001, 12.3, 10770.
a
NMP ,70"C, 6 h 88%
NO2
Gujadhur, R.;
oc"'
Synth. Comnzim., 2001, 31, 2865.
- &Q
1. i-PrMgBr, T I I F , -10°C
2. PhCIIO ,-10°C
reflux
/
Ph
82%
Delacroix, T.; BCrillon, I-.; Cahiez. G.; Enochel. P. J. Org. Clietn., 2000, 65, 8108.
C S 2 , NaBH,, TIIF Wan, Y.; Kurchan, A.N.; Barnhurst, L A . ;
Org. Lett., 2000, 2, 1133.
Section 132
Coinpendiurn of Organic Synthetic Methods, Vol 11
348
PhSeSnBu:, , toluene, 80°C 5% Pd(Ph3), * Tokunaga, K.; Sonod a. N. Org. LEtt., 1999, 1, 1725. Related Methods: Section 123 (Ethers fmm Alcohols).
SECTION 131:
ETHERS, EPOXIDES AND THIOETHERS FROM HYDRIDES NO ADDITIONAL EXAMPLES
SECTION 132:
ETHERS, EPOXIDES AND THIOETHERS FROM KETONES
Kang, T.; Scheffer. J.R. Org. Lett., 2001, 3, 3361.
d
PI
Ph Ma, Y.;
PI1
85%
Ph
Sin12, S i n , it , 2 0 inin
Ph
Ph
s; Chen, .I. Synthesis, 2001, 1004. C&I ITOH, Pd/C , Hz s t E m 105°C
Chent. Lett., 2000, 926.
Fujii, Y.; Furugaki, H.; Yano, S.;
[t-BuSiMezCFBrzA3uLi]
*
Ph
THF
97%
r-BuMe,Si
. . -M.;IIata, T.; Hiyama, T. Heterocycles, 2000, 52, 707.
94%
Section 1.74
Ethers from Akenes
CHCI, , NaOII , TEBA
349
+I:
Ph Ph
z
Ph&Ph b s t e li. '; Romaliski, 1.; Swiatek, A,;
80%
H d v . Chirn. Actu, IY99, 82, 946.
Related Methods: Section 124 (Epoxides from Aldehydes).
SECTION 133:
ETHERS, EPOXIDES AND THIOETHERS FROM NITRILES NO ADDITIONAL EXAMPLES
SECTION 134:
ETHERS, EPOXIDES AND THIOETHERS FROM ALKENES ASYMhlETRIC COMPOUNDS 2
O X O W, 4 eq NaZC03
chir al a inm)nium s3 It -alcohol MLCN/I1,O
64% (30%ee)
; Rassins, G.A.; Bairos, D.; Ardakani, A,; Buckley, B.; Bethell, D.; Smith, T.A.D.; Slawin, A.M.%. .I. Or&#.CIWIK,2001, 66, 6926.
A
4 '
[ R ~ ' ~ ( D ~ - € t i r * ) C,lPhH, ,] rt
* 75% (70% ee) Sol-Gel-silica , 2 d I'h Zhang, R.; Yu, W.-Y.; Wong, K.-y.; Che. C.-mJ. 01-8.Chwz., 200Z, 66, 8145. Ph
w
Ph
Cr salen catalyst , PhIO Ph3P0
A0
Ph
,\\"
,,+"
4S% (92% ee)
Daly, A.M.; Renehan, M.F.; Gilheanv. D .G, Org. Lett., 2001, 3 , 663.
--/
Ph7
Cr-salen coinnlex 0°C MeCN, Ph;P=O
''I,,,
72% ee '4,
O'Mahony, C.P.; McGanigle, E.M.; Renehan, M F . ; Ryan, K.M.; Keirigan, N.J.; Bousquet, C.; y. D.Cr, or& k t t . , 2001, 3, 343s.
350
Compendium of Organic Synthetic Methods, Vol 11
Section 134
0.1 r-BuCHgIIO , 3 h , it
0.1 bis-amidopyrrolkline
/
Ph
MtCN ,NaHC03 , H 2 0
Ph 93% (65%ee) 80% conversion Org. k t t . , 2001, 3 , 2587.
n; Ho, L.-M.; Zheng, Y.-S.; Ho, C.-Y.;
Lh * L 5% (R) Ln catalyst TBHP - d ~ i ~ ~ e
Ph
99% (96% ee)
, , , , #$
MS 4 A , TIIF, 25 nun
Nemoto, T.; Ohshima, T.; Yamaguchi, K.; Shihasaki. J. Am. Cheni. Soc., 2001, 123, 2725.
Ph
Ph
M,
-a
1.20% La-S-BINOL-O=AIPh3complex 2.4 eq TBHP , toluene, T H F
dN kN4
Ph
2.MeOH
MS4.4,lt
& =
Q
O Me
Ph
86% (91% ee)
Nemoto, T.; Ohshima, T.; Shihasaki, M. J. Ant Cheni. Soc., 2001, 123, 9474.
A
Ph
Mn salen catalyst , NaOCl CH,CI, , Na,IIPO, (pH 11.3) 4-phenyl pyiidine N-oxide
/
Ph
53% (65% ee ,R )
Bhn, K.41.;Park, S.W.; Choi, S.; Kim, H.-J.; Moon, C.J. Tetrahedron Lett., 2001, 42, 2485.
Mn salen complex , PyNO CNzCl2, 5.5 h
Kureshv. R .L; Khan, N.H.; Ahdi, S.H.R.; Patel, S.T.; Jasra, R.V. Tetruheriron h i t . , 2001, 42, 2915.
quant ((5%
f!e
,RS)
UN~I-I~~OZ ,DBU 1Wh
Ph immobilized poly-Lleucine on polystyrene
Bentley, P.A.; Bickley, J.F.; Roberts-;
76% (84% ee) Steiner, A. Tetrahedron Lctt., 2001, 42, 3741.
Section 134
Ethers from Alkenes
fllIcp */
o””
w
Ph
L L
Shu, I..;
35 1
0
+
0
IIzO,, MLCN , KZ(30, EDTA , 0°C , 12 h
&
Ph
93% (92% ee)
Tctruheclron, 2001, 57, 5213.
;9p
cunene hydiuperoxide , THF
Ph ph 5% BWOL catalyst Ph Chen, R.; Oian. C.: de Vries. J.C. Tetruhedron, 2001, 57, 9837.
Ph
Ph
(82% e e , R,S)
MePhCH-OOII , toluene, 0°C 10% chiral phase transfer catalyst *
p hhPh
Adam.;Rao, P.B.; Degen, 11.-G.; Saha-Mvller, C.R. Tetruheclron Asyinni.,
4
Ph
UIE*€I~O~ ,DCM ,MeOH ditneric Mn-salen catalyst
t
/
Ph N I I ~ O A C6, h Kurtshv.;Khan, N.11.; Ahdi, S.H.R.; Patel, S.T.; Jasra, R.V. Tctrultcrli-onAsyirint , 2001, 12, 433.
-
62% ee ,S,R)
200Z, 12, 121.
68% (23% e e , R)
1.
&ph
Ph
mesoporous silica, Os04 Cinchona a l k a k d ,O“C , 1 d
Ah
Ph Bortolini, 0.; ; Fantin, G.; Maietti, S.; Medici, A. Tctruhcdron Asyii~in.,2001. 12, 1113.
Ph
Ph
mesoporous silica, OsO, Cinchona alkaloid ,0°C , 1 d
Lee, 1I.M.; Kim, S.-W.; weon. T.:
A
Ph
;-
qumt(99%ee)
/am
* Ph quant(99%ee) Tetruheclrnn Asyrnni., 2001, 12, 1537.
OXOW, NaIICO3 , aq Naz(edta)
MeCN , chiral ketone, rt , 1 d *
f i d O quant (48% ee , R) Moss, W.O.; Reeves, J.R. Tetruherlron Asynm., 2001, 12, 2779.
Section 134
Compendium of Organic Synthetic Methods, Vol 11
352
p3-Leua-Leu-R, aq NaOII, DBU Ph
toluene , THF , urea-I1202 1 d
Ph
PhhPh 92% (70% ee)
Coffey, P.E.; Drauz, K.-11.; Robe&.-SM ; Skidmore, J.; Smith, J.A. Chern. Comnrun., 2001, 2330. U R + I I ~ O,~DBU 190 h Ph
immobilized p l y - L - * &Ph leucine on polystyrene
/
76% (84% ee) Steiner, A. Tetruherlron Lett., 2001, 42, 3741. Bentley, P.A.; Bickley, J.F.; fioherts. S.M.;
0--a \ /
,ether, rt , 6 h
a
1.2%Ru-salen catalyst
% ,,
57% (84% ee)
f
0
Nakata, K.; Takeda, T.; Mihara, J.; IIamada, T.; Irie, R.; Katsuki. T. Chem. Eur. J., 2001, 7, 3776. Oxone, dioxane , N&IC03
*
chiral cyclic diunino-ketone
Ph-
Q+,
Ph 71% (70% ee)
Matsumoto, K.;
Heterocycles, 2001, 54, 61s.
Oxone , chiral ketone
A
Ph
K2C03, DME-DMM
A0
* Ph
quant (81% ee)
Tian, H.; She, X.; Xu, J.;
Org. Lttt., 2001, 3 , 1929.
AN* bN
Ph
*A
1. 20% I,a-S-BINOL-O=APh3 complex 2.4 TB HP , toluelle , THF
MS 4 A , rt
2.MeOII
,,#
Ph
Nemoto, T.; Ohsirna, T.; Shihasaki, M. J. Ain. Cli~~rn. Soc., 2001, 123, 9474.
OMe
86% (91% ee)
353
Ethers from Akenes
Section 134
B t % c h CqEt
AA
cat O,
,O
Mg
,t-BuOOH
* ~ 5#''4 % ( 7 5 % )
Bu MS4Aq,2h Bu Jacques, 0.;Richards, S.J.; Jackson.R.F.W, Chenz. Conirnun., 2001, 2712. VO( Oi-Pr)3 , toluene ,-20°C
chiral hydroxamic acid ligand
&
IIoshino, Y.; Murase, N.; Oishi, M.;
OH
96% (91% ee) Bull. Clieni. SOC.Jpn., 2000, 73, 1653.
E. cnli JM109 (pTAB19) >99% ee.
Bernasconi, S.; Orsini, F.; Sello. G.; Colmegna, A.; Galli, E.; Bestetti, G. Tetruhedrnn Ixtt., 2000, 41, 9157.
99% (51% ee) Adam. W.; Rao, P.B.; Degen, 11.-G.; Saha-Moller, C.R. J. Am. Clzeni. SOC., 2000, 122, 5654. polymer-bound chiral Mn(III)-sden complex NaOCl , DCM, 0°C: 4-Ph-pyridine N-oxide 90% (95% ee)
Roh, E.J.; Yu, B.M.; Chi, D.Y.; Kim, S.C.; Lee, K.J. Chem. C~inrnrrn.,2000, 6 15.
;-
Oxone, KzCO3, DMEDMM p1-I 8 buffer, -10°C chiral dioxirane
87% (91% ee)
Tian, H.; She, X.; Shu, L.; Yu,H.; 3u-X J. Ant. Cheni. SOC.,2000, 112, 11551
354
Compendium of Organic Synthetic Methods, Vol 11
Section 134
2% Mn-salen complex, phI0
&ph
Ph
A
m
* Ph
PhCl ,0°C
82% (66% ee)
.
Nishikod, H.; Ohta, C.;
Synlett, 2000, 1557.
cat dihydroquinolinium tetlnphen ylhorate salts chiral lunine , 4 eq Oxone 8 ~ X JN~IZCO~,O"C , MeCN
68% (77% ee)
Page. P.C.B.; Rassias, G.A.; Barros, D.; Bethell, D.; Schilling, M.B. J. Chcm. Snc., Pcrkin Truns.1, 20011, 3325. chloropemxidase , t-BuOOH
Iiu,
sodium citrate buffer, It
s.;
Tetruliedron Lztt., 1999, 40, 1641.
flMe
Cr (salen) complex , MeCN
Ph
-10°C
Ryan, K.M.; Bouquet, C.;
83% ee
Ph Me Tetrahedron L.ett., 1999, 40, 36 13.
plyleucine urea-H2O2, DBU , THF Ph
150 min
Ph
Ph
Allen, J.V.; Drauz, K.41.;Flood, R.W.; Roherts, S.M.; Skidmore, J. Tetruherlron L.ztt., 1999, 40, 5417.
w
11202 , MeCN, 0°C
a t
Shu, L.;
*
EDTA , K2CO3
Ph
yq% o,\"'
*-
0 Tm-uherlrnn L*)tt., 1999, 40, 8721.
0
73% (58% ee)
A
Ph
84% (92% e e , RR)
Ph
Section 134
Ethers from Alkenes
10%N-anthrxenylmethyl substituted Cinchona alkaloid
11%
ph
WB.; Wainwright, P.G.
NaOCl , toluene , 2 d
355
*A ,,,\,"
ph
Ph
90% (81% ee)
Tctruherlron, 1999, 55, 6289.
78% (93% ee) Geller, T.; Roberts, S.M. J . Chent. Soc., Perkin Truns. 1, ZYYY, 1397.
NON-ASYMMETRIC COMPOUNDS
CTAB , VA-061, €120 10 q E P I I P , 80°C , 2 h
Me0
Me0
W Nambu, Y .€1.; ;Ratnesh, N.G.;
98% (55:45 trunsxis)
0
Anilkuinar, G.; Matsugi, M. Org. Lett., 2001, 3, 1157.
C F ~ C H ~ O,GO% H ~~0~ 5 % Na2III'O, , lxflux, 20h
*
67%
van Vliet, M.C.A.; hrends, I.W.C.E.; Sheldon. R . A . Synlett, 2001, 248.
Ti(1V) complex , T B I I P CI12C12,MS 4A ,it , 1 h
91%
35G
Compendium of Organic Synthetic Methods, Vol 11
Hz WOdf luoroapo ti te
t
G
Section 134
O
62%
kAhuJ,, Tetruhedron Lett., 2001, 42, 695.
80% (>99% after 21 h) Syrilett, 2001, 1305.
van Vliet, M.C.A.; Arends, I.W.C.E.;
PhSH ,PhH , 80°C, 1 d
A
Ph
-
+
Ph
SPh
Ph-sph
2% 97% + inontinoiilbnite K10 80% 6% Kanagasahapathy, S.; Sudalai, A.; Benicewicz, B.C. Tetrulierlron Lett., 2001, 42, 3791.
W s s e l . h;A n d w e , M.K.M. Tctruhedron Lett., 2001, 42, 2293.
Ph
knherlyst A-26(011-) , H202 dioxane , rt , 65 h
0
*
ph%rph
96% 0 Lakoura-i. M.M.: Movassaph. B.; Bahrami, K. Syntlz. Corirniun., 2001, 31, 1237.
S'
N II N
CD3CN, 25°C. 15 h
+
bS 45%
& a n . W.; Bargon, R.M. Eiir. J. Org. Chmi., 2001, 1959.
+w
aniphiphilic sugars, H20, , M o + ~ OH
ori
2"C, I d
Denis, C.; Misbahi, K.; Kerhl, A.; Fel-rikres, v.; Chenz. Cnrrmrtn., 20U1, 2460.
75% * ?
Section 134
357
Ethers from Alkencs
Fbse)2
cat F3C
Bu
cat NaOAc, 60% 1 1 2 0 2 , 1 h CIi3CH,OI1,2OoC ten Brink, G . 4 . ;Fernandes, B.C.M.; van Vliet, M.C.A.; Arends, I.W.C.E.; J. Chein. Sor., Perkin Truns. I, 2001, 224.
Bu"v
74%
Bu\ TiC$-NMe,, DCM -78°C
w
t-Bu
(90 SjGholm, IIeilunerling, hl.; Pradeille, N.;Somfni. P. J. Chcni. Soc., Perkin Ti-trris. 1, 2001, 891.
x.;
a
10)
quant
e:% I
80%
Pitts, M.K.; IIarrison, J.R.; Moody. C.J. J . Cherit. Soc., Perkin Truns. I , 2001, 955. 0.2.5 S x , cat Mo(O)(S,CNEt,),
acetone. 5 6 T , 15 h
Sinha, J.; Layek, S . ; Mandal, G.C.;
*
+.
+ 20% cyclooctene C h i . Conintun., 2001, 1916.
10 atin N 2 0 , PhCl , 140°C 5 % Ru-porphyrin c o m p k x
63%
Yamada, T.; Mashirnoto, K.; Kitaichi, Y.; Suzuki, K.; keno, T. Claem. Zxrt., 2001, 268.
358
Coinpendiuin of Organic Synthetic Methods, Vol 11
Section 134
CHCl, ,FeS04, Si02 ,31"C
Ghorbani, M. Mona?. Chcm., 2001, 132, 989.
;-
Legms, J.; Crousse. B,;Bourdon, J.; Bonnet-Delpon, D.; B6gu6, .I.-P. Tetruheilrnn Lett.. 200Z, 42, 4463.
.I
S8% (+ 45% acebphenone)
Iwahama, T.; Sakaguchi, S.; Jshii. Y, Hctcrocycles, 2000, 52, 697. Oxone , MeCN-aq EDTA, rt P
h
m
p
h
b
polymer-hound ketone
Afi
=a Ph
Sonp.; Liin, J.S.;Kim, S.C.; Lee, K.-J.; Chi, D.Y. Chein. Commun., 2000, 2415.
nA
Ph
2a 1 Illcpha , CHzC12, -78°C 5% CU(M&N)~PF~ ,8 h
Ph
77%
Andrus.;Poehlein, B.W. Totruhtdrnn Lett., 2000, 41, 1013. H202
94%
, NLIIICO~ , DZO ,25"C 70% conversion (99%)
Yao, H.; &&~dson. .. .
m
Ph
ph
I>&
J. Ani. Chew. Soc., 2000, 122, 3220.
4 ~ X J PhCIIO , B&t,NCl, It
ALfi
1.1 q chloramine M , 1 d * Ph Yanp,; Zhang, C.; Wang, X.-C. J. AJH.Chein. Soc., 2000, 122, 4039.
63%
Section 134
359
Ethers froin Alkenes
BIIOCII~CHO,-78°C BF3*OEt2,DCM
oms 7x76 (>20: 1)
Ph Micalizio, G.C.; Koush. W.R. Org. Lztt., 2000, 2 , 461.
A
30% aq H202, LiOH-Ii20, It ph ether, polymer-hound quaternary Ph iunmonilun salts ,20 h Anand, R.V.; Sinch. V.K. Synlett, 2000, 807. 1 % MeReO,, ~ 2.5
Bu*Bu
TFA
-
d ph
p
9
8
*
2.5 eq Na percarbonate, 6 h 12% pyr u o k J . Org. Chcni., 2000, 65, 4210.
w
c5111 1
O2 , tetrdin , PhEt , PhCN 60°C. 2 h
85%
*
10%~ N-hydroxyphthalimnide
0.1% C o ( 0 A c ) ~, 5% Mo(C0)6
Iwahama, T.; Hntta, G.; Sakaguchi, S.;
fi*
Ph
%
CdI1 I
79% (99:1 trunscic.) Chcni. Corrnnun., 2000, 163.
30% aq H 2 0 2 , acetone 0.1% Mn20(0Ac)2(TPTN) * FhhI'h Chcrii. Conniirm., 2000, 537.
Brinksma, .I.; IIage, R.; Kerschner, J.;
Owens, G.S.; Ahu-Oinar. M .M, Chenr. Conirnun., 2000, 1165. 0 1I
I
Me?C(CphTiCl, ,t-BuOOH ,28 h hexane ,6O"C
n
Ph'
OH I
X0% (44% erythro:rhreo) Sala, G.D.; Giortl:ino, L.; Lattnnzi, A,; Porto, A,; S c r e t u Tetrulterlrori, 2000, 56, 3567.
3 60
&f
Compendium of Organic Synthetic Methods, Vol 11
II 0
-
Section 134
Oxone, 0°C,30min acetone, NaIICO,
91% (2:3 a$)
Ferraz.,Muzzi, R.M.; de 0. Vicra, T.; Viertler, H. Tetruhchm LEtt., 2000, 41, 5021.
Ph
COzEt
1 0 . E :
, 10% Oxone
ph
KIISOs. NaIICOq, MeCN irq Na2EDTA ,-Z h ;Hayter, B,R.; Moss, W.O.; Reeves, J.R.; Wailer, J.S. Tetrahedron A . Y ~ I ~ I2000, I I I . , 11, 2M7.
8
60% 1 1 2 0 2 , c q c I r 2 o I I
quant
99%.
6 0 T , 20h Neimann, K.; Neumann, R. Org. Lett., 2000, 2, 2861. M%CIICH2CIIO1O2 DCM , Pd/Si02, r t , 6.5 h
98%
Gao, 11.; h c e l i c i . R ..I Syntli. . Cornnirin., 2000, 30, 1230. c o catidyst ,60°C
96%
M5CCI I( Me)CI I=C€12 Hunter, R.; Turner, P.;
e.
Syntli. Conzinun., 2000, 30, 4461
30%~ XIH202 ( 2 eq), 0.5% M c R Q
A
A0
* 97% 10% 3-fluoropyridine1 DCM Ph Molfsson. IL;Copbret, C.; Chiang, J.P.; Yudin, A.K. J. 01-8.Chern., 2000, 65, 8651.
Ph
w
Ph
Shu, L.;
11202 , CF,COMe, MeCN K2CO3
J. Org. Cliem., 2000, 65. XXO7.
93%
Section 134
Ethers froin Alkenes
36 1
modified S O , Sakamoto, T.; Pac. C. Tc.tru1iedronLett., 2000, 41, 10009.
2 eq Oxone ,pymlidine ,0.5 Py MLCN , 10 eq NaHC03 Adamo, M.F.A.; h a r w a l . V.K.; Sage, M.A. J. Am. Clieni. Sor., 2000, 122, 8317.
Ti(OCH2CI IzOh
H O-
hexane, 16 h
Massa, A.;
w
Ph
6%
-
OH 47%
Synlett, 2000, 1748.
0.1
BFi
-A
oo
Ph Oxone, 4 eq NaHCO, ,25”C * 81% aqMeCN, 16 h Minakata, S.; Takemiya, A.; Nakamura, K.; Ryu, I.; J(omatsu. M. Synlett, 2000, 1810.
Bu@, 60% H i 0 2 in CF3CII20II 2% I’~As(C:I-I~CI-I~C~H,,)~ ,reflux
-
95% van W e t , M.C.A.; Arends, I.W.C.E.; w o n .R.& Tetruhedron L z f t . , 1999, 40, 5239.
y. Ph
Oxone , aq MLCN Ph/Jh
Ph
30% Bn-N
)- N\ Bn
0
Carnell. A.J.; Johnstone, R.A.W.; Parsy, C.C.; Sanderson, W.R. Tetruhedron Ixtt., 1999, 40, 8029.
70%
-
362
Coinpendiurn of Organic Synthetic Methods, Vol 11
Section 134
MgioAh(OHhCO,, JXE
* C 5 30% aq H z q , i-PiCONH2 Na dedwyl sulfate ,70"C , 1 d Yamaguchi, K.; Ebitani, K.; Kaneda.K.. Org. Chern., 1999, 64, 2966. C5Hl1
H
l
l
w 0
80%
moist MMPP DCM,7h MMPP = inonopeiuxyphthalic acid Foti, C.J.; Fields, J.D.; &opp. P..I, Org. Lett., 1999, 1, 903.
w
Novozy1l1-435, HZO,
CSHI 1 ;-
0
.. .
=-
(MeO),C=O
C
5
H
I
67%
WarweI, S. Or#. Lett., 1999, I , 1025.
l 0
Do D
60% 11202, C ~ F I ~ B I . / P,70"C ~H Ct1Fi7
SeBu
L-
92%
5% C8F17
Betzemeier, B.; Lhermitte, F.; h o c h e l .
A
E Synlett, 1999, 489.
PhSII , II-Rho-zeolite , 5 h
Ph
*
hexane , 7 h Kurnar.; Pandey, R.K.; Iiegde, V.R. Synlett, 1999, I921 I-1202, DCM-EtOAc 5% perfluomheptadwan-9-one
van Vliet, M.C.A.; Arends, I.W.C.E.;
van Vliet, M.C.A.; k e n d s , I.W.C.E.;
~
Ph
SPh
0
Cherrt. Cnlnrnun., 1999, 263.
21 h
>Y9%
Chent. Conznzicn., 1999, 821.
69%
Section 135
Ethers from M i x .
I1
363
I12/C0 (400 psi) ,PhII [Rh(OAc)J,, 20 h 80%
OH Bergmann, D.J.; Campi, E.M.; u s o n . W.& ; Patti, A.F. Chem. Commun., lYY9, 1279.
&Ph
Ph ;-
Oxone, NaHCO, , H 2 0
*
MeClN , 10% chiral iminium salt
PhA
L
P
”
89% Ahned, G.; Garnett, I.; Goacoleu, K.; Wailes, J.S.Tetruherlron, 1999, 55, 2341.
amino acid-Schiff base Mn complex
\ - uB
0 2
,8O”C, 11.5 h
Wang, R.-M.; IIao, C . 4 . ; Wang, Y.-P. Syntli. Cornmun., 1999, 29, 1409.
SECTION 135:
65%
ETHERS, EPOXIDES AND THIOETHERS FROM MISCELLANEOUS COMPOUNDS
4’”’
1.5 “1 HGaCl, , BEt,
-&+Yo
THF ,0°C , 3-5 h
c,
c, 117 137 97% (84:16) Mikami, S.; Fujita, K.; Nakamura, T.; Yoiiiiiitsu, 11.; Shinokuho, H.; Matsuhara, S.; Qshima Org. Lrrtt., 2001, 3, 1853.
. ddv. . JS,; Subha Iteddy. B.V.; Srinivas, C.; Srihari, P. Syrtlett,
JhdsrLK; ,> de S 6, A.C.P.F.;Mcnczes, P.H.; Gonplves, S.M.C. Tetruhedi-on Lctt., 2001, 42, 4597.
20OZ, 854.
h P
364
Section 134
Coinpndium of Organic Synthetic Methods, Vol 11
A
Ph
PhCHO , Rhz(OAc), ,rt , 1 h CO2Me
* A ,l,llI\
Ph
hexatldCH2C12
76%
Davies. H .M.L.; De Meese, J. Tetruhedron Lett., 2001, 42, 6803.
1 . CpzTiH
TolSSTol
t
2. PhzI'X- ,TIIF-HMPA , 60°C Huane.;Wu, L.-L.; Xu, X.-11. Synrh. Carrzrtiun., 2001, 31, 1871.
0
HO II Ph VSVPh
OH
+
TolSPh
ph
02Me
78%
hP,Ph ,S, ,
MeCN , reflux, 4 h
98%
Miller, S.J.; Collier, T.R.; Wu. W. T e t r u l i ~ h mLett., ~ 2000, 41, 3781. 0
It PhNs\
2 eq TiC14, MeCN Ph
*
0°C. 15 inin
PhNs\
Ph
94%
. . Shlmlzu.; Shihuya, K.; Hayakawa, R. Synlett, 2000, 1437.
o(N:Et i
TMSXkPh , M a H
0
DCM
Abe.;Fujii, 11.; Yumasaki, A.; Kinome, Synrh. Coniniun., 2000, 30, 543.
76%
*
..
Y.; Takeuchi, Y.;
0 2
NaOH , TIIF, MLQII it,lh
'
-
Ph; Joo, Y.II.; Cho, 0
It
*
Ph) P h
+, ,#' '
86%
D.11.Syntk. Corrvriun., 2000, 30, 4489. WC16/Zn/THF, 10 inin
PhNs\ Ph J'irouzahadi. 1-1.; Karimi, B. S y n t h ~ s i s I, Y Y Y , 500.
t
PhSPh
96%
Section 135
365
Ethers froin M i x .
b Pb
P h 3 S n I I , AIBN , PhH 80°C
Crich. D.X.; IIuang, X.; JVewcomh. M. Or#. Lcjtt., I Y Y Y , I, 225.
95%
93% Genski,T.; Macdonald, (3.; Wei, X.; Lewis, N.; Tavlor. R.J.K. Synlett, ZYY9, 795. m S i M e 3
,BnOTMS
0.3 TMSOTf , MLCN, -20°C , 3 h
Suzuki, T.; Orivaiiia. T. Syntlz. Cornn,rm., Z999,29, 1263
L ,
Ph
57%
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 10
PREPARATION OF HALIDES AND SULFONATES
SECTION 136:
HALIDES AND SULFONATES FROM ALKYNES NO ADDITIONAL EXAMPLES
SECTION 137:
HALIDES AND SULFONATES FROM ACID DERIVATIVES 3 ecl Oxone, reflux, NaBr , 3 h
Ph-Co2H
iq MeCN , Na2C03 ,rt
-Br
t
88%
Ph
YOU,H.-W.; Lee, K.-J. Synlerf, 2001, 105.
NBS , MeCN , LiOAc
Br 42%
Jung, I.-H.; Lee, H. Tetruhedron Lett., 2001, 42, 1065.
p b m C 0 2 H
R a t ; Guin, C.: Maiti,
LiBr , aq MeCN , CAN ,it G. Tetruhedron k i t . , 2001, 42, 9253. NazMoO,, KBr , HzOz
Ph*m2rr Sinha, J.; Layek, S.; Mandal, G.C.;
t
1r20
* Ph*Br
mBr
Ph
Cheni. Coinniiin., 2001, 1916.
65%
Section 138
m
Ph
367
Halides froin Alcohols
C
0
2
1
NBS , LiOAc , M&N,
1
I-120
micmwaves , 1 min
&Br
-
Ph
84% ( 9 5 5 E:Z) Kuang, C.; Senboku, 11.; Tokuda. M, Synlett, 2000, 1439.
=
Ph
N-iodosuccinimide 10% B u ~ W - O ~ C C F ~
*
COZH
P
h
CH2C12, 15 min
-011
bmiC1= ionic liquid
It,
*
Id
a-
Ren.;Wu, J.X. Or$. Lett., 20U1,3, 3727.
r
+ succinimide
HALIDES AND SULFONATES FROM ALCOHOLS AND THIOIS hiniCl , MeS03H
PhcH,or
1
99%
Naskar, D.; Buy. S.I. Orx. Chern., 1999, 64, GX96.
SECTION 138:
=
BF,-OEt,, KI ,dioxllne /
98%
-
PhCI 121
it , 5 inin RU&l,.LBJLB.P.;Sadavarte, V.S.;LJppalla, L.S. Zetrdzedron L a , 2001, 42, 951.
.
NBS , PPh, ,CII,CI,
Ph 1t,5h Iranpoor. N.; Firouzilbadi. 11.; Aghapour, G. Synlett, 2001, 1176. Ph-s11
Br
95%
78%
ChCCCI3, diphos , rt
TIIF,3 h Pollastri. M.P.; Sagal, .IF.; Chang, G. Tetruhedrnn Lett., 2001, 42, 2459. P 2 0 5 , Bu,h%r,
toluene
100"C, 1 h Kato. Y.; Okada, S.; Tomimoto, K.; Mase, T. T'etruhedron Zxtt., 2001, 42, 4840
MeSO,II, N d , DCM
* PhCltI reflux, 15 min Kam.; Kamesh, G.; Laxinan, N. Synth. Corntnun., 2001, 31, 827. PhCI 1 2 0 € I
92%
Coinpendiuin of Organic Synthetic Methods, Vol 11
368
IF5 , Et,N-3 KF ,heptane
CIOHZ1 -OH
Section 139
C~oHz~-F
32%
80T,2 d Yoneda.: Fukuhara T. Clienz. Lett., 2001, 222. CeC13-7 H@ , NaI
T O I 1 MeCN , reflux Di Deo, M.; : Tonegiani, E.: . J. Orb. Cherii., 2000, 65, 2830.
I
-
48%~€IBr
HO( CHZ)xOI1
89%
; Bellucci, M.C.; Bosco, M.: Sambri, L.
85%
IIO(C€12)aBr cyc lohexane J.M.; IIeuft, M.A.: Rahhat, P. J. Org. Chenz., 2000, 65,5837.
w.
MqN=C(CI)SPh C I , DCM C,Hy-OH LC*IIy-C1 97% Gomez, L.: Gellibert, F.; Wacner. A.: Mioskowski. C. Tetruherlron Lxrt., 2000, 41,6049. TSCl, MqN(CIIz),NM%
C~II~~CII~~TS 94% MeCN , 10°C Yoshida, Y.; Shimonishi, K.; Sakakura, Y.; Koada, S.: Aso, N.: Synthesis, 1999, 1633. C7H pjCH20II
Me-N 5J
0 1 4
CJ
l a -
N Me t
NEt, , CHzCl2, It, 12 h Isohe, T.; Jshikawa. T. J. 01-8.Cliciii., I Y Y Y , 64,5832.
P hCH2OH Chaudhari, S.S.;
SECTION 139:
SOC12 , benzotriazole , rt
2'
93%
t
PhCHzCl
diy D C M , 10 inin Synlett, I Y Y Y , 1763.
95%
HALIDES AND SULFONATES FROM ALDEHYDES
BC13, hexane, reflux PhCIIO G.W,; Wu, Z. Tctrulicdron LL'tt., 2000, 41,579.
t
Ph-CHClz
90%
Section 143
369
Halides from Esters
cyclohex yl-BBr , hexa ne
P hCI-IO
PhCIIzBr
e
85%
1t,3h Kdbdlka.; . . Wu, Z.; Ju, Y. Tetruhedron Lett., 2000, 41, 5161.
P hCHO
BuBC12,Oz , hexme
* B u' 2h,rt Ph Kabalka. G.W; Wu, Z.; Ju, Y. Tetrahedron Lett., 2001, 42, 6239.
SECTION 140:
52%
HALIDES AND SULFONATES FROM ALKYLS, METHYLENES AND ARYLS
For the conversion R-I-I + R-Halogen, see Section 146 (IIalides from Hydrides). NO ADDITIONAL, EXAMPLES
SECTION 141: HALIDES AND SULFONATES FROM AhlIDES NO ADDITIONAL EXAMPLES
SECTION 142: HALIDES AND SULFONATES FROM AMINES NO ADDITIONAL EXAMPLES
SECTION 143: HALIDES AND SULFONATES FROM ESTERS (3
0.01% hexaliutylguanidinum chloride
115°C-
93%
12OoC,4h
Violleau, F.; Thi6haud. S.; Borredon, E.; I,e Gars, 1'. Synrh. Cornmun., 200Z, 31, 367. 70% IIFPy, NIS , DCM
<)(&Me
I h
Kanie, K.; Tanaka, Y.; Suzuki, K.; Kurohoshi, M.; Bull. Chetn. Soc. Jpn., 21100, 73, 471.
*
F
1
1
F
Y
7
0
%
Section 146
Cornpendiuin of Organic Synthetic Methods, Vol 11
370
SECTION 144:
HALIDES AND SULFONATES FROM ETHERS, EPOXIDES AND THIOETHERS
CeC13.7 HZO ,NaI , m N 0 2 pmpancxlithiol ,30inin
86%
Synlett, 2001, 1x97.
SECTION 145:
H3C'
(CHz)64Br
HALIDES AND SULFONATES FROM HALIDES AND SULFONATES M%SiFzPh
mu,
MeCN
reflux, 1 d Kvl?.lrla, J.; Mysik, P.; Paleta, 0. Synlett, 2001, 547. 1. B uLi , THF ,-78°C
2' '
4
0
H3C
72%
Y H 2 ) 6 d F
* M ,901nin
e
O
\ /
m w v e n . DS,;Nunn, M.I.T.; Fenwick, D.R. Tc.trultedron Ljtt., 2001, 42, 7501.
e 68%
P-Tol-IF,, NEt,-TIiF, DCM
* M e ( a 2) 13-F fluoroiwin reaction vessel, rt Sawaguchi, M.; Bara. ,&; Nakmura, Y.; Ayuha, S.; Fukuhara, T.; Yoneda, N. Tetruhedron, 2001, 57, 3315. Me(CHd13-1
e- ,Et,N-11 HF , DCM Me(cIJ2)lJ-I Me(CH2)IT-f; Sawaguchi, M.; Ayuba, S.; Nakanura, Y.;Fukuhara, T.; & S.: Y s Synlett, 2000, 999.
SECTION 146:
72%
8Wo
HALIDES AND SULFONATES FROM HYDRIDES
a-Halogenations of aldehydes, ketones and acids are found in Sections 338 (IIalide-Aldehyde), 369 (Halide-Ketone), 359 (Halide-Esters) and 3 19 (HalideAcids).
Section 146
37 1
Halides from I-Iy&ides
Br
In ,EtOH , aq NI14CI
95% (955 E:Z)
16 h
Ph
Ph
Panu. B.C.; Samanta, S.; Guchhait, S.K. J. Org. Cheni.,2001, 66, 4102. B nNEt,+ I QZDCM/MeOIi Kesynkin, D.V.; Tour. J.M. Or#. Lett., 2001, 3 , 991. CBr, / C€i2CI,
* %
Br 50% NaOH, 25°C 1 d , 10%Bu,NBr Pokin.; Lauenstein, 0.;Gunchenko, P.A.; Schreiner, P.R. J. Am. Chent. Sor., 2001, 123, 1842.
75% also prepaxd
iodide and chloride
u; Mason, 11.J.; Wu, X.; Endo, M.; Douglas, J.; Macor, J.E.
e m e
Tetruhcdron Lc,tt., 2001, 42, 3247.
C A N , MeCN, LiBr ,rt
*
OoM
Bov. S.C.; Guin, C.; Rana, K.K.; Maiti, G. Tetruhedron Lett., 2001, 42, 6941.
70% (3:7 0.p)
N B S , M e C N , r t , 17 h
93%
*
NII2 Br0 N H 2 Caiiibano, V.; Rodriguez, J.F.; Santos, M.; S a n z - T m; Ciu~efio,M.C.; Gonzilez, G . ; Syntlic)sis, 2001, 2175. Oxone, KBr , €120
\ /
McCN ,rt * B i O O M Tamhankar, B.V.; I)esai. IJ.V.;Mane, R.B.; Wadgaonkar, P.P.; Bedekar, A.V. Synth. Contniun., 2001, 31, 2021.
e
89%
372
Compendium of Organic Synthetic Methods, Vol 11
+
-
Section 146
Poc13 ,NEt3, DCM 40°C. 1 h
Jung, J.-C.; Jung, Y.-J.; Park. 0.-5, Synth. Coiiiinun., 2001, 31, 2507
NaI04 ,12, cat HzSO4
H
H
Bonesi, S.M.;
1. LiI-IMDS , THF 2. lluorinated Cinchona alkaloid 0
LzEt -78°C
0
5
Ph
75%
J. Heterocyclic Chein., 2001, 38, 77.
-
4
0
Ph
0
COzEt
8-
86%(76%ee) Mohar, B.; Baudoux, J.; Plaquevent, J.-C.; w d . D, Angcw. Chcin. Int. Ed., 2001, 40, 4214.
1. NCI ,W% HZSO4, rt, 20°C: 2. ice water
-
79%
I Chaikovskii, V.K.; Shorokhodov, V.I.; Filimonov, V.D. Russ. J. Org. Chcm., 2001, 37, 1503.
. .
shiaci. M.; Asghari, J. Bull. Cli~ni.Soc. Jpn., 2001, 74,1141.
Br
Section 146
Halides froin I Iydrides
ICI ,ZnO ,DCM ,rt
CpZFeB [3.5(CF3)&3 H,-14
55%
313
-@
8h 68% 41/53 (o/p) ukaiy.m a. . T.; Kitngawa, I-I.; Matsuo, J.-i. Tetruhedron Lett., 2000, 41, 9383.
KBr , NaB03* 4 IIzO AcOII ,rt ,145 h
Roche, D.;
; Repic, 0.;Blacklock,
Br
T.J. Tetrulierlr-on Lett., 2000, 41, 2083.
t-BuOBr , HNaX-zolite B r ether, a'l.,, 2 5 T , 1 h Sr;uith. K.; El-IIiti, G.A.; Ilaiimond, M.E.W.; Bahzad, D.; Li, Z.; Siquet, C. J. Chem. Sor., Perkin Truns. 1. 2000, 2745.
a
\ /
49%
NBS , acetone, cat €IC:l
* E i r O O 1 inin AukxsLR; Murphy, D.L.; Olson, R.J. Syntlz. Conuitun., 2000, 30, 2091.
\ /
IIZSM-5, A L O ~ I2, h
I'h-M Luliriski, P.;
' 12
e
* Br-c>-OMe
\ /
KI3r ,30%1rzoz, It
Narender, N.; Srinivasu, P.;
M
98%
I ; Raghavan, K.V. Syntlz. Comniun., 2000, 30, 3669.
, NdO, , HZSO,
t
AcOH , A q O Bicll. Clwni. Snc. Jpn., 2000, 73, 951.
Ph-r
65%
NC
Zdnkd.; , . Kuhota,
98%
A. Synlett, ZYYY, 1984.
96%
374
Compendium of Organic Synthetic Methods, Vol 11
.o
NaOH,CHI3,1d , r t
Schremer. P .&, Lauenstein, 0.;Butova, E.D.; Angew. Chcni. Int. Ed., Z999, 38, 2786.
t
. .
(PhM%Si),Cu(CN)Liz
TIJF, -78°C
4
rt
Section 148
v'
*
92%
SiMezPh
*
75%
ns, M.; u d f o r d . G .; Skinner, C.J.; Atherton, M.J.; Moilliet, J.S. J. Chern. SOC.,Perkin Trans. 1, 1999, 803.
t-BuOOI-I, HBr , HzOz
Barhate, N.B.; Gnjare, A S ..; -
A.V, Tetruherlon, 1999, 55, 11 127.
QBr
NBS , AcOH, 8 min
91%
Bu Hoffinann, K.J.; PhII Luliliski, P.;
I Synth. Connnim, Z999, 29, 1607.
HzSOj, MnOz, Iz
+
AcO1-l , AQO , 10°C BuII. C h m . SOC. Jpn., Z999, 72, 115.
PhI
Bu
63%
Toea.; Abe, S.; Nognmi, G.; Yokoyama, M. Bull. Chent. SOC. Jpn., Z999, 72, 2351.
SECTION 147:
HALIDES AND SULFONATES FROM KETONES NO ADDITIONAL EXAMPLES
SECTION 148: HALIDES AND SULFONATES FROM NITRILES NO ADDITIONAL EXAMPLES
Section 149
375
Halides from Alkenes
SECTION 149:
HALIDES AND SULFONATES FROM ALKENES
For halocyclopropanutions, see Section 74E (Alkyls from Alkenes). 0
Mg(ClOdh, BEt3/0, chiral his-oxazoline catalyst
%,,,
t
CO,Et
toluene, -78C, 5 h
A
%67%
(94% ee)
Yane.;Gu, S.; Yan, Y.-L.; Zhu, N.-Y.; Cheung, K.-K. J. Am. Clzenz. Snc., 2001, 123, 8612.
-
chiral R u catalyst, CCl, \P +h
Slmdl.;Wlodarczak, L.;
i Bu
rt, I d
Ph
90%
; Noels, A.F. Eur. J. Org. Chemi.t 2001, 2689.
Me ,N C
d I 4- C1
C1
Ar
*
h v , MeCN Ar = 4-dimethyl~inopheiiyl
131.1 35%
18%
Mella, M.; Coppo, P.; Guizzardo, B.; Fagnoni, M.; Freccem, M.; Alhini. A. J. Org'. Cficvii., 2001, 66, 6344.
4
1. S% Cp2ZrClz , ~ I I 1 7 0 T s 'IIIF, 55°C
@M@r
*
2. NBS , 0°C
de Annas, 1.;Hoveyda. A.H. 01.8. In.tt., 2001, 3, 2007.
/--/
Phc 73%
Ph
c5r11 1
Bu
zirconium dihydrate magent t
TIIF, r t , 4 h
Wipf. P.; Wang, X. Tetrahedron fxtt.,21100, 41, 8237.
x:I Br
C511,1
CS%I
82%
Section 150
Compeiidium of Organic Synthetic Methods, Vol 11
376
NaN3, NaI ,CAN, Me011 0°C , 3 0 inh
70%
Nair. V,;George, T.G.; Slieeha, V.; Augustine, A,; Balagopal, I..; Nair, L.G. Syrilett, 2000, 1597.
quant
Tallnrico, J.A.; Maltlick, L.M.; Snanner. M.1,. .I. C?rg. Client., 199Y, 64,344.
-
Mg 30% silica-supported Cu catalyst DCE, reflux, 18 h 0
0
I
I
Ts
TS
94%
Clark.,Filik, R.Y.; IIadclletoon, D.M.; Radiguc, A.; Sanders, C.J.; Thomas, G.U.; Smith, M.E. J. Org. Climi., 1999,64,8954.
SECTION 150:
3 +
HALIDES AND SULFONATES FROM MISCELLANEOUS COMPOUNDS
N, BF,
Br
N%PdCI,, 75% MeOlI, 40°C
B -*,:p,
0
Willis, D.M.; ,Ctronrin. R.M. Tctmhedr-nn Lett., 2000, 41, 6271.
Br
56%
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 11 PREPARATION OF HYDRIDES This chapter lists hydrogenolysis and related reactions by which functional groups are replaced by hydrogen: e.g. RCIi2X -+ RCII2-I1 or R-H.
SECTION 151: HYDRIDES FROM ALKYNES NO ADDI'IlONAI, EXAMPLES
-
SECTION 152: HYDRIDES FROM ACID DERIVATIVES This section lists examples of decarhoxylations (RCO2II
m i a ~ ~ w a v e15 s , min
*
-
R-H) and related reactions.
CO,H 98%
Ph
COZH 190°C Zara, C.L.; Jin, T.; Giguere. R.J. Synth. Coriiririrn., 2000, 30, 2099.
-
SECTION 153: HYDRIDES FROM ALCOHOLS AND THIOLS This section lists examples of the hydrogenolysis of alcohols and phenols (ROH
InC:I, , 2 a 1 Ph,SiIICl, DCM rt,2h Ph Yasuda, M.; Onishi, Y.; IJeba, M.; Miyai, T.; Baha.
pll
Ph
I>h
* Ph
Ph
-
87%
4.J. Org. Cherii., 2001, 66,7741.
H3PO2, cat 1 2 , AcOII 60°C
Gordon, P.E.; Fiv. A.J. Tetruhadrori L.elt., 20111, 4 2 , 83 I .
-
Ph-Ph
'Iuant
R-11).
378
Compendium of Organic Synthetic Methods, Vol 11
Section 157
cat Co(0Ach
85%
C r u d u C.M.; Allen, D.; Mikeluk, M.D.; Sun, J. Chenr. Cornniun., 200Z, 1154. Also via: Section 160 (Halides and Sulfonates).
-
SECTION 154: HYDRIDES FROM ALDEHYDES For the conversion KCI-10
R-Me, etc., see Section 64 (Alkyls from Aldehydes).
NO ADDITIONAL EXAMPLES
SECTION 155:
HYDRIDES FROM ALKYLS, METHYLENES AND ARYLS
H~(OAC)~,TBM ~
.to+
1:l THFMeOH Poliskie, G.M.;
SiM%Ph 48% M.M .; van Well, R. Tetrahedron Lett., 1999, 40, 589.
SECTION 156: HYDRIDES FROM AMIDES NO ADDITIONAL EXAMPLES
SECTION 157: HYDRIDES FROM AMINES
a
This .section lists exuiiples of the conversion RNH2 (or R2NH) + R-H. 1. MeSO2C1, Py 2. NaH ,NH2Cl
Wang, Y.; Guziec Jr.. F.S. J. Org. Chciii., 2001, 66, 8293.
96~87%
Section 158
Ilydrides froin Esters
379
NI-I NaNO2, AcOH ,EtOH
6
80%
i q Na hisulfite ,It, 20 h
1
Geoffroy, O.J.; Morinelli, T.A.; Meier. G.B. Tetrulzedron Lett., 200Z, 42, 5367. 2 q L i , ’ P I F , l d,rt P
h
\ O/
* P
e N Mez
h
O
a
\ / yuant
Azzena, U.; Dessanti, F.; M m i . G.; Pisano, L. Z’etruhedron
Zm.,1999, 40, 8291.
SECTION 158: HYDRIDES FROM ESTERS This section lists exainpIes of the reactions RC02R‘ -t R-H and RC02R’ + R’H.
-JOT HcO2N H2 at b 3 (CO) I2
N
Ph
dioxane , 160°C 20h
/
* P h
n 76%
Chatani, N.; Tatarnidani, EL; Ie, Y.; Kakiuchi, F.; J. Ant. Chpni. Soc., 2001, 123, 4849.
Ph2SiH2,(t-BuO),
*
68%
140”C, 20 h ; Kim. J.; Cho, D.H.; Chung, C.-M. Tetruhedron Z.m,
b
COZEt
Yu, Y.;ZhngJ.
1 . 10%CpzTiClz, TIIF i-PrMgBr ,rt , 4 h 2. 2N FIC1
Synrh. Coiirrrirm., 1999,29, 243.
#
9
2001, 42, 1073.
71%
380
Section 160
Coinpendiuin of Organic Synthetic Methods, Vol 11
HYDRIDES FROM ETHERS, EPOXIDES AND THIOETHERS
SECTION 159:
This section lists exainples of the reaction R-0-R'
5 eq Sin12,t-BuOH , 1 d
OB u Nakata, D.; Kusaka, C.; Tani, S.; OSiMe,
-
R-H.
*
PhH-HMP A
.
.
Tetruhcrlrnn Lett., 2001, 42, 415.
1 . "Cp2Zr" 2. D,O
*
80%
"Cp2Zr" = (Cp2ZICl2/2eq BuLi/THF, -78°C) Ganchegui, B.; Bertus, P.; Szvinoniak. J. Synlett, 2001, 123.
SECTION 160:
HYDRIDES FROM HALIDES AND SULFONATES
This section lists the reductions of halides and sulfonates, R-X
-
R-H.
cat Pd(OAc).L, 2 0 sec iniavw aves
>95%
Iones., Lockley, W.J.S.; Lu, S.-Y.;Thompson, S.P. Tetruhedron LEtt., 200Z, 42, 331. AcOH , HBr , aniline Br
Br
NH2
reflux, 4 h
Choi, H.; Chi. D.Y,J. Am. Cheni .Soc., 2001, 123, 9202.
70% NH,
Hydiides f m n IIalides
Section 160
38 1
Ni/C , Pph3 , K&03 M%NII=BII, ,7.5 h b s h u t z . B . L ; Tomioka, T.; Sato, K. Synlett, 2001, 970. InCI3 ,Bu3SnH , TIIP
PhCI1,Br
PhCII3 ,2h Inoue, K.; Sawada, A,; Shihata, I.; Baha. Tetruheclron Lett., 2001, 42, 4661. It
86%
1. BuLi, THF, -78°C 2. 9-(2H]-9-Ph-tluorene
-7X"CA rt
89%
mtrat.J.-C.; Pillon, F.; Rousseau, B. Tetruhedrnn h t t . , 2001, 42, 5001.
3% NiCIl(PPh3)2, 3% PPh3, 18 h M~NI-I*BH,,K2C03, M t C N , 40°C quant
Toinioka, T.; Pfeiffer, S.S. Tctrult~dronLett., 2001, 42, 7737.
;-
decaborane , 10%PdK:
*
A
94%
M t O I I , rt ,5 h Ph Ph Lee, S.H.; Jung, Y.J.; Cho, Y.J.; Yoon, C.-O.M.; Hwang, H.4.; yoon. Synth. Coiiriiiun., 2001, 31, 2251.
-
(2-f~171)3GeH,BEt3 ,TIIF, 1 h C12%-I Nakamura, T.; Yorimitsu, H.;Shinokubo, €1.; Oshirna. K. Brill. Cheiit. Soc. .Jpn., 2001, 74,747.
Ph
Br
Ni(R) ,TIIF, reflux , 12 h
t-
*
c121'25-H
4
Ph
w; Alvarez-Manzaneda, E.J.; Chahhoun, R.; Meneses, R.; Romera, J.L. Synlett, 2 0 0 1 , 485.
99%
89%
382
Section 160
Compendiuin of Organic Synthetic Methods, Vol 11
0r.i --
-
N-Hg
&C02Bn
i-Pr
011
-
Lr
3
5-
i-Pr
&C4Bn
93%
I Wang, Y.-C.; Ynn. T.-H, Chcm.Coimiun., 2000, 545. I n , H 2 0 , 8O"C, 3 h
*
>99%
0.01M sodium ddecylsulfate Ph Park, L.; Keum, G.; Kang, S.B.; Kim, K.S.; Kirn..Y. J. Chem. Soc.. Yerliin Truns. I , 2000, 4462. cat [Ni(OA~)~/Al(acac>3] , NaH 1
CXH17
TIIF, reflux , 15 inin, t-BuOH
n quant
Massicot, F.; Schneider, R.; Fort. Y.; Illy-Chexrey, S.; Tillement, 0. Tetmhedron, 2000, 56, 4165. N -i- Pr
N 4Pr
S d l z , MeOH ,It , 5 h
93% Aelteman, W.; Eeckhaut, A.; De Kimpe, N. Synlctt, 2000, 1283. 4
(M~o),P(o)II, 16 h
*
*
Br
Ph Br 4.5 NEt, , DMF ,70°C Ahhas, S.; Haves. C.J.; Worden, S. Tetrulicdron Lett., 2000, 41, 3215.
0-snBu2cI Br
Enholm.; Schulte n,
DMA , AIBN ,80"C NaBII4, 6.5 h J.P. 0r.g. Lett., 1999, 1, 1275.
M
Ph
93%
(2-fiuyl)3GeH , BEt,
' C12H25-H THF,lh Nakamura, T.; Yorimitsu, H.; Shinokuho, €I.; Qshima. K. Synletr, 2999, 1415. c12H2s-I
92%
67%
Section 162
IIydrides from Ketones
\ /
383
3 q i-PrMgBr ,TIIF, rt
c1
10% (C5H5hTiC12,2 d
93%
Hara, R.; Sato, K.; Sun, W.-H.; Takahashi. T. Chena. Conznzun., 1999, 845. Bu,hDII,, ‘I’HF ,r t , 5 inin P hCH,Br * PtlCH3 Ndrabimhan.; , . Swarnalakshmi, S.; Balakumar, R.; Velmuthi, S. Synth. Conmiin., Z999, 29, 685.
PdA4CM-41 , EtOH, H,
*
90%
0
43%
: Rahman, A.; Bandyopadhyay, T.; Haritha, Y. Synth. Conimun., Z999, 29,691.
SECTION 161: HYDRIDES FROM HYDRIDES NO ADDITIONAL EXAMPLES
SECTION 162: HYDRIDES FROM KETONES This section lists examples of the reaction KzC-(C=O)R
w
C o ( n ) , MI(^), 100°C , 1 4 h
-
RzC-II(R).
0+A+ CC”” CO2H
41% 13% 46% Sawatari, N.; Yokota, T.; Sakaguchi, S.; Ishii. Y. J. Org. Chern., 2 U U Z , 66, 7889.
2.5
0
.
; Lokot,
NaBH3CN, THF 2N aq 1I+
I.P.; Lakhvich, F.A. Synlctt, 2 U U Z , 1391.
0
384
Section 162
Compendium of Organic Synthetic Methods, Vol 11
A
Ph
H3POZ ,cat I 2
AcOIf ,reflux
n
* Ph
qumt
0
Hicks, L.D.; Han, J.K.; Frv. A.J. Tetruherlron Lett., 2000, 41, 7817.
Pt , K-10 , 5 0 har Hz
*
170°C. 15 h Tomk.;London, G . ; Bartbk, M. Synlett, 2000, 631.
cat R~C12(PPh3)3,PhH
*
t-BuOOH , 20°C
& 87%
Murahashi. S . 4 . ; Komiya, N . ; Oda, Y.; Kuwahara, T.; Naota, T. J . Org. Cherii., 2000, 65, 9186.
KMnO4 , CuS04.5
H20
DCM ,ultrasound, 3 h
-
Mdiarovh, M.; Toma. S.; IIeiihanovL, A. Tetrultedrnn, 2000, 56, 8561. Me2SiClII, 5% InCb
*
DCM , 2 Y C , 2 h Syrrlett, Z999, 182.
Ph Ph Miyai, T.; Ueba, M.;
1. N2H, ,toluene ,micmwavas 16 miI1 2. KOH , microwaves, 30 inin PhP h' Gadhwal, S.; Baruah. M.; ' I Synlett, 1999, 1573. ~
98%
Ph
Ph-Ph
70%
Ph
99%
95%
Section 165
3 85
Hy&-ides from Misc.
SECTION 163: HYDRIDES FROM NITRILES This section lists examples of the reaction, R-CEN .-+ R-H (includes reactions of isonitriles (R-NEC). NO ADDI'IIONAI, EXAMPLES
SECTION 164: HYDRIDES FROM ALKENES NO ADDITIONAL EXAMPLES
SECTION 165: HYDRIDES FROM MISCELLANEOUS COMPOUNDS
4-
Ph
S0,Ph
NI I Ph
Ph
Sin, AcOH, E O I I air ,rt , 1 h
0
Liu, Y.;
O r g . Prep, Procecd. Int., 2001, 33, 376.
L
2-
-yNHPh86% 0
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 12 PREPARATION OF KETONES
SECTION 166: KETONES FROM ALKYNES
q L Ph
Ph 15%50% Marchueta, I.; Verdaguer, X.; Moyano, A.; Pericbs. M.A.; Riera. A. Org. Lett., 2001, 3, 31.93.
SnC1, ,aq EtOH
Bosch.;Jefferies, L. Trtruheclron Lett., 2001, 42, 8141.
0
10% RuCp(MeCNXPF6, acetone 0 10% CSA, 1.3 € 1 2 0
02Me COZMe Trost. B.K;Brown, R.E.; Toste, F.D. J . Ant. Chenz. Soc., 2000, 122, 5877. MO2C
75%
Section 167
Ph
Ketones from Acids
=
ji
cat Tf2NI-I, H 2 0 ,dioxme
=
lOO"C, 2 d
Tsuchimoto, T.; Joya, T.;
Ph
387
Ph
; Kawakami, Y. Synlett, 2000, 1777.
1 . PhNHz , 1% CpzTiMe, 100°C , toluene
Ph
97%
2. S O , , D(3M
*
\
Haak, E.; Bytschkov, I.; Doye. S . A n p w . Cheiii. Int. Ed., 1999,38, 3389.
92% Ph
SECTION 167: KETONES FROM ACID DERIVATIVES 1. CDMT, NMM , THF, rt
2. EtMgX ,& I , 0°C
Ph
De Luca, L.;
'
Ph
Et
98%
-triazine CDMT= 2chloii~-4,6-d~iiethoxy-[1,3~] ; Pvrcheddu. A. 01%. Lett., 2001, 3, 1S1Y. graphite , 450°C , 7 6 0 m m
miauwaves (2x2 min)x6,450"C 90% E.J.; Chahboun, R.; Meneses, R.; Romera, J.L.
Barrero...; Alvarez-Manzaneda.
Synlett, 2001, 485.
MeMgBr , TIIF, 50°C
80%
r:
F
4%) when F is replaced with H
Zhane.; Terefenko, E.A.; Slavin, J. Tetruheclron Lett., 2001, 42, 2097. Nal3Ph4 , KF , acetone cat Pd(Pl'h,)2C1,, 9 inin * mic 1uwa ves
W ' 0 dn-.;Wci, B.; Iiu, Y.; Liu, Z.;Yang, Y . Sywrh.
BQ(-
Coiriiriiin.,
98% 2001, 31, 3885.
388
Coinpendiuin of Organic Synthetic Methods, Vol 11
Section 167
0
Inoue, K.; Shimizu, Y.; Shihata, I.; Baha.
99%
Synletl, 2001, 1659.
Ao1*
PhB(OI1)z , 3 % Pd(FG-aci), ,60"C
*
9% PCy3.2 NazCO3, 20 h disucciioyl anhydride Ghosh, K. Chrrrr. Corrirririn., 2001, 2084.
Ph
Qs&nLL;
U
Ph cathodJMtCN 65 % Sn cathoddMKN 0% Ueda, N. Bull. Chern. Snc. Jpn., 2001, 74, 755.
24% 78%
u;
1. Pd(PPh3)4 2. KOAc
.
90%
Ph hP'
lBu
*
74% Ph i Malladi, R.K.; Tejedor, D.; Kelley, S. Tetrultedrnn hrt., 2000, 41, 999. 3. B B u ~
Ph
)(
mesoporous silica FSM-16
= hv , hexane, i t , 12 h Ph Ph . Itoh, A.; Kodama, T.; Inagaki, S.; Org. LEtt., 2000, 2, 331. BzCI , Cat PdClz(dppf)
78%
*
78%
AgzO, KzCO,, 80°C Chen, 11.; Dene. M . - L Org. k t r . , 2UO0, 2, 1649. PhB(0II)z ,CSZCO~, tolut~e C1
I'h
S% Pd(PPh3)4, 100°C
Ah
Ph
.c
Jladdach. M.; McCarthy, J.R. Tetruhedrnn h t t . , I Y Y Y , 40, 3109
80%
Ketones from Alcohols
Section 168
389
80%
N.A,; Korolev, D.N. Tetruheron Lett., I Y Y Y , 40, 3057. M%SiSnBUg, 10% P(OEt), 110°C, 20 Inill C1 Geng, F.;
Bu '
'-.
S% [$(C3H5) PCICl]z
*
63%
Me 3 Si Tetruherlmn Ixtt., l Y Y Y , 40, 31 13.
Bu
PhOMe , 10 inin, reflux COZ 1-1
;-
,
,.
Enviiric at -EPIC
* M
L
C
.
)
\ /
Sadvaife, V.S. Synth. Coiirniun., l Y Y Y , 2Y, 2587.
SECTION 168: KETONES FROM ALCOHOLS AND THIOLS
1. (COXl)Z, DCM , DMSO -78"C, 90 Inill 2. NEt, ,-7X°C,2 h
ic,
3. "1 TIIF , --78"C + it
I ro
0
Fang.;Bandaruge, U.K.; Wang, T.; Schroeder, J.D.; Garvey, D.S. J . Org. Cheni., 2001, 66, 4019.
~ 69%
;
.
Section 168
Compendium of Organic Synthetic Methods, Vol 11
390
R~Cl2(PPh3)3,TEMPO, 0
2
1
*
98%
C6H13 100°C. PhCl ,7h C6Hl3 Dijksman, A.; Muino-Gonzilez, A.; Payerar, A.M.; Arends, I.W.C.E.; Sheldon. R.4. . I . Am. Chetn. Soc., 2001, 123, 6826.
x
(J
K 2 [ O ~ 2 ( O W 4 107 2 , 1 2 h
95%
t
arj t -B uOH
Ph Ph Diibler, C.; Mehltretter, G.M.; Sundenneier, U.; Eckert, M.; Militzer, 11.-C.;3eller. Tetruhcdron Lxtt., 2001, 42, 8447.
L .
S% V O ( X ~ K )MeCN ~,
*
80"C, 3 h
Ph
h.z
k , 98%
Ph
Maeda,Y.; Makiuchi, N.; Matsumura, S.; Nishimura, T.; ITelnura.. Tetruhedron Lett., 2001, 42, 8877.
ph-Y
C5H1
- phT
5% Fe(C0)S , hv (Pyrex)
OH
pentane, 2 h Cherkaoui, 11.; Soufiaoui, M.; Gr&. R. Tetruhedron, 2001, 57, 2379.
KM n0,-A120
Bi(N03)3 , 5 min
*
55%
81%
Synth. Comrnun., 2001, 31, 2691.
silica gel supported Jones reagent
DCM M.11.; Wiggin, C.J. Synth.
SiMe,
0'
Montmoiillonite
1.
93%
2o
hexane ,4h Ph Ph SiMq Patrocinio, A.F.; Moran. P.J.S. Synth. Coriirirun., 2001, 31, 2457
Samajdar, S.; Becker, F.F.; IhukJ!&
0
Coiiiriiiin.,
*
/J(
93%
2001, 31, 3383.
- A
PhI, 2% Pd(0Ac)z ,NaI-ICO, 0 1I
Bu,NCl , H 2 0 . 20 h
Ph
Zhao, M.;& M. -7&;Hu, R.-II.; Song, C.-S. Synrli. Conzrmn., 2001, 31, 3665.
87%
Section 168
Ketones from Alcohols
391
'Z
csw I
qcsH
[RuCh( PPh3)3/B uLi]
quant
TI-IF, 20 min ON 0 Uma, R.; Davies, M.K.; CsMsy, C.; Gs& & EUI:J. Org. Cirerrt.,2001, 3141.
1
liu(tmp)(O)2, M3E , 120°C
* 92% 10 atm N,O Ph Ph IIashimoto, K.; Kitaichi, Y.; Tanaka, H.;Ikeno, T.; Yamada, T. Chern. k i t . , 2001, 922.
&
Ph
Ph
1 . Fe(N03X.') H 2 0 , 100"C, 15inin
-
2. acetone, H,O
0
Zhao, Y.-W.; Wan!.
Y.-I,. J. Clietii. Res. (S), 2001, 70.
+Cn
Ph
95%
0
1. 1.1 a 1 P4-t-Bu. 'iliF/hexane 0°C -+ rt , overnight
Ph
Ph
2. p ~ buffer 7
PhS'
P4-C-Bu = t -BuN=P [-N= P( NMelX], Mamdani, H.T.; I-Iartlev. R.C. T~truhedrnnLcjrt., 2000, 41, 747.
58%
PhIO ,PPNO Ph
CiflII) s a k n catalyst
Ph - ..
hdam.;Gelalcha, F.G.; Saha-Miiller, C.R.; Stegmann, V.R. J. Org. Ch~ni., 2000, 65, 1915.
JdOI1
PhI(OAc), , DCM, 20"C, 5 h
*
CiflII)-salen C1 Adam, W.; Jlaira. S.;IIerderich, M.; Saha-Mijlles, C.R. Org. Lett., 2000, 2 , 2773.
10% N-hydsoxyphthalinkle , EtOAc 0.5% Co(OAc), , 5 % mcpha
Glr 13
70"C, 3 h
99%
90%
*
Iwahama, T.; Yoshino, Y.; Keitoku, T.; Sakaguchi, S.; Ishii, Y J. Org. Chern., 2000, G5, 6502.
Coinpendium of Organic Synthetic Methods, Vol 11
392
(,i
Al2O3,Br2-Alz03 ,DCM 1 ,
P
h
)$
*
Bi(NQhe 5 H 2 0 , Ac0I-I
Ph
4% Cu(OAc)2, HzO
0
83%
Ph
Love.;Nguyen, B.T. Synth. Cotilnzun., 2000, 30, 963.
Phh
Section 168
Ph 99%
0
Tymonko, S.A.; Nattier, B.A.; Mohan. R.S. Tetrulierlron Lett., ZYYY, 40, 7657.
,
-
B
U
Ph G 01.1
PhBr , 1% Pd2(dhah-CHCI3, 100°C 2% R-( +)-BINAP ,dioxane , KzC03
x
1% mcpha, 1% TEMPO
+
Jy
1% V0(OEt)Cl2, rt
Ph
0 2
, MeCN, 1.5 h
96%
92%
1% B u f l B r , CIIzClz,rt
C6II13 C6H13 pvchnovskv. S.D.; Vaidyanathan, R. J. Or#. Clwm., 1999, 64, 310
Ph
1
Ph
Nishimura, T.; IJernura. S,.I. AIJI.C h i . Snc., 1999, 121, 11010.
Ph
0
94%
0
K1TclhrlTd.; . , Ochiai, Y.;Takizawa, S.;Takahata, 14.; Neinoto. I
Chctit. Conirniin., I Y Y Y , 1387.
RuCI,(PPh3)3 , TEMPO 0 2
, 100°C , PhCl , 9 h
Dijksman, A; Arends, I.W.C.E.; &Idon.
/uu
Ph
Ph
t
C6H13
1
90%
Chern. Cornniun., 1999, 1591.
F~C13.6L I Z 0 , solid stale
90°C
Jy
* Ph
01.1 Zhou, Y.-M.; Ye, X.-R.; )
0
95%
Section 169
Ketones from Aldehydes
A
><x
393
,acetone,2s"C
*
98%
I'h Ph Baumstark, A.L.; Kovac, F.; Vasquez, P.C. Can. J. Chin., 1999, 77, 308. 11202, Na2WO.4, 90°C, 4 h
77%
Me(C,NI7),N IISO, C3I-I7 Sato, K.; Aoki, M.; Takagi, J.; Zirnmerman, K.; pJovori. Bull. Cheni. Sor. Jpn., 1999, 72, 2287.
REVIEWS: "Selective Oxidation of Secondary Alcohols,"
Tctr-uhc.h-on, 2001, 57, 9765.
Related hlethods: Section 48 (Aldehydes from Alcohols and Phenols).
nph
SECTION 169: KETONES FROM ALDEHYDES
Phh
C
I
I
O
1. PhLi, TIIF 2. TMSCl
*
98%
Ph
Nudtlmdn.; , . Garcia, G.V. .J. Org. CIicrn., 2001, 66, 13x7. PhCI-10, BF3*OEt2 , CHzCl2
Ph It, I d Ph Chan, P.W.11.; Kamijo, S.; m a l n o t o . Y ,Synlett, 2001, 910.
P hC1I 0
C I I ~ X I I B US% , Rh(PPh3),CI
LBu
75%
20% 2-amnino-3-picoline , micmwaves ph 10 min Jun. C.-IL; Chung, J.-H.; Lee, D.-Y.; Loupv. &; Chatti, S . Tcri-uhedron Lett., 200Z, 42, 4803.
B uC1 I 0
, toluene , 80°C , cat (BzOk cat N-hydir,xyphthalirnide
4Lv BU
67% Tsujimoto, S.; Iwahama, T.; Sakaguchi, S.; Lshii. Y . Clierrt. Cornriiun., 2001, 2352.
Compendium of Organic Synthetic Methods, Vol 11
394
6
Section 170
C3H7CII0, SLCO~, PhH 5% t-B uOII , 2 d
C3H7 81%
0 OH 0 Pacut, R.; Griinm, M.L.; Kraus, G.A.; Tanko. J.M. Tetruhedron LL'tt., 2001, 42,1415. 1. 1IZNNI-ISO2Tl)l
P hCI-I0
2. PhCHO , EtOH , NaOEt 55°C , 2 d
Anele.;Neitzel, M.L. J. Org. Clzeni., 2000, 65,6458.
r";CTs
Ph
PhCHO
*
NLI+
aq THF, 50°C. 2 d
LB
42%
59%
8".
Ph wal. V.K.; de Vincente, J.; Pelotier, B.; IIolrnes, I.P.; Bonnert, R.V. Tetruhedron Lett., 2000, 41, 10327.
b
Xia, M.;
e
.
,
Ph2I' CI- , 5 % PdClz t
DMF ,2076 LiCl ,40"C, 3 h
Ho
89%
SyntA. Cnnrrrrun., 2000, 30,531.
c€10 Br
1. h-pr
, EtOH
5% Pd( O A C ) ~2, 2. 100"C, 1 d
KOAC 71x6896
. V,; Quan, L.G.; m o t o . Y , Tetrukedron Lxtt., 1999, 40,4089.
SECTION 170:
Pr
KETONES FROM ALKYLS, METHYLENES AND ARYLS
This section lists exainples of the reaction, R-CI-11-I<' + R(C=O)-R'.
395
Ketones from l n i n e s
Section 172
NO ADDITIONAL EXAMPLES
SECTION 171: KETONES FROM AMIDES
"bNzo , NaH , DMF
1 . NC
I Me
BrJ/NO , Me Selvamumgan, V . ;
*
yJ
Bu
'
2. BuMgBr , TfIF, 0°C 3 . CuSO, , aq MeOH ,reflux
0
Tetruhedron, 2001, 57,6065.
78~76%
57% (45% ee) ; P6rez-Encaho, A. Tetruhedron, 2000,
AndrCs, J.M.;
Et0,CH r-j
EtO,CII~ BuLi , TIIF
P
h
56, 1217.
q0
N
D
-78°C
*
Ph7fBu 0
80%
w e u n t a . S.;Mondal, S.; Das, D. Tetruliodron k t t . , ZYYY, 40,4107.
REVIEWS: "Base Catalysis in the Willgerodt-Kindler Reaction," Kenard, M.; Lanihert, D.; IsitM. Org. Prep. Prnrcerl. lnt., 2001, 33, 335.
SECTION 172: KETONES FROM AMINES
A
N-NMe2
C ~ t 1 3 * II2O-SiQ13 7 min
*
jl
Ph niicrow ave s Ph Yadav, J.S.;Suhha Reddy, B.V.; Reddy, M.S.K.; Sahitha, G. Synlett, 2001, 1134.
90%
Compeiidiuin of Organic Synthetic Methods, Vol 11
39B
Section 172
1.10% [(%H,,XRhCl]2 bluene, 150°C
c:x
92% (95% ee) c1 Jun. C.-It; Hong, J.-B.; Kim, Y.-I-1.;Chung, K.-Y. Angew. Clienz. Inf. E d , 2000, 3Y, 3440.
1 . 5 %RhCl(codyPPh3, NaOr-Bu xylem, 125"C, PN,26 h
N
2. H30+
H
*
PhP h'
Ph IIartunr. J . J . Am. Cliem. Snc., 2U00, 122, 12043. Me o/
J-( illllll~~l
/
CuCl2, 12 h
Et +3117 MC
-
Et
%
C3IT7
M~ 89%~(99% ee)
Enders.; IIundertmark, T.; I.azny, R. Syntl?. Con~niun.,1999, 2Y, 27.
86%
Section 173
397
Ketones from Esters
SECTION 173: KETONES FROM ESTERS PhSe
(1132=CIIC02Me, PhII
d-K
Bu?SnI-I, rcflux
Bennasar, M.-L.; Koca, T.; Griera, R . ; Bosch, .I. Org. Lett., 2001, 3, 1697. S
5 eq Mg , MeOII icflux , 30 min
CO2Me
OZN
$9: COzMe
*
O2N
Rho.;KO,B.-S. Synrlz. Coiwrun., 2001,
31, 283.
EIS
Lieheskind, L.S.;
0 1I
J. Ani. Chein. SOC., 2000, 122, 11260.
0 1I
81%
1. CFi(0i-Pr), , EtMgBr 2. MsCl , I’y
E0,C 014
Cho, S.Y.; Cha&.€L Org. Lett. 2000, 2, 1337.
OTBDPS
0
62~58%
Section 174
Compendium of Organic Synthetic Methods, Vol 11
398
esterase fioin Murckuntix polyirwrplio
U; .. Shimoda, K.; Kawano, T. Tetruhedron Asyntnz.
A3
Ph
PhB(0Hk , Pd catalyst 6 KzC03 , Nal
DMA ,9S"C
Br
Phh P'
88% (+ tebahydrothiophene) Org. L%., 2000, 2, 3229.
Savarin, C.;
5 OMe
'.
IIwang, J.P.;
2000, 11, 1063.
CF3S03II , PhH 8S"C, 8 h
'
Tetruherlron., 2000, 56, 7 199.
75%
1. B uMgBr , THF , 0°C
Lee, N.R.; Lee, K.I. Synth.
SECTION 174:
$opNB
I Mt!
2. PhLi , "HI', 0°C
Coriiiiiun.,
It
0
76%
I Y Y Y , 29, 1249.
&
KETONES FROM ETHERS, EPOXIDES AND THIOETHERS A'(K+jF5)3 DCM 9
1
-
0°C
* IIIIIIY
MLO
/
opm
96% M a J(ita. Y.; Furkawa, A.; Futamura, .I. IJcda, ; K.; Sawama, Y.; IIamamoto, €1.; Fujioka, H. J. Org. Clierii., 2001, 66, 8779.
Section 175
Ketones from Nalides
399
1 . PhBr , Pd(OAch, dppp , TlOAc , 8 0 T 2. PhBr, 5% Pd(OAc), , PPhn , 100°C
b '
NMe2
3. aq HCI, TBME
j
Nilsson, P.: Larhed, M.: fInlll~ere. 4J. Am. Clicm Soc., 2001, 123, 8217. OTMS
A w: ..
ph)JL 65 56
ph
NaBr03, NH4Cl, 80°C aq MeCN , 45 min
75%
Karirni, A.-K. Synth. Corninim, 2001, 31, 759.
I
Bi , cat Cu(OTf), , 0 2 DMSO, 100°C
*
74%
Antoniotti, S.: 1)uriach. E, Clieni. Cortnnun., 2001, 2566.
0 x O'IMS
~ s . - K Ryu, . ;
Ph,Sh(OAc)2,catPdCJ DME/MtCN , H 2 0 , rt , 6 h
68%
K-C.; IIong, Y.-T. .I Clzern. . SOC., Perkin Truns. 1, 2000, 3350. 70% t-BuOOII , cat CiO, z
Ph DCM , rt , 1 h Ph Chandrasekhar. S.;Mohanty, P.K.: Kamachander, T. Synlc*tt, l Y Y 9 , 1063.
-
77%
Singh, V.; Khuriina, A,; Chaudhary, S.: Singh, J. Synth. Cortrntun., I Y Y Y , 29, 3439.
;-
SECTION 175: Ph
C1
KETONES FROM HALIDES AND SULFONATES PhI, Fe(CO)S , DMI' , e-
ji,,
Bu4NT3F4,cat NiBr,(hpy) * ph 82% Dolhem, E.; Barhdadi, R.: Folest, J.C.: N6d61ec, J.Y.: Troupel, M. Tetruhedrun, 2001, 57, 525.
400
Section 175
Compendium of Organic Synthetic Methods, Vol 11
1 atm C O , SnMe,
3% Pd(OAc), ,dppp * a m o 83% NEt, ,DMF ,6O"C Garrido, F.; Raeppel, S.; &IM-,&. . Lautens, M. Tett-uliedron Lett., 2001, 42, 265.
\ /
F'hzMeS X C1
M
1. EtMgBr 2. CuCN.2 LiCl , -78°C
e Phz
3. air, aq NR4CI
C1
Inoue, A.; Kondo, J.; Shinokuho, H.;
-+
SiMePh,
0°C
75% 0 J. Am. Clzetn. Soc., 2001, 123, 11109.
cat PdClZ/PPh3 , 5 b i CO ~
* E PhB(OH)2 , KZCO, Ph 8 O C , 20 h Couve-Bonnaire, S . ; .J.-F,; Mortreux, A,; b t a n e t . Y , Tetruhedron Ldt., 2001, 4 2 , 3689.
\
/N
80%
mBr
1. cat Pd(dha)z, PPh3 ,rt toluene, 15 inin 2. toluene , 110°C +OEt
SnBU,
0s.
J.-Y,; Prinault, G.;
3.1MI-ICI,rt,ld J. -C. Tetruherlron, 2001, 57, 2507.
m.
A,,
,Sdz
PI1
qr
uPh
TIIF, r t , 1 h * Ph Ph Back, H.S.; Yoo. B.W. ; Keum, S.R.; yoon. C..M.; Kim, S.H.; Kim, J.11 Syntk. Cnntniun., 2 0 0 0 , 30, 31.
82%
pllcuI:MF (cI%2)4 a(cI)ck* o$+ 0°C , 10 h
(CH2)4 Ph'H2)4
d.
Y.; Narita, K.; -chi.
(29 T. Tetruherlron Lett., 20U0, 41, 109.
/
Ph
62) 91%
Section 176
Ketones fiwin Hydrides
401
PhH, AlCl3-nBPK, 65°C , 4 h
Aph
PhCYJ13 LPh nBPK = n-butylpyiidimium chloroaluininate ionic liquid Reheiro, G.L.; Synth. Corrtnritn., 2000, 30, 1605.
S0,Me
GO%
*?Yo
B u ~ S I I I IAIBN, , 100°C
NLBr
0.02M PhH , 80 atin CO
.
.
7 .
81% (+ 6% reduction)
;. .. Alvarez-Garcia, A,; Muchowski, J.M. Tetruliecfron IA'tt., 2000, 41, 3035.
Pd(PCy,), 2 q Cs pivalate
quant
-
DMF , 110°C Carnpo, M.A.; m c k . R.C.. Org. L d t . , 2000, 2, 3675.
CKII,7-I
& n
cotS%
CII2=C1ICO2Me1 CO ,AIBN ,80"C
*
(Me,SiXSiII, supercritical CO, , 5 h Kishimoto, Y.; Iknriva. T. J. Org. C/wiiz.,2000, 65, 7656. C711,sBr
1. Mn* 2.
1
CKH
+ C7%
90%
0
Bu
81%
Bu Gahiez. G.; Martin, A.; Dclacroix, T. Zetruherlron Lett., ZYYY, 40,6407.
Related Methods:
Section 177 (Ketones from Ketones). Section 55 (Aldehydes from IIalides).
SECTION 176: KETONES FROM HYDRIDES This section lists examples of the ~-eplaceinentof hydrogen hy ketonic groups, R-II + R(C=O)-K'. For the oxidation of inethylenes, KzCI-Iz -+ R2C=O, see section 170 (Ketones from Alkyls).
Compendium of Organic Synthetic Methods, Vol 11
402
Section 176
A c ~ O DCM , ,5% AgShFs 2.5%(PhCNhPtCIz
76%
Fiirsmer.~.; Voigtliinder, D.; Schrader, W.; Giehel, D.; Reetz, M.T.Org. Lett., 2001, 3, 417.
Ottoni.;de V.F. Nedcr, A,; Dias, A.K.B.; Cruz, R.P.A.;Aquino, L.B.
OOMC
Org. Lett., 2001, 3 , 1005.
Acl0 , 1% In(OTf),
* -0Me 99% LiC104, MeNOz SOT, 1 h Chapman, C.J.; Frost. C.G.; Hartley, J.P.; Whittle, A.J. Tetruhedron Ldt., 200Z, 42, 773.
AcZO , AlCl3
b
op
90% A l ~ l l a C.A.M.; , Aquino, L.B. Tetruherlron Lett., 2001, 42, 1467. 0
II
II
I
I
H~IO,~CIO~
I 61%
V
.
.
I
Tetruliedron k t t . . 2001. 42, 3355.
0
0
Section 176
403
Ketones from Hydiides
@ 0
hv (>495 nm) ,02,rt E- tetraphenylphoxphin
C€12C12,rt , 2.5 h
OH
*
82%
0
CusSv.;Belotti, D. Tetruheclron Lr.tt., 2001, 42, 4329. KMnO4/CuSO,-5 1120
~o
neat, 1.3h
Shaabani, A.; J-ee. D.G. Tetrd~erlronLett., 2001, 42, 5833
4
Ph
Ce(OTf), , MtCN ,r ~ t
/
- 1Ic: Ph
P I1
+ 15%
H20 9.5% 16.4%)1 1 2 0 99.7% L.d.rlll.; Herbert, M.; Cushnyr, B.; Bhatt, A.; Terrano, D. J. Chern. Soc.. Perkin Trans. 1, 2001, 578.
+
90%
2A.c5~4O (PhCNhPtC12 , DCM , 5 %AgShFs
85.7% -
%*
*
Furstner.;Voigtlinder, D.; Schrader, W.; Giehel, D.; Reetz, M.T. Org. Left., 2001, 3 , 417.
Taber.;Sethuraman, M.K. J . Org. Cl7c~in.,2000, 65, 254.
404
Compendiuni of Organic Synthetic Methods, Vol 11
R U , ( C O ~ ,cprz=crIz
C O , 2 0 a h , toluene 160°C. 20 h
Section 176
. ,
Ie, Y.; Chatani, N.; Ogo, 'I.; Marshall, D.R.; Fukuyama, T.; Kakiuchi, F.; J. Org. Chem., 2000, 65, 147.5.
BzCl, Ga(0Nfh
Ph
Nf = nonafluoiubutanesulfonate Matsuo, J.-i.; Odashima, K.;
0
Synlett, 2000, 403.
cis[ RuV'( 6,6'-Cl$py)~O~](C104)~ McCN ,it, Nz , 3 0 inin
Che. C . - N ; Cheng, K.-W.; Chan, M.C.W.; Lau, T.-C.; Mak, C.-K. J. Org. Chern., 21100, 65, 7006.
1. NaOCl , NaBr ,TBAH-HS04
LPh
* Ph
2. H20
Ph-Ph
86%
Clark, J.H.; Grigoropoulou, G.; Scott, K. Synth. Coninzun., 2000, 30, 3731.
M
e
\O /G
ACZO,Cat Sc(OTf), , 4 h MeN02,5O0C 89%
Kawada, A.; Mitainura, S.; Matsuo, J.-i.; Tsuchiya, T.; Bull. Cheleni. SOC.Jpn., 2000, 73, 2325. incpha ,N a H C Q ,air
CHzC12, rt
MitIz; Xia, C.; Tian, H. Tetrulicrlron Lett., I Y Y Y , 40, 8915.
88%
0
99%
-
Section 177
Ph
Shi, Q.-Z.;
Ph 1
405
Ketones froin Ketones
NaB1.4 , C L O ~ ,95"C, 1 d
aq dioxane Ph J.G.;Cai, K. Syntlt. Conunun., I Y Y Y , 29, 1177.
90%
1. Na , C3H7C02Me TIIF, 25°C
periasamv. M .; Keddy, M.R.; Bharathi, P. Synth. Corrinrun., ZYYY, 29, 677.
C103-Si02.140"C
t
Ph-Ph
a
5h Ph Bose. D.S,; Sunder, K.S. Synfh. Cornrnicn., J Y Y Y , 29, 4295.
CI-I~(CO2II)2, PPA, 2 h GO-80°C
-
92%
Renault, 0.;Dallemagne, I).; Pitult. S. Org. Prep. Proceed. Int., 1999, 31, 324.
SECTION 177: KETONES FROM KETONES
This section contains alkylations of ketones and protected ketones, ketone transpositions and annulations, ring expansions and ring openings and dimerizations. Conjugate reductions and Michael alkylations of enone are listed in Section 74 (Alkyls from Alkenes).
For the preparation of enatnines or iinines froin ketones, see Section 356 (Anline-Alkene). 1 . LDA , TIIF, -78°C , TI-IF 2.2.S%[Pd(1~3-C~IIs)CI12
7.5% his -f errwe ne- his-phosphine ligand , 3 h , allyl-0,COEt 90% (82% ee) You, S.-L.; JIou. X.-L.: Dai. I,.-X.; Zhu, X.-7,. Org. L , t t . , 2001, 3, 3149.
Section 177
Compendium of Organic Synthetic Methods, Vol 11
406
1. EtOK ,-78"C,2 5 h 2. cat BuLi , LiBr , HMPA -7XC , 12 h ,
pu
Yu, W.;
I
Tetrukedron Lett., 2001, 42, 369.
iMe
S -'3. _
Ph-02CCF3
cat I'd(
q3-GI 1s C H=CH CH2)(CF~COZ), * p&ph
'I'IIF, reflux
60%
Ohora, Y.; Ogawa, Y.; I~nni,Y.; Kawamura, T.; TSUJLX. J. Am. Clirrit. Soc., 2001, 123, 10489. OTMS
Ph
0
BF,.OEt,, CH2C12, -78°C ;-
85% (88:12 &ns:cis) Kimura, C.; Hosoya, 11.; Yunadoi, S.; Yokoe, I. Tetruhedron Lett., 2001, 42, 1095.
, 2 . 4BEt3
5% pd(OA~)z,10% PPh3 THF,rt,S h
Horino, Y.; Naito, M.; Kimura, M.; Tanakn, S.; W r u . Y, Tetruhedron Lett., 200Z, 42, 31 13.
;-
Bahu, S.A.; Gunnnathan, C. Synth. Corizmun., 2001, 31, 1205
A
NBu3 , dioxane ,5% RuCb-n IIzO
Ph 3 ~1 PPh3, 18O"C,40 h Cho. C.S.; Kim, B.T.; Lee, M.J.; Kim, T.-J.; Shim. S.C. Angew. Cheni. Int. Ed., 2001, 40, 9SX.
Ph
70%
Section 177
Ketones froin Ketones
407
1 . 0.1 chiral imide 2. 2,6-di-t-Bu-phenol
TIIF, -78°C Yanagisawa, A.; Watanahe, T.; Kikuchi,
>99% (90% ee)
T.;mote. U,J. Org.
Chem., 2000, 65, 2979.
1. T f 2 0 , 0"C, DCM
2
i- Pr
)(/
Ph
-
3. t-BuOK, DMSO
N
O
F 96~91%
v. A.R-; Zhang, S.; K u r ~1.; , Wang, M. Org. k t t . , 2001, 3, 2807.
6
P(t-Bu)3
ecl
, 1"/u I'd( OAc h
, 1.3 NaOt-Bu,
PI1
Fox, J.M.; IIuang, X.; Chieffi, A,;
\ 91% J. Am. Cliern. SOC.,2000, 122, 1360.
toluene, 8 0 T ,12 h *
"If c8
C,III7Br, 4N NaOI-I , 100°C calix(n)arene catalyst , 1 0 h
0
.. . Shlmlzu.; Suzuki, T.; Sasaki,
6
Ph
Y.; Nirai, C. Synlett, 2000, 1664.
2. 1. LDA 2 5 % Pd2(dba)3CIIC1,
ACO
*
Ph&+
17
Phh
86%
0
1111111111
0
(87
Braun. M.; Lnicher, F.; Meier, T.Angew. Client. Int. Ed., 2000, 39, 3494.
13)
Compendium of Organic Synthetic Methods, Vol 11
408
1
Section 177
A
1% Cu(xac), , 2.5 eqBujSnH
*
85%
PhH, reflux , 5 h C I-INz Ph Ph Tan, Z.; Qu, Z.; Chen, B.; Wanc. L Tetruhedron, 2000, 56, 7457.
&
C N ~ X H C ~ HAcOII, I ~ , 0, cat Mn(OAc)z, 80°C
C6H13
cat Co(0Ac)z
Ph Kawatsura, M.;
+.
Chenz. Conutzun., 2000, 2317.
Iwahama, T.; Sakaguchi, S.;
ji
85%
2% Pd(dba)2/ferrocenylphosphine ligand PhBr , NaOt-Bu, TEIF
*
2 5 T , rt
J. Am. Cl7crn. Snc., 1999, 121, 1473.
Ph
5 % child ligand , 2 eq LDA 2.5% [(q3 c3 I11,)PdCl],
MqSnCI ,30inin, DME -0AC
Trost.;Schrocder, G.M. .I. Am.
99% (86% ee) Clieiiz. SOL-., ZYY9, 121, 6759.
Amauld, T.; Barton, D.H.R.; Norinant, J.-F.; Doris.
. J, Synth.
Cnttzntun., 1999, 2Y, 117.
BJ. Org. Clwn., 1999, 64, 6915.
99%
Section 179
Ketones from Alkenes
409
Vdrmd.; . , Kumar, D. Synrh. Conunun., 1999, 29, 1333. Related Methods: Section 49 (Aldehydes from Aldehydes).
SECTION 178: KETONES FROM NITRILES
, cat sinIz
PhCN
t
cat NiI, , 30 inin, rt 11.-Y.; Song, S.-E. Totruhedron Lttt., 2000, 4 1 , 937. 1.
x/,
68%
Ph
mBr , 4 q Z n , 0.4 AICI, ?HI;, 2 h
2 . 2 M IICl
61%
U ,, S . - Y . ; Lin, L . 4 . Tctrulic*dr~in LLTtt., 2000, 41, 8803.
B
SECTION 179: KETONES FROM ALKENES
0, , McSO,II , act MLK"
10f%I'd(0Ac)z , lS% NPMoV/Cl 50°C , 6 11 NPMoV = ~~~Iybdovanadophosphate Kishi, A.; Higashino, T.; Soknguchi, S.; Tefrultcclmnk t t . , 2000, 41, 99.
A \
C 1 0 h1
i-PIOII
,S%j
P ~ ( O A C )20% ~ , Py
toluene , 0, ,60°C
Nishiniura, T.; Kakiuchi, N.; Onoue, T.; Ohe, K.; J. C h m . Soc., Porkin Trans. 1, 2000, 1915.
==? (XSn Bu3
*
A
1%
70%
ClOH21
phv
* JCozMe Bn,NBr, 'ITIF, reflux , 12 h 0
C02Me
Yasuda, M.; Ohigashi, N.; Shihata, I.; Balm & J . Org'. Chenz., 1999, 64, 2180.
>99%
410
Compendium of Organic Synthetic Methods, Vol 11
See also:
SECTION 180:
Section 180
Section 134 (Ethers from Alkt~es). Section 174 (Ketones from Ethers).
KETONES FROM MISCELLANEOUS COMPOUNDS
Conjugate reductions and reductive alkylations of enones are listed in Section 74 (Alkyls from Alkenes).
1. CH,=CIIOBu, a t dppp, NEt, 2.5% Pd(OAc)2, 100"C, 18 h
2. HCl
[bmin] BF4
ionic liquid medium Xu, L.; Chen, W.; Ross, J.; Xiao. J. Org, ,!.eft., 2001, 3 , 295.
MMPP = mgnesiurn inonopemxy phthalate Lee. K,; Im, J.-M. Tetruliedr-on Lett., 2001, 42, 1539. KMn04 , A1203, acetone
Jo
rt,2h
Chrisman, W.; Blankinship, M.J.; Taylor, B.;
m.C.H Tetruhedron Lett., 2001, 42,4775.
1. PhLi, THF, -78"C, 1 d
2. AcOH ,0°C 0 O2N Santos, R.P.; Lopes, R.S.C.; Lones. C..C. Synthesis, 2001, 845.
N-O€I
Nattier, B.A.; Eash, K.J.;
0.5 Bi(NO3h.5 HzO , xi acetone
72~95%
)(
0.1 C U ( O A C ~ * X H2~ hO , Ph Montoniorillonite K-10 * Synthesis, 2001, 1010.
88%
41 1
Ketones from Misc.
Section 180
fin
A.R.; Mallakpour, S.E.; Mohaniinadpoor-Baltork, I.; Khoee. S. Synrh. Coniniun., 2001, 31, 1187 Dour.
B(011)2
A c 2 0 , dioxane , seakd tube /
cat [Rh(CH,=CH2)Cl]2, D M E , 16 h b t . C.G ; Watlsworth, K.J. Clzerii. Cornrnun., 2001, 2316.
2
PhPb(OAc)3
CO, 5
NaOMe, CI-IC13
& /
68%
lph 4
5% P~l(dl1a)~-CIICl~ , MeCN , rt
*
70%
Ph J
A
N-ON
Ph
.. .
[(NO3XCe],-II2IO6 , MeCN reflux, 5 mill
Shlnnl.;Azadhnr, M.R. Synth. Corirrnun., 200Z, 31, 3775. N-01-1
A
Ph
93%
ji
m 1 ( 0 2 c c + F3),
83%
"1 TI-IF ,rt , 40 min Ph P 11 Chen, D.-J.; Cheng, D.-P.; a e n . Z -C, Synrlz. Cornrnun., 2001, 31, 3847.
PEG-NOz, rt , 4 5 h P hZC=N-OH + PhZC=O Liu, X.; %hanp.; Zhang, S.; Zhang, .I. Org. Prep. Proceed. Int., 2001, 33, 87.
w; Ghosh, K. Angew. Cliiwt. Int. Ed., 2001, 40.
"%
412
Coinpendiuin of Organic Synthetic Methods, Vol 11
N41-1
Section 180
(NII4hS20, , A g N Q ,hexane
A
Montinorillonite ,S O T , 2 5 h
Ph
*
98%
Ph
kh3ULM.M.; Kojiina, K.; Yakahe, S.; Morhnoto, T. J. Chem. Re$, (s), 2001, 277. Et4N+Mn04-, neat, 40min
f;-oll
Bigdeli, M.A.; Nikje, M.M.A.; Heravi, M.M. J. Clzein. Res. (S), 2001, 496.
r u
Carter, C.A.G.; Greidanus, G.; Chen, J.-X.; W k e r . . J. Am. Chein. SOC., 2001, 12.1, 8872.
21.2 CsF, KzCO3 2 tq, MtCN BnEt3NCI ,92T
M
~
O
* CO 2M e
10% Pd(PPh3)4, 20% PPh3 0
TBSO
1
Ph Khan, F.A.; Czerwonka, R.; Reissir. H.-1.J.Eur. J. Org. Chein., 2000, 3607. "Me2
A
Pd(OAc)2/SnC12
Ph Mino, T.; Hirota, T.; Fujita, N.;
1
Ph
aq DMF
. ,
75%
Ph Synthesis, 2000, 69.
Ni(l1) coinplex , 0,, Me3CCN0 PhF,Sh
Blay, G.; Benach, E.; Fernrindz, I.; Galletero, S.; Pedro. J&;
c
) ,
90%
Ph Ruiz, R. Synfhesis, 2000, 403.
StankoviC, S.; Espenson. J.H. J . Org. Cltein., 2000, 65, 2218.
I
Section 180
Ketones from Misc.
413
Mitra.;De, A.; Karchaudhuri, N. Synth. Corrrriirtn.,2000, 30, 1651. N-01-1
SiO,-CrO,, toluene
&
75”C, 2 h * I’hph’ itkar. B.M. Synth. Corrrnrrin., 2000, 30, 665.
Ph
.-
Br
. ... ,
B.:
cam’s acid , si02 , ALQI-1
89%
.r
25°C Br
94%
m. M.M.; Ghodrati, K. Syrifh. Conui~iin.,2000, 30, 4501. 1. 2 eqBuLi, TIIF, -78°C + 2. BnBr
Xh
it
G Ph
3.10% oxidic acid, mflux
Dwyer, M.P.; Price, D.A.; Lamar, J.E.; Mev. e&
B
n
Bu
72% (73% ee) Tetrwheclron ,!.eft., 1999, 40, 4765.
1. C O ~ ( C O,)NEt, ~
oN OH
Ph
2. xi MtA31)II
*
-ds
Mukai. C.; Nomura, 1.; Kataoka, 0 . ;Banaoka. M. Syntliesis, 1999, 1872.
”y” Bt
Bt = henZotria70le
1. Pd(OAc), , PPh3, ZnBr2/PhH
2J-(.+J3. II,O, reflux
Katritzkv.;Huang, Z.; Fang, Y. J. Org. Cherii., 1999, 64, 7625.
98%
8090% (96:4E:Zj
Coinpendiuiii of Organic Synthetic Methods, Vol 11
414
0
1% Pd(PPh3), , 1 & n C O DCM,O"C,17h
O C W (=r 'roi
Sakurai, H.; Tanabe, K.; W s a k a . IL, Cheni. Lett., ZYYY, 75.
o=
Section 180
*J To1
71%
C,3h
YYYO
G.-S.; Gong, 1-1.; Ynng, D.-13.; Chen, M.-F. Synth. Coriimun., 1999, 2Y, 1165. zeolite-KMnO,, DCE
N-ON
rt , 3 0 m i n Jadhav, V.K.; Wadgaonkar, D.P.; Joshi, P.L.; Synth. Cnriiniun., I Y Y 9 , 29, 1989.
o=
N -NI-ICONI I2
Gong,
M.;
x
MqNI-I+ Cr0,Cr A 1 2 0 3 , ether , 3 0 inin
G . - S . Synrh. Conintun., 1999, 29, 2591.
Ph Shahi, S.P.;
A
NaIi, T I I F , MqSiOOSiMe, lt,ld
Ph
S>wrh. Conintiin., IY99, 29, 4321.
70%
KIIC03 ,Oxone, acetone PhE=N-NI-IPh
t PhzC=O 45 inin Mahhouhghah, N.Orb. Prcp Proceed. Int. ZYYY, 31, 112.
w,
cil t
Ph3B
98%
Pd(0Ac)z , MeOH ,Oz
25°C. 15 h Ohe, T.; Tanaka, T.; Kuroda, M.; Cho, C.S.;Ohe, K.; Bull. Chetit .Sor. Jpn., I Y Y Y , 72, 1851.
t
Ph-Ph
93%
REVIEWS: "Recent Advances Into The Enantioselective Protonation Of Prostereogenic Enol Derivatives," Eames. J.; Weerusooiiya, N.Tetruhedron A.syiim., ZOUZ, 12, 1.
Section l8OA
415
Protection of Ketones
"Regeneration Of Cwhonyl Compounds From The Comesponding Oximnes,"Corsiiro. A.; Chiacchio, U.; Pistarh, V. Synthesis, 2001, 1903.
SECTION 180A: PROTECTION OF KETONES
meminp.;Funk, L.; Altundas, R . ; Tu, Y. J. Or#.Client., 2001, 66, 6502.
Q
II02CCI10, AniherIyst IS
A
-
miuow aves , 1 rnin
Ph
Ph an. S.P,; Soni, P.; Kamat, S.K. Synlett, 2001, 1251. N4I-I
A
Ph
94%
-(C61 14S02N(BrKH&-
*
CCI4, rt , 2 h
95% Ph
m a z a e i . A; Vagbei, R.G.; Tajhakhsh, M. Tetruhrdron Lett., 2001, 42, 5099. cat TiCld, NEt3,
MeOII
0°C ,30 nun
*
c>
83%
Clerici, A,; Pastori, N.; porta. 0. TetruRedron, 2001, 57, 217. IIOCI12C€12011, 110°C. G h Pt-MoE102catalyst
A+
mv.B.M,; Keddy, V.R.; Giridhar, D. Sjnth. Conmiin., 200Z, 31, 1819.
acetone, x f l u x , cat Bi(OTf),
=
Ph
98%
97%
Mohdmm,ldnoor-Baltcllk.; . . Khosropour, A.R.; Aliyan, €1. Synth. Coninzun., 2001, 31, 341 1.
Coinpendiuin of Organic Synthetic Methods, Vol 11
416
aq acetone , P ~ I ( O A C ) ~
cs
92%
Am
Shi.; Wu, Q.-Q. Synth. Conrinun., 2000, 30, 4081.
Ph
Ph
1.0.1 VOC13, CF3CH20H ,O2 reflux , 5 h
-
2. II,O
Tetruhedron Lxtt., I Y Y Y , 40, 9055.
Ph-c(
HOCII,CI-I2SH, DCM
*
zeolite HS7-360, 1.5 h
. l.nl.,Barhoni, L.; Maggi, K.; Ball
quant Sartori, G . Syntlz. Cornrnun., I Y Y 9 , 2Y, 713.
PhI(OTf), , NaI ,DCM it, 15 inin
Ptl
q"mt
Ph
Kirahara.; Ochiai, Y.; Arai, N.; Takizawa, S. ; Momose, T.;
0-hP
Section 180
-
m>o Ph
91%
Chen.; Wang, 11.-M. Org. Prep. Proceed. Int., 1999, 31, 562. N-NMq Nasreen, A.; &a.
FeS04*7H 2 0 , CIIC13 rt,45min
-
S.B.Org. Prep, Proceed. Int., 1999, 31, 573.
See Section 362 (Ester-Alkene) for the fonnation of enol esters and Section 367 (Ether-Alkenes) for the formation of enol ethers. Many of the methods in Section 60A (Protection of Aldehydes) are also applicalile to ketones.
90%
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 13 PREPARATION OF NITRILES
SECTION 181: NITRILES FROM ALKYNES NO ADDITIONAL EXAMPLES
SECTION 182: NITRILES FROM ACID DERIVATIVES NO ADDITIONAL EXAMPLES
SECTION 183: NITRILES FROM ALCOHOLS AND THIOLS NO ADDITIONAL EXAMPLES
SECTION 184: NITRILES FROM ALDEHYDES
PhCHO
NH3 , MgSO., ,02,16 h
Lai.; Bhamare, N.K.; Anderson, W.K. Synlett, PhCHO
*
12 , NH3/H201 THF , rt ,301nin
Talukdar, S.; Hsu, J.-L.; Chou, T.-C.;
PhCN
2001, 230.
89%
Ph-CN
c
J. -M. Tetruhedron Lerf., 2001, 42, 1103.
96%
CH2(CNh , umtmpine PhCAO
c N CN Yadav.;Reddy, B.V.S.; Madan, Ch. J. CIiem. Res. (S),2001, 190. microwaves, 2 min
P
h
T
87%
Compendium of Organic Synthetic Methods, Vol 11
418
mCN
NH3 ,CuCl , I-PiOH Phm C I I O
J
50% € I 2 0 2 , 3 h
Section 184
Ph
76%
Erman.;Snow, J.W.; Williams, M.J. Tetruherlron Ltt., 2000, 41, 6749. NH2OH *€ICI , NH40Ac m i m w aves , 1 min
92%
Das.;Ramesh, C.; Madhusudhan, P. Synlett, 2000, 1599. NH4HC0, , aq KOH , MeCN , 1 S h @u,N k%Q C W I C W N i ( C o 2 H h
BuCIIO
Chen.; Fu, H.; PhCHO
Bu-CN Meng, G.; Cheng, Y . ;Lii, Y.-X. Synthesis, 2000, 1519. NH20H-HCI , toluene
Bajpai, A.R.; Deshpande, A.B.; PhCHO VeverkovB, E.;
-
Fa280
*
89%
72%
PhCN
Synth. Cornntun., 2000, 30, 2785.
NHzOEI*HCI, 220"C, NEt, phthalic anhydride, microwaves, 3 min
*
PhCN 84%
Synth. Commun., 2000, 30, 3109.
NHzOH.HC1, NMP , 115°C , 5 h PhCIIO * PhCN 86% Kumar.;Reddy, B.V.S.; Reddy, P.T.; Yadav, J.S. Synthesis, 1999, 586. PhCHO
NHzO€14Xl, microwaves
*
NeI-IS04*Si02, 2 min Das.;Madhusudhan, P.; Venkataiah, B. Synlett, 1999, 1569. PhCHO
PhNHC02NH,*TsOH, T H F
reflux W u n . N.; Arikan, N. Tetruherlron, 1999, 55, 11943.
+
PhCN
PhCN
84%
90%
€12NOH*IIz0, 15 inin N-me thylpyrmlidinone Kaur, G. Tetruherlron, 1999, 55, 13265.
98%
Nitriles from h i d e s
Section 186
SECTION 185:
419
NITRILES FROM ALKYLS, METHYLENES AND ARYLS
ClQMe
400”C, cat DC-108 N H 3 , 3/202
* +CN
86%
c1
c1
Oione.;Chi, H.; Guangyong, X.;Chongwen, X.; Yuanyin, C. Synth. Commun., 1999, 29, 2349.
SECTION 186: NITRILES FROM AMIDES
PyBOP , i-Pr,NEt, DCM
* NC
I i 2N0 j - d :
4:
95%
P yBOP = henzotriazol- 1-yloxytris(pyirolidino)phosphoniurn hexaflu5)rophosphate Base.; Narsaiah, A.V. Synthesis, 2001, 373.
K,,,
4 NaOH ,TEBA ,CIICl,
Ph
ultrasound
Sivakumar, M.; Senthilkurnar, P.; Ph/\l(
NH2
=
PhCN
84%
Syntlz. Coinmiin., 2001, 31, 2583.
Cl, c-CI I,Oc<)Cl Et,N
*
0 Bose. D.S.; Kumar, K.K. Synrh. Conirnun., 2000, 30, 3047
84%
Ph-CN
am
P y , < S ” C + r t , S h *MeO MLS OMe Bose. D.S.; Goud, P.R. Tetruheriron k t t . , I9Y9, 40, 747.
OMe
91%
Section 189
Compendium of Organic Synthetic Methods, Vol 11
420
a,,,
B u s n o , microwaves , toluene
90%
PhCN
z
Ph
B o s e . I ) , S , ; Jayalakshmi, B. J. Org. Chem., 1999, 64, 1717.
A A
(CF3S02)20, NEt3 ,r t
c
CH2Clz, 15 min
PhCN
90%
Ph NHZ Base.; Jayalakshmi, B. Syntlwsis, 19Y9, 64.
Bu2Sn0 , toluene
*
reflux
PhCN
86%
Ph NH2 Bose, D.S.; Jayalakshmi, B.; Goud, P.R. Synrhesis, 1999, 1724.
BG
..
\ 1
EDCI , Py ,DCM ,rt * B
r
\ e /C
NH2
N 84%
E m = 1-( 3-dimethylluninopropyl)-3ethyl-Bcarhodiimide hydrochloride b s e . D&; Sunder, K.S. Synth. Cornmun.. 199Y, 29, 4235.
SECTION 187: NITRILES FROM AMINES
PhC€I,NH Gao, S.; Herzig, D.;
M q N O , O S O ,~THF/HzO/Py
*
rt, 1 2 h Synthesis, 2 U U 1 , S44.
PhCN
32%
SECTION 188: NITRILES FROM ESTERS NO ADDITIONAL EXAMPLES
SECTION 189:
NITRILES FROM ETHERS, EPOXIDES AND THIOETHERS NO ADDITIONAL EXAMPLES
Section 190
Nitriles from Halides
42 1
SECTION 190: NITRILES FROM HALIDES AND SULFONATES
2 eq KCN , cat Pd(OAc)2 cat dppp , toluene, 1 6 0* ~
C1
d
C
91%
N
Sundermeier, M.; Zapf, A.; Beller.;Sans, .I. Tc.truheriron Lett., 2001, 42, 6707. [NaBII,CN/cat~holj, K,PO4
PhI
cat Pd(PPh,),/PPh3, TIIF 1xAux. I d Jlane.;Kan, Y.; Zhang, A. Tetrukedron, 2001, 57, 1581.
-
PhCN 7X%
NaCN , PEG400
* C,H+N reflux, 6 h Cao. Y . - 0 . ;Chen, B.-11.; h i , B.-G. Syntlt. Coninnin., 2001, 31, 2203. C4H9-Br
96%
Zn(CN)*, DMF , lSO"C14 h c a t P d , ( d l ~ ),~cat dppf , cat Zn
OMe Jin, €.;Confalone, P.N. Tctrulzedron Lett., 2000, 41, 3271.
OMe
88%
syiingepunp,9 h * CN Bowmun.;Bridge, C.F.; Bsookes, P. Tetruhrdron Lett., 2000, 41, 8989.
/
CUCN , cat Pdz(dl~a),, dppf
M ;.T-
1.
.
\ O/
&
I
TIIF, reflux , 1 h
Ohsawa, K. J. Cherit. Soc., Perkin Trans. I, 1999, 2323.
93%
422
Compendium of Organic Synthetic Methods, Vol 11
Section 193
SECTION 191: NITRILES FROM HYDRIDES NO ADDITIONAL EXAMPLES
SECTION 192: NITRILES FROM KETONES NO ADDITIONAL EXAMPLES
SECTION 193: NITRILES FROM NITRILES
d i
Conjugate reductions and Michael alkylations of alkene nitriles are found in Section 74D (Alkyls from Alkenes).
&
4 eq i-PrCN , KI-IMDS toluene, 60°C. 18 h
Caron.;Vazquez, E.; Wojcik,
*
95%
J.M. J. Am. Ch~in.SOC., 2000, 122, 712.
CHpCHPh , DMSO
-
30% t-huOK, 25°C
CN Orb. Lxtt., 2000, 2, 3285.
Rodriguez, A.L.; Bunlaksananusurn, T.; CII2(CN)2 , 2.2
Ph
~ XC-BUOK J
* Ph--(cN 70% 0.2 NiBr2(PF'h3)2 ,0.4 PPh3 CN 0.6Zn,THF,2d Cristau. €I.It; Vogel, R.; Gillefer. M .; Gadras, A. Tetruh.ec1ronLett., 2000, 41, 8457. Ph-I
6 eq SmI, , T I I F , MeOH PhIIC+cN
Guo, H.;
60T, 6 h Synth. Cornrnm., 2000, 30, 1879.
SO,Ph
*
WCN 67%
Ph
Section 195
Nitriles from Misc.
423
SECTION 194: NITRILES FROM ALKENES Me,C(OH)CN , Ni(cod), , toluene
A
Ph
Yan, M.; Xu, Q.-Y.;
SECTION 195:
NITRILES FROM MISCELLANEOUS COMPOUNDS 2% [KuCl2@-cyineie), , 10 min
Ph\
N-OH
Yang, S.H.;
>98%
chird diphosphite coinplex Ph N C' 100"C, 1 d ' . Tetruhedron Asyrnnz., 2000, 11, 845.
MLCN, MS 4A , 80°C Org. Lett., 2001, 3, 4209.
*
' m i , p Y ,c w 3 N 2 0 3 ,
. .. .. Ghll\LI.; Bakhtiari, K. Synrh. Cornnwn.,
-
94%
Ph-CN
M
e
microwaves
O
O
\ /
C
2001, 31, 1x03.
MLO,(CN) SO,NEt,
* P hCN 66% 2S"C, E M ,2h Jose, B.;Saulatha, M.S.; Pillai, P.M.; Puhpu-L Synth. Cotnniun., 2000, 30, 1509. P hCII=N-OII
feiric sulfate , R H ,reflux
t PhCN 3h P e s a i . D.G,; Swami, S.S.; Mahale, G.D. Synth. Coninlurr., 2000, 30, 1623.
PhCXI=N-OII
81%
hC13, M d N , flux, 1.5 h
* PhCN 98% Barinan, D.C.; Thakur, A.J.; Prajapati, D.; S ~ ~ J & 1 'L Clzern. A Lett., 2000, 11%. P hCI I=N-OH
A N--01I
Ph
SKI,
. I X M ,rt , 15 inin
0)
t
Ph-CN
Chaudhari, S.S.;w n c h i . K.G. Synth. Con~niun.,I Y Y 9 , ZY, 1741.
96%
N 64%
424
Compendium of Organic Synthetic Methods, Vol 11
PhCH=N-NMeZ
Oxone ,wet Al20, , 6 inin PhCN
minuwaves
Ramalinram.~.; Reddy, B.V.S.; Srinivas, R.; Yndav, J.S. Synth. PhCH=N-OH
Section 195
TiCb(OTf), sealed iuhe
Irannoor.~.; Zeynizadeh, B.Synth.
8 0 T , 10 h
-
78%
Commun., 2000, 30, 4507.
PhCN
90%
Cointirun., 1999, ZY, 2747.
EPZ-10, microwaves 68%
6 nun I
B -;P.
c1
c1
Sadavute, V.S.; Sahu, K.R.Synth. Cnritinun., 1999, 2Y, 3409.
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 14 PREPARATION OF ALKENES
SECTION 196: ALKENES FROM ALKYNES
J. Org. C ~ P I O2001, I . , 66, 3176.
Herz, H . G . ; Schatz, J.;
112 , Lindlar catalyst ,DMF diethylenetiiuninc , rt , 18 h
-
Campos, K R.; Cni, D.; Joumet, M.; Kowal, J.J.; Lursen, R.D.; Reider, P.J. J. Org. Chmi. 2001, 66, 3634.
94% (74:26 E:%)
Watanahe, 11.; Terao. J.: h i l i e .
N. 0r.y. I x t t . , 2001, 3, 1733.
93% Chatani, N.; h u e , H.; Morimoto, T.; Muto, T.;
J. 01.8. Chent., 2001, 66,4433.
426
Section 196
Compendium of Organic Synthetic Methods, Vol 11
,THF, rt Lr
HS iMezOSiMe2H t-Bu,P-Pt(DVDS) 2 eq Bu,NF ,rt 5% Pd(dba)z
Denmark.;Wang, Z. Org. Lett., 2001, 3, 1073.
-iSiMe,
5%JdpPFLC12, W E +
1.25 Prahharasuth, R.; Yan V
MqSiCHNz 83"C, 7 h
PMP-S
2 PhI ,574) P d ( 0 h ) z NaOAc, Bu~NCI,DMF
P-h
100°C , 1 d
Larock. R .C, ; Tian, Q. J. Org. Chenr., 2001, 66, 7372.
1. TBDPSCl , imidamle DMF, rt
-* 62%
OTBDPS
2.2% Pd~(dha)3*CHC13 ,AcOH OAc 23% PPh3 , toluene, reflux El-Sayed, E.; Anand, N.K.;
Et
=
Et
78%
w J. Vrg. Chern., 200Z, 66, 5256.
85%
OAc
Org'. Lett., 2001, 3, 3017.
Et+cqEt YCozEt
S% I Pd(0Ac)z
AgzCO3, MeCN 20°C , 3h . Kotora.; Matsumura, H.; Gao, G.;
Et Et Org. Lett., 2001, 3, 3467.
72%
Section 196
Alkenes from Alkyncs
427
10% W(CO)j*'INF ,THF 3 eq EtOzC
ph
H20
C4Et
CO,Et
. ., K.;Kusama, 13. Org. Lett., 2001, 3 , 3871. IWdSclWrl.Maeyania,
CqEt 99% (>95:5 exo:endo)
I
w
DME 'heat
0
65%
Ajamian, A,; Gleason. J.1,. Org. kn.,2001, 3, 4161. I
.C02Me
*(:If&
-m
6%Me,SiCl, Kl' 1 1 h cat TBAF, PMHS , ether l%PdC&(PPh,)2,1% Pd,(dha), 4%J(2-furyl),P , 37°C; Maleczka Jr.. R.E.; Gallagher, W.P. 01-8.Lett., 2001, 3, 4173. 6% Me3 S 11C1 WABr
1 %PdClz(PPh3h ~
,CW" (CIIZh 73 %
CbPh
1% Pdzdha3,4% (2-fuyl)3P * aq Na2C03 , PMIIS , ether Ph 90% 3 7 T , 15 h Gallagher, W.P.; Terstiege, I.; M&& a Jr.. J. Ant. Cheni. SOC.,2001, 123, 3194. 011
C,II~
=
Cd17
1 % KU catalyst, CII2C12
(EtO),SiII
-
Trc,st. B.M,; Ball, Z.T. J. Am. Clicwr. Soc., 2001, 123, 12726.
Si(OEt),
~ ~ 1 - 1 ~
Jb 99%
428
Section 196
Compendium of Organic Synthetic Methods, Vol 11
c6H13-
a t Pt(PPh3)4, 15 h
- GHh 77%
PhS fi toluene, flux PhS Ph Sugoh, K.; w vasu. H.; Sugae, T.; Ohtaka, A,; Takai, Y.; Tanaka, A.; Machino, C.; Kamhe. N.:Hurosawa. H. J. Am. Clwm. SOC., 2001, 123, 5108.
Mqsi
Me3Si
)
SiMe,
I
,ether, 5 h
1. &Br
2 q Ti( Oi-Pr).J2 i- PrMgBr - 1 5 " C d -40°C 2. €130'
Me$; Okamoto, S.; Suhhnraj, K.; Sato. F. J.
C3H7
=
Airi.
Clzeni. SOC., 2001, 123, 4857.
PhB(OH)2, xi dhxane
c3 137
h
3% K h ( i ~ ~ ) ( C z H 4 )dppb 2, 87% * C31J7 C3HF lOO"C, 3 h JIavashi. T.; Inoue, K.; Tankguchi, N.; Ogasawara, M. J. h i . Chern. SOC., 200Z, 123, 9918.
BUOII ,2%Pd(OAc)2 2.5%phosphine ligand toluene, 2.5 eq Cs2C03 Asao, N.; Shimada, T.; Shimada, T.;
Yalnalnotc3 . Y, J. Ant.
MqSiI , toluene -50°C
+
Clzerit. SOC.,2001, 12, 10899.
OMe +
OMe
10°C
82) 84% OMe (18 Takami, K.; Yorunitsu, H.; Shinokuho, H.; Mntsuhara, S.; Q s h i m a Synlett, 200Z, 293.
Section 196
Alkenes from Alkynes
429
HSiCI, ,20"C, 18 h
1% [P~CI(JC-C~I-IS)]~ PFFOMe
H
tBu,,,
a,si+L'==(
*
81% (72% e e , S) Vo-Tranh, G.; Boucard, V.; Sauriat-Dorizon, 14.; GuihB. F. Synlett, 2001, 37.
Me
Ackermann, L.; Bruneau, S . ; Pixneuf. P.H. Synlett, 2001, 397. Ph
MLCN , 130"C, 18 h
Ph,P (0 100) 95% (95 5) 90% Kazankova, M.A.; Efirnova, I.V.; Kochetkov, A N . ; Afanas'ev, V.V.; Beletskaya, I.P.; Dixneuf, P.H. Synlett, 2 0 0 1 , 497.
+ N i ( a ~ a c )(EtO),PH=O ~,
PI
58%
cI4
Prakash, 0.;Shiinna, V.; Butra, €1.; jl4oriarty. R.M. Tetruherlron LL".,2001, 42, 553.
5%JPhCII(0Meh TlClOd, CH2Ch
-5O"C, 2 h
-
I'hM %
Me quant Niimi, L.; Shiino. K.; Hiraoka, S.;yokoz awa. T. Tetraheriron Ixtt., 200I, 42, 1721.
-
-
1 . 10% Fe(acacb , 3 eq Bu1-i. To1
2. IN IICl
Hojo, M.; Murakami, Y.; Aihua, 11.: Sakuragi, R.; Baha, Y.; Angew. Chern. Int. Ed., 2001, 40,621.
Bu
n 97%
-
430
Compendium of Organic Synthetic Methods, Vol 11
Section 196
S% Gmhhs' catalyst l h , PhH
Smulik, J.A.;
Tetrah~~drori Lett., 2001, 42, 171.
HSiCI3, 20"C, 18 h 1% [PdCl(n-C3H~)]2
H Me
Han, J.W.; Tokunaga, N.; Ph
=
COZMe
81% (72% e e , S) ash i. T, J. Am. Clwni. SOC., 2001, 123, 12915.
m
112 , Pdpuinice , EtOH .r
CD2Me 96% Ph cat ethylenediarnine , 12min GlllttdddUTid.; * . . Liotta, L.F.; Noto, R.; Deganello, G . Tetruhedron Left., 2001, 42, 2015.
[Ti(Oi-Pr),/2 i-PrMgCl] ether, -50°C
.-, -20°C
*
80%
0Me Delas, C.; Urahe, H.; Sato. F, Tetwheriron Lett., 2001, 42, 4147.
L;arock.; Yue, D. T~mdiedronLett., 2001, 42, 6011. 5 % Pd(PPh3)4, I'HF, 2 h
F3C
PhZnCl ,0°C -+ rt
F3
*
Konno.; Tanikawa, M.; Ishihara, T.; Yamanaka, €I. Clzezent. Lett., 2000, 1360.
ph
77%
Section 196
Alkeiies from Alkynes
43 1
at Pd(OAc)z/PPh,
McONa , MeOH 25"C, 1 d
Ph OMe OMe M.-.I,; Wei, L.-M.; Lin, C.-F.; Leou, S.-P.; Wei, L.-L. Tetralzerlron, 2001, 57, 7839.
qPh 5% [Rh(diphos)Cl], , DCE AgShF6 , rt , 2 11
Cao, P.;
Angcw. Chenz. Int.
Ed.,2000, 39, 4104.
62% (96% ee)
t-Bu,CuLi-LiCN , PBu,
-xo"c
t-Bu
Krduse.; , . Purpura, M. A n g w . Chun. Int. Ed., 2000, 39, 4355.
92% (25:75 E:Z) Ph
/ph
10% PhI,PPh3,5 5% Pd(OAc), eij N ~ O Ap:C p /h
NEt, , D M F , X0"C , 2.5d Ph
Dvker.-; Bomwski, S.; Henkel,
Ph G.; Kellncr, A,; Dix, 1.; Jones, P.G.
Tetrcrhedron I x t t . , 2000, 41, X259.
53%
Coinpendiuin of Organic Synthetic Methods, Vol 11
432
y e
I
Section 196
Me
cat [Rh(bisphosphine)Cl]2 DCE,rt,lh
* PhO2S
Wang, B.; Cao, P.;
Tetruhedran Lett., 2000, 41, 8041.
10% PPh, , 2 h
2 eq ALOH , toluene 10 eq Et3SiI.I, S O T
t
(70% Qh. C.H.; Han, J.W.; Kim, J.S.;Um, S.Y.; Jung, N.H.; Jang, W.11.; Won. H.S. Tetruheriran Lett., 2000, 41, 8365.
73% (14:lE:Z)
Madine, J.W.; Wang, X.; m n h o e f e r . R . h Org. IAtt., 2001, 3, 385.
Fernindez-Kivas, C.; M h d e z , M.; E & i w m x n . & J. Am. Chein. Sac., 2000, 122, 1221.
433
Allcenes from Alkynes
Section 196
60 psi C I f 4 I I 2 , DCM, 22 h
\&hp
cat Clz(FCyzhRu=CHPh , rt
phk 78%
Smulik, J.A.; Diver.. ' ' J . Org. Chem., 2000, 65, 1788.
&lori. M.; Kitamura, T.; Sakaihara, N.; Sato, Y. Org. Lett., 2000, 2 , 543.
aP y
LDA ,TfIF , rt
[2°zh4e *
I
76% (94:6)
jlarada. T.; Fujiwara, T.; Iwazaki, K.; Oku, A. Org. Lett., 2000, 2 , 1855.
1 .Bu,SnII, PhIi, rellux syringe , AIBN pump
~
-
2. icflux, satd K F , r t , 2 h
s
~
,
M
41: 75%
0 $ha. C.-K ; Zhan, 2.-P.; Wang, F.-S. Org. Lett., 2000, 2 , 2011.
BrQE:
KO11 , toluene, 15 niin
-
( C ~ H I ~ ~ N*T J ~
Br Oku, M.; hral.;Katayarna, K.; ~ S y r t l c ~ t2000, f , 493.
Ph
H
e
434
Coinpendiuin of Organic Synthetic Methods, Vol 11
1 . 2 eqNsNC12, 2eq NsNHNa 10% CuOTf
Ph*C02Me
2. aq Na2S&
L Ph
*
Section 196
C
Q
M
e
i
x
N HNs 76% (20:1 anti:syn)
Li, G.; Wei, 11.-X.; Kim, S.H. Org. Lttt., 2000, 2, 2249.
-
1. f-BuLi ,-78°C r t , ether 2. CI-I,=CHPh (syringe pump)
\b
Et
ether, rt ,5 min 3. MeOII
*
PE Ph
61% (97:3 E:Z)
Wei, X.; Tavlor. R.J.K, Angew. Cheni. Int. Ed., 2000, 39, 409.
IIC&COZEt, 10% Pd(0Ac)Z TFA , E M , rt
4.5% ( U E = 2)
Jia, C.; Lu, W.; Oyamada, J.; Kitainura, T.; Matsuda, K.; Irie, M.; J. Am. Chenz. Snc., 2000, 122, 12.52.
2 eq NgHSiMe, ,dioxane
M -eP
* Me,Si
5% RuCl(cod)(CSM%), 60°C
4
SiMq
Ph 56% Le Paih, J.; Dhien, S.; Ozdemir, I.; Dixneuf. P.H. J. Am. Chern. Soc., 2000, 122, 7400.
Zhang, Q.; U
J
. Am. Cliem. Snc., 2000, 122, 7604
Section 196
Alkcnes from Alkynes
Chatani, N.; Inoue, H.; Ikeda,
GH13-f
435
‘I’.; Murei.S..Org. Chm., 2000, 65, 4913. OC02Me
MqSiCN ,576 Pd(PPh3),
DujLX-Tankguchi,
oi
(-=JI“
5-
TIIF, reflux , 1 h
NC 91% M.; Yasuda, T.; Kawamura, T.; Ohora, Y. Org. k t t . , 2000, 2, 2635.
Ph-
N
CO2Et
Pd(OAc), , ALOH , It
I1
&
C4Et
*
Lu, W.; Jia, C.; Kitamura, T.; b w n r i i . Y. Org. I z t t . , 2000, 2, 2027.
78%
Plla tTHF Cp*RuQ(cod) 60h , 80°C CO,Et* ; -$m & Q -$
.
Ac 0 Jordan, R.W.; Tam, W. Org. Lett., 2000, 2, 3031.
Ph
=
PhI, 5% Pd(OAc)2 10% PPh3, DMF
Ph 2
~ X NaOAc, J
100°C
Bu~NCI
.
X
1. B u S K l . KF PMI-IS cat TEAF ,‘Pd(PPh,),
TIIF, ink-rowaves 2. Pd(PI’h3)4 lnicl~waves
-
62%
Tian, Q.; h o c k . R.C., Orx. Lett., 2000, 2, 3329.
t-Bu
ACO
Ph
t-Bu
Maleczka Jr., K.E.; Lavis, J.M.; Clark, D.11.; Gallaagher, W.P. Org. L.ett., 2000, 2, 3655.
86%
436
Coinpendiuin of Organic Synthetic Methods, Vol 11
Section 196
Bn-Y SiMe,
Bn-
N
1. 1.5 y (qz-C&)-Ti(Oi-Pr)z
/
*
\:;:
80%
ether, -30°C
Urahe, H.; Nakajiinu, R.;
SiMe3
01-8.Lc.rt., 2000, 2 , 3481. ,SiMe3
54%
Sudo, T.; Asao, N.;
J. Org. Chern., 2000, 65, 8919. 5 % ~( ( I I ~ - C ~ H ~ ) P ~ C , 2Id] Z 10%dppf , toluene, 70°C
= - uB
Bu
.
58% Radhakrishnan, U.; Gevorgyan, V.; Y;Unjlllloto
e
S
i
M
e
3
Bu
Tetruhedron Lett., 2000, 41, 1971.
SiMq
, DCM, rt
Gr uhhs' ca tal ys t Stragies, R.; Voigtmann, U.;
*
69% (1.9:l E:Z)
Tetruhetlron Lett., 2000, 41, 5465.
1. Bu3SnH,AKBN, PhH 7.6mM
2. PITS, DCM
?!d 54%
COzEt
Robertson. J,; Lam, H.W.; Ahazi, S.; Roseblade, S.; Lusch, R.K. Tetruhedron, 2000, 56, 8959.
Section 196
Alkenes from Alkynes
P h =
6
437
0
85"C, 96 h
92% Kawakami, Y. Cheni. Commun., 2000, 1573.
Tsuchirnoto, T.; Maeda, T.;;-
=
wo
F O B 1 1 II2,30rnin
3% Pd/purnice
&
OI'BDMS
OTBDMS 90%cis Gruttadauria. M.; Noto, R . ; Deganello, G.; Liotta, 1.I. Trtruhedron Left., 1999, 40, 2857. 0.1 BuLi/O.l CI12(COzMe),=
'IFIF, reflux, 5 h
COzMe
86%
Et0 C02Me
Kitagawa, 0.;Suzuki, T.; Fujiwara, 1%; Fujita, M.; Taeuchi. T. Teteruherlron k t t . , 1999,40, 4585. EOZC Efy--
: ( F e , ) 2
*
E0,C 97% Sturla, S.J.; Kahlaoui, N.M.; J3uchwald. S.L. J. Am. Clzcm. Soc., 1999, 121, 1976.
P h = Fujiwara, N.;
0.6 eq (CM,=CIICI-Iz~Inz13
TI IF
*
>to. Y , J . Org. Clrcvrr. 1999, 64, 4095.
A
/
94%
43 8
Compendium of Organic Synthetic Methods, Vol 11
Section 196
SiMe, 0.5 EtAICI2 , CH2C12
* 69%
-78°C
J. Am. Chern. SOC.,1999, 121, 3797.
Asao, N.; Shimada, T.;
(>97
3) 97%
maps, E.; Schmid. W, J. Or-g. Cltcvn., 1999,64, 7537
-Rw"'
1. Cp,ZrEt,
-Ph
2.12
3. CUCl
Tdkdhashl.; . . . Shen, B.; Nakajima, K.; Xi, Z. J. Org. Chenz., 1999,64, 8706.
Cp*2YMe--THF,rt
64%
*
PhSiI-13,1 d
Molander. G.A.; Corrette, C.P. J . Org. C h w . , l y y y , 64, 9697. PhCBCH , [(~~aphth)Rh(cod)] BF, DCM , 15°C. 15 inin Paik, S.-J.; Son, S.U.; Chvna. Y.K.Org. Lett., 1999, 1, 2045.
B u,cULi*Lil, ether 90%(67:33 E:Z) PUrpUrd, M.;
Eue .I. Org. Chem., 1999,267.
BU
Section 198
Alkenes from Alcohols
COZEt
o
1. PPh3 E M ,
CO2Et
o
NHPh
L
Eto2c+
NHPh
2. PhH , re!lux 3. toluene , reflux
Yavari. L;Asghaii, S. Tetruhedron, 1999, 55, 11853.
de Marigorta, E.M. J.
;-
439
Chciii. Soc.,
92~53~43%
Perkin Truns. I, 1999, 889.
REVIEWS: "Metal-Mediated Carhometallation Of Alkynes And Alkenes Containing Adjacent Heteroatoms," A.G.; Forgione, P. Tctruhedrori, 2001, 57,5899.
SECTION 197: ALKENES FROM ACID DERIVATIVES NO ADDITIONAL EXAMPLES
SECTION 198: ALKENES FROM ALCOHOLS AND THIOLS 1 . MeMgCl, 'ITIF, it, 10 h C
d
r
l
~
~
c
'
2. N iK, NE14C1
u; Shook, B.C. Tetr-ufierlron Lett., 2000, 41, 8847. Saito, S.; Nagahara, ;.'l
Synlett, 2001, 1690
71% (1:l E:Z)
440
Cornpendiuin of Organic Synthetic Methods, Vol 11
Ph,P=CI-ICO$t, DMSO
+
mCqEt
o-iodoxyknwic acid, 1.5 h P hCH, OH
Section 199
*
Ph
98%
Maiti, A,; Yadav. J.S.Synfh. Conintun., 2001, 31, 1499.
=/FC EtO2C
Ph,P=CHCO,Et M I I O ~DCM ,
Br Wei, X.; Tiaylor.
Br
U J. Orb. Chcin., 2000, 65, 616.
Schmitt, A.; &&3ig
70% (40:60 cis:fruns)
H. -IT. Eicr. J Org. Chein., 2000, 3893. Ph,P=CI.IO,Me, MnO, ,DCM .t
toluene ,rt , 4 h Blackhurn, L.; Wei, X.; LyhAiJL
Chern. Coniinun., IYY9, 1337.
80% (>99% JZ)
SECTION 199: ALKENES FROM ALDEHYDES CHPh
11
bJMe
Me / \ , p v y
Me
PhCHO ,THF, r t , 15 inin
*
E-selective
mPh
Ph
91%
Wang, Z.; Zhang, G.; Guzei, I.; Verkade. J.G. J. Orb. Chein., 21)0I, 66,3521.
YHO Bu,P=-/
OB n Harcken, C.;
C0,Me
DCM , toluene
*
Org. Left., 2001, 3 , 3591.
FCo OB r
78% (91 : 9 ErZ)
Section 199
Alkenes from Aldehydes
44 1
7’NSCH=N,, DCM
P hCI I 0 Dias, E.L.;
t
1-296 Rh catalyst ; White, P.S.
J. Ain. Cliein. Snr., 2001, 123, 2442.
InC&-Zn , MLCN , 8h 1cflux
FhCIIO
62% 1:3.7 ( E Z )
I’h -0TMs
e
l’hM +
P h d p h
Ph
(98 Barman, D.C.; Thakur, A.J.; Prajapati, D.; Sandhu. ,I S . Synlett, 2001, 515.
2)
93%
EtO,CCII,P(O)(OEt), , NEt3
PhCHO
b h&C02Et 8 Kbar . M&N . 1 d €Ias-Becker, S.; Bodmann, K.; Kreuder, R.; Santoni, G.; Rein, T.; Reiser. Q Synlett, 2001, 1395.
c:110
1. L.iCI12SiMe3 * M 2. Et,NCI , aq TIII:
c
O
q
\ /
85%
s
M
e
3
86% Kwan, M.L.; Yeung, C.W.; Breno, K L . ; poxsee. K.M. Tetrulzerlron k t t . , 2001, 42, 1411.
c
C I I o KIIMDS , toluene, rt
A.B.;
PhCtIO
pyrc)zs -onps\q\
onPS
(91
Berthelette, C . ; St.-Martin, D. Tetruherlrnn Lcjtt., 2001, 42, 5149. 1. MeN02, AcOII-NH~UAC 100”C, 3 h
mEt
*
Ph
2 . BEt,, Et20-1120 Liu, J.-T.; Yao. C.-F. Tetrulierlron Ixtt., 2001, 42, 6147
P hCI I 0
9 ) OTIPS 67%
M K O z E t , I’(KNCII2C€I2),N
*
i-BuCN , 40”C, 2 h Tmulicdron, 2001, 57, 8047. Kisanga, P.; D’Sa, B.; Verkade. .I.
79%
I > h m C 0 ” ‘ 96%
Coinpendiuin of Organic Synthetic Methods, Vol 11
442
LiOt-Bu ,hexane , Z " C , 1 h Petroski. RJ,;Weisleder, D. Synth. Coiiimun., 2001, 31, 89.
I
Section 199
93% (En=140)
CHz(C02Ilh ,EOAc ,35h
cHo
CH=CHCOzH
graphik , ultrasound, 43°C
u; Zang, 11.-J.; Fang, .I.-Y.; Li, 1.4.;
77% Li, T.-S. Syntli. Conrrizrtn., 2001, 32, 653.
10%PhCHO , 10%Sn(OTf)z DCM, 0°C , N iiiin
ph+
76%
Nokami.; Anthony, L.; Sumida, S.4. Clienr. Em. J., 2000, 6, 2909. [ (PhO~P(O)CII~COzEt, DBU
PhCfIO
N d , 2 HMPA , -7X"C, 2 h J -78°C
-z
0°C
*
PhC C 0 , E t
86% (93:7 Z E ) Ando. K.; Oishi, T.; Hirama, M.; Ohno, H.; Ihuka, T. J. Org. Chern., 2000, 65, 4745. AlC13-Zn ,M&N ,ixflux PhCIIO
10 h
*
92% (99:l E:Z)
Dutta, D.K.; m a r . D, Tetruli~~rlron Lttt., 2000, 41, 6227. PhCIIO, KIIMDS ,THF I ~ C I D W L I -7X"C, -6, 1h OCH,CF3 OCHZCF3 Yu, W.; Su, M.; Ph-Crro
Tetruhedron ,!,eft., 1999, 40, 6725.
CHI3 , cat CrC13(thf), Zn , Me3SiCl , dioxane 25°C ,4h
Takal.;Ichiguchi, T.; Hikasa, S. Synlctt, 1999, 1268.
95% (100% z)
phw I
84% (955 E Z )
Section 201
443
Alkenes froin Amides
TMG = N,N,",N-tetranethylgmnidium
/
OZN
~ A . G . MCramp, . ; S.M.; Roherts, R.S.; Zecri, F.J. 01-8.Lett., 1999,1, 579.
Related Methods: Section 207 (Alkenes from Ketones).
SECTION 200:
ALKENES FROM ALKYLS, METHYLENES AND ARYLS
This section contains dehydrogenations to fonn alkenes and unsaturated ketones, esters and amides. It also includes the conversion of aromatic rings to alkenes. Reduction of aryls to dienes is found in Section 377 (Alkene-Alkene). IIydrogenation of aryls to alkanes and dehydrogenaticlns to forni aryls are included in Section 74 (Alkyls from Alkenes).
1. LDA lTMSCl 2. NBS , -78°C 3. TBAF , -78°C
TMS Dumeunier, R.;
-
OB n Tetrukrrlron Ixtt., 2000, 41, 10219.
SECTION 201: ALKENES FROM AMIDES Related Methods:
Section 65 (Alkyls from Alkyls). Section 74 (Alkyls from Alkenes).
NO ADDITIONAL EXAMPLES
OBn
Section 203
Coinpendium of Organic Synthetic Methods, Vol 11
444
jY
T6r
SECTION 202: ALKENES FROM AMINES BnO
hi-N
CHZ=CIIMgBr, THF BnO GOT,3h
-
N-AZi Bi'
Azi = 2-phenyl N-aziiidinyl group Kim.; Ohi, D.1-I.; Yoon, 1.-Y.; Cheong, J.H. J . Aiiz. Cl?Ci?t.SOC., 1999, 121, 5330.
89% Lee, K.; Kim, Y.H. Synrh. Conmun., I Y 9 9 , 29, 1241
SECTION 203: ALKENES FROM ESTERS
EtCu(CNXMgCI), 0°C Ito, M.; Murugesh, M.G.;
83%
4%
5%
EtMgCllcat CUCN, -18C 86% ' Tetruhedron Letr., 2001, 42, 423.
0 gh I
0
\
= toluene, heat
FaurC-Tromeur, M.; Zard. S.Z. T~~tr-ulzr~~Iron Lett., 1999, 40, 1305.
*
98%
445
Alke~iesfrom Ethers
Section 204
OMe
id
)$
10% Mo(CO),(ECN)~M e o ~ 15% c h i d bis-ainkle
0
*
NaII, CHz(C0zMe)z TIIF, 70°C
COzMe
; m /
(5
94%1W
Glorius, F.; E&T-A 01-8. .!At., 1 9 Y Y , 1, 141.
SECTION 204:
0
ALKENES FROM ETHERS, EPOXIDES AND THIOETHERS
(MezN)2P(O)Cl, IizO lSO"C, 30 inin
-
92%
Tetruherlron, 2001, 57, 227
Rlehi.;Bovicelli, P.; Sperandio, A. Zctrultcr/r.on,2000, 56, 1731.
p, N
I
I
Boc
1. NCS ,CCI, ,reflux , 3 h 2. mcpba , r t , 18 h
t
66%
D.L; Beck, E.X. J. Org. Clwnr., 2000, 65,8367
6.9'
COzEt
LiI ,.4mherlyst-15 , acetone rt,(lh
CSJIll
Antonioletti, R.; Bovicelli, P.; Fazzolari, E.;
* /
CSH11
80%
Zetruhedron k t t . , 2000,41,9315.
Compendium of Organic Synthetic Methods, Vol I1
446
Co salen complex 10 eq Na(IIg)
quant (NMR exp)
THF , 6 h Tetruhcdron Lett., 1999,40, 8747.
Isohe, H.;
Section 205
Jacoh, J.; m e n s o n . J K Cllerrl. Corllrlrun., 1999, 1003.
SECTION 205:
ALKENES FROM HALIDES AND SULFONATES
&j C02Me
I
I-C02Me
,MrCNPd(OAc)z, C ~ 2 c O 3IEflUX , tn-2-biylphosphine norhornene
62%
m e n s . M.,; Pacpin, J.-F.; Piguel, S.; Dahlmann, M. J. Org. Chem., 2002, 66, 8127.
Bu
SiMe3
1. ~
X C ~ SS Sd
2 , TIIF, I E ~ ~ U X
2.0.1 M aq HCl c1 m c e l l b n . J.M.; Bernad, P.L.; Bardales, E. Org. Lett., 2001, 3, 937. I
u M : s %
Pd(dhil)3*CIIa3
(CIl2=CHk h C l 1.5% P(2furyl)3 TIIF/H20 Ixtlux, 3h Takami, K.; Yorknitsu, 13.; Shinohulo, H.; Matsuhwa, S.; Org. Lett., 2001, 3 , 1907.
+
%: : =
c:dBr 1.
PPh2
PhCHO , toluene, 150°C 2. aq K2C02, 125"C, 51nin Westman. J. Org. LLtt., 2001, 3. DMF, 3, 3745. lXO"C, Smin
96% (>98% z)
Section 205
-
447
Alkeiies from Halides
p1 =q3= 5% CIIQ3, r t , 1 d
Bao, M.; Nakamura, H.; -()to.
80%
*
407;PPh, Y, J. Am. Clwni. So(-., 2001, 123, 759. CiCb-LiAlII, , CPrOII
M
* Ph TrrF, DMF 97.5% Oinoto, M.; Kato.; Sogon, T.; Mori, A. Tetrulrcdron Lett., 2001, 42, 939. C1
Ph
,OBn
Ar
CII2=CIISnBu3 , 2 eq KF
5% Pd(T'Ph,)4, toluene 110°C. 30 inin Synlrtt. 2001, 1557.
Ph
Chant..;I s e , M.;
90%
* Ph
Br C02H
NEt, , DMF ,I ~ ~ C I X ) W ~ V ~ X ~
Ph
95% (>99:1Z : E )
Br
P h / y 30 st?c Br Kuang, C.; Senboku, 11.; Tokuda. M Tetrulzerlvon D r t . , 2001, 42, 3803.
HMPA, 100°C
rBrB
100 torr
c
'
W
D
r
78% Van Veidhuizen, J.J.; Vos, T.J.; Zhao, P. Synth. Cornnzun., 2001, 31, 1367.
H;-
To11 IN
K/\ Br
hv , MeOH ,30 inin
-
PPh
TolIJN
0
Ph
75%
Aruna, S.; Kalyanakumar, R.; Ramakrishnan. V . T . Synth. Coritnricn., 2001, 31, 3125.
IIMPA , 160°C , N2, 15 inin ) .
Br
IlMSff
Khurdnd.; . . B:insal, G.; Chauhan, S. Bull.
mPh
Ph
93% (97:3E:Z)
Chmi. Soc. Jpn., 2001, 74, 1089.
Coinpendiuin of Organic Synthetic Methods, Vol 11
448
Section 205
MqSiCII=N2 , C€ICI3 2.5% Pd,(dha):,CHC& 15% AsPh3, i-PrNEt2 rcflux , 12 h
MeOZC Greenman, K.L.; Carter, D.S.; Van V
Br
Ph
0
Claphain, B.;
*
f l 6 %
Meozc
Tetruherlron, 2001, 57, 5219.
CHZ=CHSld3u3 , 2 % Pd,(dha), 20% t1i-2-fuiylphosphine , NMP
-Ax-
6 S T , 16 h
Ph
0
Ph
98%
J. O r g . Clwm., 2001, 66, 9033. Et
$1:
CpzZr
FA
Ph+cl
,
50°C. 12h , TIIF 2.5 DMPU, 2 eq CuCl
c1
63 %
*
Et
Ph +Et
Et
Duan, 2.; Sun, W.-H.; Liiu, Y.; Takahashi. T. Tetr-uhedronLett., 2000, 41, 7471.
Ulerstiuk.; Roy, C.D. Tetrulichm Lttt., 2001, 42, 325.5.
L
Ph
a
Fe ,MeOII ,reflux, 30 min
-
* Ph
ph
Br Thakur, A.J.; Boruah, A.; Baruah, B.; Sandhu. J .S. Syntlz. Coinntiin., 2000, 30, 157. DAI3CO. Br,NCl
Jefferv. 1'.Tctruherlmn Lctt., 2000, 41, 8445.
90%
Section 206
449
Alkenes from I-Iydiides
L€%
mPh
Sm/TIIF , TMSCl (trace H 2 0 )
Ph
5h
Br
Xu,X.; Lu, P.;
' i r
.
LZ. 1
*
82%
Ph
Y. Syntlz. Corrmrtn., 2UU0, 30, 1917. Me2C=C€IMgBr,20°C 3%)L~,c~c& ,TIIF
4 tr]NMP G.; Chaboche, C.; JCzCquel. M. Tetruhedrnn, 2000, 56, 2733
Ct-I2=CI-ISnBu3, I t 5 % ~Pd(PPh3)4, DMF 10%)CuI, A r
/N+
Barchin, B.M.; Valeiiciario, J.; Cuadro, A.M.; Alvarez-Builla, J.; Org. k t t . , I Y Y Y , 1, S45.
/ Vaouero...J. I
CH2=CI-ISllBU3 ,80"C l.S%J Pdz(dba)3, 6% P(t-Bu)3 2 . 2 ~ CsF 1 , dioxane , 12 h
87%
Littke, A.F.; Fu. G . C : . A n p w . Cherii. Int. Ed., I Y Y Y , 3 S , 2411
83%
Br Kim, M I . ; Wei, H.-X.; Willis, S.;
4
C02Et
C02E t
I . Br-Br
Syntlz. Corriniun., ZYYY, 29, 4179. , NaII, DMF
2. DBU ,75-XOoC
sa2 a2Et
Dunce.;Bums, S.E. 0 r - g . Prcp. Proceed Int., 1999, 31, 99.
SECTION 206: ALKENES FROM HYDRIDES For conversions of methylcnes to alkenes (RCH2R' 200 (Alkenes from Alkyls).
RR'C=C€I2), see Section
70x5276
450
Compcndium of Organic Synthetic Methods, Vol 11
Section 207
NO ADDITIONAL EXAMPLES
SECTION 207: ALKENES FROM KETONES
89% (56:44E:Z) J. Org. Chern., 2001, 66, 2990.
Rele, S.; Talukdar, S.; Banerji, A.;
1. BuCnCOLi, -78", THF
H 87%
2. IF, I'hH, reilux
E 1 O l C p C H O
1. LDA ,
P0(0&)2
*
81%
2. Ac@ 3. NaH
OAc
l(raus. G.A.; Jones, C. Synktt, 2001, 703. Copt
1 . Li , Naphth ,-78°C , 0 5 h 2. 0°C , 30 nun 3. henzophenone , rt
* Bu)(:"H
Shlndo.;Koretsune, R.; Yokota, W.; Itoh, K.; Shishido, K. Tetruherlron k t t . , 2001, 42, 8357.
A
1. EtS02Ph, BuLi
Ph
-L
2. Na(IIg) Bu 3.5% HMPA, Sm12 TIIF, 0°C , I h Mrllk6.; .. Murphy, F.; Kumps, L.; Ales, A.; Touillaux, R.; -; S . Tetruherlron. 2001, 57, 2609.
Bu
89%
86~69%
Carhallares, S . ; Dolan,
Alkenes from Nitriles
Section 208
-m 45 1
1 1 . 2 eq BuLi , ether, --78"C, 1 h C3H7 2. ~yclohexanone,-78°C , 3 0 mill
GH7
I
C3H7 75%
GH7
u; Song, Q.; Chen, J.; Gum, 11.; Li, P. Angew. Cliein. Int. Ed., 2001, 40, 1913. 1. K I I ,TIIF, 0°C , t-BuSiMe,Cl 2. 3.3 eq LDA , THF ,0°C
Ph+
3 . 3 . 5 e q TMSCl Ph
pk ,,,urSiMg
*
Ph
84%
SiMe3
bl&riL; Di-iring, M.; Seyferth, D.; Giirls, I-I. Chein. E w . J., 2001, 8, 573.
58% (89:11 , E:Z) Takeda. T.; Takagi, Y.; Saeki, N.: Fujiwara, T. Tetruhedron Lett., 2000, 41, 8377.
Related Methods: Section 199 (Alkenes from Aldehydes).
SECTION 208: ALKENES FROM NITRILES Br
Ph
CN
'111-, XI xTHF
-
*+p
Ph
X
69%I X=Me 73% Yoo. B . - K ; Lee, S . 4 . ; Choi, K.-1-1.;Keuin, S.-K.;KO, .[.-.I.; Choi, K.-I.; Kim, J.-H. Tetrulierlrnn I x t t . , 2001, 42, 7287.
X=II
Compendium of Organic Synthetic Methods, Vol 11
45 2
#
-0
1.5 eq CII2=CHMgBr, 1 h 1.6 CXIAgBF, ,-78°C
+
Section 209
0°C
Ph Agami,C.; Coutv. F,; l h n o , G. Org. Lett., 2000, 2, 2085.
91%
Ph
SECTION 209: ALKENES FROM ALKENES 2%[ Rh(cod)Cl], 8% TPPDS
P
h
A
-
PhB(OII)?_, Na2C03 phase transfer agent , H 2 0
mPh 80%
Ph
TPPDS= p h ( P
Lautens.;Roy, A.; Fukuoka, K.; Fagnou, K.; Martin-Matute, B. J . Ain. Chent. Soc., 2001, 123, 5358.
'OBr PI1
, 140"C, NaOAc
\ /
Pd-NaY zeolite, DMAC
89% trum (<1% cis)
Diakovitch. L.; Koehler, K. J . Anz. Clionr. Soc., 2001, 123, 5990.
CO2Me Me02C 2.5%Pdz(dha)3dha, 1 d 10%PPh, , DMF, 23°C
Me02C
a'
63% COlMe Castaiio, A.M.; Mindez, M.; Ruano, M.; Eschavarren. A . M J. Org. Chent., 2001, 66, 589.
a
8
-..$
Et2211, 2% phosphoiwnde 1%~ CuBr , MQS , ether -40°C -+ -10"C, 18 h
+
Ph (47 : 53) quant Ph Ph Malda, H.; van Zijl, A.W.; Arnold, L.A.; Ferinca. B.1, Org. Lett., 2001, 3, 1169.
Section 209
453
Alkenes from Alkenes
1.
P h M q SiI, i
2.
,CUCN, TIIP ,-4o'C
),
,l'€IF, -78°C PhMezSi
f
0' P -,
72%
OPh OPh
3. NIi4Cl Liepins, V.; BBckvall. J.-E, Org. Ixtt., 2001, 3, 1x61.
-N
\
C12(PCy? h R u X I I P h
N 20°, 16h CH2C12 Ts 84% Kindennan, S.S.; V ~ I IMaarseveen, 1.11.; Schoemaker, H.E.; Hiemstra, 11.; Rutjes, F.P.J.T. Clrg. Lett., 2001, 3 , 2045.
I TS
I
Michelet, V.; Gallund, J.-C.; Chaiwuult, L.; Savignac, M.; GenCt, J.-P. Org. Lctt. 2001, 3, 2065.
88%
1. Gruhhs' catalyst DCM. reflux
2. KI: , HzO2 KIICO, , MeOM TI-IF
Ph Org. I x t t . , 2001, 3 , 2069
=-11P
Y
Ps
Ph'
WLndtr.; Barzilay. C.M.; Dyckman, A.J. J. Am. Chern. Soc., 2001, 123, 179. I
.
454
Compendium of Organic Synthetic Methods, Vol 11
Section 209
5 % Grubhs' c;itillyst e
[hmiin] PF6, 8 0 T , 1 h
I
I
Tos Tos van Vuuren, E.; Sterrenburg, J.G. Org. Lett., 2001, 3, 3785.
;-
0
QTPS
QTBS
5 % CI-I,=CI-IPh
0 . 3 M CHCI, 3% Gmhhs' catillyst
-
Ir
'%,,,A
@ \, \
60% (>95% E) wt.D.L.; Usher, L.C.; Estrella-Junenez, M. Org. Lctt., 2001, 3, 4275. b \,\-'
Ph-
E
\
5% Gruhbs'catalyst
Ph
Ph
Verhicky, C.A.; Zercher. C.K. Tc~truhdronLett., 2000, 41, 8723.
62%
J-OTBDMS
34
( :
)76%
1
[CpRu(NrCMe),+ PF6-
"'/-'.* ,b ; Surivet,
.I.-P.; Toste, F.D. J.
h i .
Chwi. Soc., 2001, 123, 2897.
5% 80"C,3h Mo catalyst *
/
Ph
/
93% ( 74% ee) Cefalo, D.R.; Kiely, A.F.; Wuchrer, M.; Jamieson, J.Y.; Schrock, R.R.; J. Am. Clzetii. Soc., 2001, 123, 3139.
Section 209
Alkenes from Alkenes
455
Bn
LhkuyLL; . I . Senzaki, M.; Kadoya, R.; Morimoto, T.; Miyake, N.; Iawa, M.;
J. Am. Chern. Soc., 2001, 123, 4607. QB 11
20% RuC&(PCy3)2=CIIPh
PhH, rt, 1 h
B nU
Ralner.;Cox, J.M.; Allwein,
QBn
Z H
B no
89%
S.P. Tctruhedron Ixtt., 2001, 42, 179.
78%
\
\ 0
'0
Yamamoto, Y.; Nakagai, Y.-i.; Ohkoshi, N.; Jtoh. K . J. Ain. Chern. Snc., 2001, 123, 6372. CII2=CIIC02Bu , 2 eq C S ~ C , ~ , PhBr
Yang,
2% I'd(OAcX, 4% IMesI-ICI DMF , 120"C, 1 h Synlett, 2001, 1539.
*
-co2Bu
97%
c.;rna
AlhCniz, A.C.; Espinet. P,; Martin-Ruiz, B.; Milstein. D. J . Am. Chcni. Soc., 2001, 123, 11504. (700 psi)
CH,=CII,
2 eq SnMe, ,45"C, cat TaC15
PhCl , autoclave , 4 h Andes, C.; Ifarkins, S.B.; Murtuza, S.; Oyler, K.; Sen. A. J. h i . Clierri. SOL-.,2001. 12.3, 7423.
*
C,H,C€I=CII,
94%
Coinpendiuin of Organic Synthetic Methods, Vol 11
456
J. Ariz. Cherti. SOC.,2001, 12.3, 6989.
Littke, A.F.;
a,dv.les.; Xiang, B.;
m
Section 209
N
TS
-
Kong, N.; Stafford, D.G. J. Am. Chem. Soc., 2001, 123, 7461.
Ts
I
(3
supercritical CO, ,4O"C Clz(PCy3)zRu=C€IPh
riirbtnLr.;Ackerinann, L.; Beck, K.; IIori, H.; Koch, D.; Langemann, K.; 4
.
B
W. J. h
i .
CIwii. Soc., 2001, 123, 9000.
93% Liehl, M.; Six, C.;
1. 5% Giuhbs' catalyst ,40"C 2.11, , 25°C t
El0 ZC
tandem inetathesis-hydrogenation Louie, J.; Bielawski, C.W.; h h h s J. Airr. Cltenz. SOC., 2001, 123, 11312.
d
OBZ
2 a1 CH,=CHCN ,CI1,ClZ
5% Ru carliene complex 45"C, 2 h
88% (4: 1z:E) Randl, S . ; Gessler, S.; Wakaiiiaatsu, H.; Blechert. S . Synlett, 2001, 430.
95%
457
Alkenes from Alkenes
Section 209
W
O
B
Z
5% RUcatalyst, CIIzc12 45"C, 12 h
z
NC
0B -Z
98% Randal, S . ; Buschmann, N.; Coiinon, S.J.; &&&-L ' Synlctt, 2001, 1547.
/cwn Br
, KZCO,, DMF
cat [PdC1(CJIS)I2 130°C , 20h teti-iphosphine ligand
COzBn quant
Feuerstein, M.; Doucet. & SuiteUiM, Synlett, 2001, 1980.
0
L
N
CO/II,(100 utm), toluene cat Kh,(CO)i,,
100°C
80%
Ph
Ph
Settamholo, R.; Caizzo, A.; LjlZZjn'oni. R . Totrulieron Lett., 2001, 42, 4045. Ph---I
mCN
CII,=€IICN , [ h ~ n i n ] P f j ~ /
Ph
NEt, , 100°C , 10% Pd/C
92%
ionic liquid medium
m; ., . . Shimizu, Y.; IIoshi, T.; Suzuki, T.; Ando, M.; Ohkuho, K.; Yokoyma, C. Tetruhedron I ~ t t . 2001, , 42, 4349.
C&(PCy,),Ru=CIIPh DCM , reflux , 3 h
Chandra, K.L.; Sxavanan, P.; Siiieh. V K. Tcrrulidron LAt., 2001, 42, 5309.
02
Me 1. t-BuIi ,TMCDA, 0°C hexune
2. Me1
=
83%
~
\ Si(i-Prh
Matsuzuno, M.; Fukuda, T.; Iwao. M. letruhedi-on Ltjtt., 2001, 42, 7621.
\
Si(i-Pr)3
458
Compendium of Organic Synthetic Methods, Vol 11
Section 209
Grela.;Bieniek, M. Tetruhedron Lctt., 2001, 42, 6425. COZR
R = (-)-8-phenylmenthyl
89% (8:l de) &g!hv, J.H.; Mnnn, L.W.; Myers, B.J. Tc,truhedrnn Lett., 2001, 42, 8773. PhBr , TBAB , NaHCO3
p h y m 2 B n 8 2 % JcozBn 130°C , Yd-benzthimle coiiiplex* Ph ionic inedium
m; Nacci, A.; Monopoli, A,; Lopez, L.; di Cosmo, A. Tetruheclron, 2001, 57, 6071.
BdSJYclirlh.; . .. . . Bnkthadoss,
M.; Reddy, G.J. Syntliesis, 2001, 919.
/'
Fang, X.; W ; l r B . P . ; Watkin, J.G. Synth. Cnininun., 2000, 30, 2669
OMC-N
Br
30
,,,#C 0 2 t - B ~
cat P ~ ( O A C,)dppe ~ AgzCO,, MeCN 85T,1 d
OIIC-N
Bhat, L.; Steinig, A.G.; Appelhe, R.; de M ~ ee. r9 .Eitr. J. Org. Chein., 2001, 1673.
54%
Section 209
Alkenes from Alkenes
Ph
-0Ts
I
459
Ph
, dioxane ,40"C, 1 d
I
I I
k
II
/
1 1 2 0 , NMP , W"C, 5 h
I
I10
\\
cat Pd(PPh3), ,NCOOII
+
DMF , 3 0 ° C , 12 h
II 0
1) 42% OH
1-10 Oh. C.&; Yoo, 11,s.; Jung, S.H. Chcin. Lett., 2001, 1288. HSiMe20SiMe3, 60°C
--P h &shlez0siMe3 0.3 RhI(PPh3)3 Cun. J. Chent., 2001, 79, 1522. Mori, A.; Takahisa, E.; Nishihara, Y.: Ph
S i Me,OS i Me 3
Jlilt. G.; de Mesnil, F.-X.; Luers, S. Angew. Cheiiz. Int. Ed., 20171, 40,387 Ph-I
CI-I2=CIICO,Gt, sonication , 2 h
h
Ph
C
O
Z
E
t
[hmim] Br , cat Pd(OAc)2 Deshmukh, R.K.; Rajagopal, R . ; a i n i v a s a n . K.V.Chcin. Conmun., ~ 0 0 1 1544. ,
87%
b”ol
Coinpendiuin of Organic Synthetic Methods, Vol 11
460
,bm s/
Section 209
Mez
MLi
Mo carbene coinplex
t
PhH , 5 inin 63% conversion Aeilts, S.L.; Cefalo, D.R.; Bonditatehus Jr., P.J.; IIouser, J.11.;
Angcw. Chem. Irit. Ed., 2001, 40, 1452.
/“ii */a OC0,Et
2.5% Pd2(dba)3dba, 1 d 10% PPh3, DMF, 23°C
CO2Me
Meo2C
2eqHz0
Md2C
C02Me Castaiio, A h { . ; Mtndez,
63%
M.; Ruano, M.; Echavanen.
A.M. J. Org. Chem., 2001, 66, 585.
OBU
Vallin, K.S.A.; Larhed, M.; Johansson, K.; JIallhere. A . J. Org. Chem., 2000, 65, 4537. 10% (2,6-MqC6II,O),Ti 25 74)CYC 1ohexylMgCI
THF , 0°C Okamoto, S.;
I
)
se.
-r,J , ~
-
rt , 1 d
~ 1 c 11.1~,11 soc., 1.
85%
2000, 122, 1223.
PhNIIz , AcOH , =flux, 5 h
-co2Me
Ph
66%
/ C O I M e Pd-Cu-inontinoiillonite KIO Waterlot, C.; Coutuiier, D.; Pieo. B. Tetruhcrlrnn Lett., 2000, 41, 317.
/Cd4 13
Gruhbs‘catalyst
DCM , 20°C , 20 h *C,H,, +GHi3 70% Ahined, M.; Arnauld, T.; Banett.n.C I.&; Braddock, D.C.; Plack, K.; Procopiou, P.A. Org. Lztt., 2000, 2, 551.
Section 209
461
Alkenes from Alkenes
Segorhe, M.M.; Atlrio, J.; w e t e r o . J.CTetruhedron Lett., 2000, 41, 1983
B zO(1-12C) 7 Chatterjee, A.K.; Morgan, J.P.; Scholl, M.;Gruhhs. R , E
J. Am. Chem. Soc., 2 0 0 0 , 122, 3783.
O r g . Lett., 2000, 2 , 663.
Warrington, J.M.; Yap, G.P.A.;
SiMe,?Ph C61113
L
1. I'hMe2SiCu, TIIF, -40°C 2.
&'-SG:,,
c r 1 3 y 7 5 %
, TIIF, -40°C
-
0 Liepins, V.; Karlstriim, A.S.E.; F l c k ~ 3 1 1 .J.-& Org. Lett., 2000, 2, 1237.
'$
DCE , 0.1 M ,it ,2 h 5% IRh(dppil)C1]2/ApSb~6
Cao, P.; Wang, B.; Z h 3 n g . J .
h i .
*
Clrertr. Soc., 2000, 122, 6490.
d8
0
462
Section 209
Compendium of Organic Synthetic Methods, Vol 11
A\
ph
SPh I
Cp2TUYOEthl2
Ph
THF
71%
phg +
Fujiwara, T.; Kato, Y . ;m e d a . T,Tetrahedron, 2000, 56, 4859. JSiMe3 ,N Me
3 eq PhCICII
EtO
*
TIIF, 55°C , 4 d G(CO).j
NMe, ph$NM'
EtO
Schirmer, ti.; Flynn. B.L.;
0 v. J.&
EtO (1.8 Tetrulierlron, 2000, 56, 4977.
1 ) 62%
Kondriltenko, M.A.; Fiedler, C. Org. Lett., 20U0, 2, 3917.
PhCgCH , cat CoBr,(dppe) cut Bu4NBH4, cat ZnI, 94%
DCM, rt
m;du Mesnil, F.-X. Tetruliulrori IA'tt., 2000, 41, 6757.
6
Ph
ethylene, [Ni(MeCN)6][BFd]2
Ph
*
Ph AlEt2C1, PPh,, 1 h 87% Fassina, V.; Ramminger, C.; Sefeciin, M.;Jvlonteiro. A .L. Tetrulzedron, 2000, 56, 7403.
Alkenes from Alkenes
Section 209
W
/
N
I'
Ts
463
-6
DCM ,0.1 M ,rt , 1 2 h
N /Ts
Oi-Pr C
PC?*
O
>99%
Ru:
la
PCY3
0
Angew. Cliern. Int. Ed., 2000, 39, 3896.
Schurer, S.C.;Gessler, S.; Buschmann, N.; Blechert. S.
Angew. Cheni. Int. E d , 2000, 39, 3898.
&
L.iOTf , MeCN, 6 h
*O
0
c
0
>99%
alternative to LiC10, 0 N. Synlert, 2000, 877.
AurC.;Gil, R.; Kalsey, S.; I,uhin-Gennain,
Bertozzi, F.; Olsson. R.; Frejd, T. Org. Lc.tt., 2000, 2, 1283. PhI, cat-I, DMF , 140"C, 2 h
4Ph
Ir
mPh
Ph cat--I = PdCI2 + P(OPh,),Br o n intercalated clay Varma.;Naicker, K.P.; Liesen, P.J. Tctruhc,dron Ixtt., ZYY9, 40, 2075
95%
Section 209
Coinpendiuin of Organic Synthetic Methods, Vol 11
464
Wrivht. D.L; Schulte 11, J.P.; Page, M.A. Org. Z ~ t t . 2000, , 2 , 1847.
uCchMe , Pd2(dha), , NEt, PhI
-
D- 100, MLCN
Ph*C4Me
89%
D-100= perfloriiattxl solvent - mainly n-perfhorooctane Moineau, J.; Pozzi, G.; Quici, S.; Sinou. D, Tetruherlron L t t . , 1999, 40, 7683.
do&
%A
PhI, Pd(OAc)2 , PPhi c 84% superaitical C 0 2 , 75-85°C Ph 1600 psi er. C . N Tetrulzedron Lett., 1999, 40, 2221. Shezad, N.; Oakes, R.S.; Clifford, A.A.; OMe
OSiEt,
0
OSiEt3
10% C ~ ~ ( P C Y ~ ) ~ R U = C I I P ~ CH2C12,reflux
=
87%
Edwards, S.D.; Lewis, T.; Tavlor. R.J.K. Tetruherlron Lett., 1999, 40, 4267.
0
30% CI2(PCy;)3Ru=CIIPh
--.
CHzClz, 50°C
Pdauette.L.A.:M&ndez-Andino, J. Tetruhadron Lett., 1999, 40, 4301. PhCl , 1.5% Pdz(dba),
JCoZMe 6 % P(t-Bu), , 1 . 1 eqCsZCO3 * Ph diiunine , 100"C, 42 h A.F.: Ey. G.C. J. Org. Cliertr., 1999, 64,10.
6S% C02Me 76%
Section 200
Alkenes from Alkenes
465
(Me4-Phen)OPd(Me)C1 , DCE
*
NaBAr4 , 2 5 " C , 5 miri Ar = 3,SC,H,(CF3L
WldenhncfLr.;Vodehra, A. Tetruliedron Lett., 1999, 40, 8499. 1
Me 86% (2:l isomer ratio)
1
TBDMSO v s
i
M
%
e- , 1M LiCIO, "DMm&
MeOII/TIIF
*
2,6111tidine CH(0Meh
OMe Frey, D.A.; Reddy, S.H.K.; Moeller.
83% J. Org. Chena., 1999, 64, 2805.
t - ~ u 1% RhCI(PPh3)3
toluene , 0.1 M
t
reflux
P A ; Glorius, F.; IIusfeld, C.O.; Iaigkopf, E.; I m e , J.A. J. Am. Cherit. SOC., 1999. 121, 5348.
96%
'I
2 eq PhCII=CH, ,5% Mo catalyst Phrr , 2 2 0 ,~A r + * hP
S7% (>98% truns, 96% ee) La, f).S.; Ford, J G.; Slatately, E.S.; Bonitatebus, P.J.; Schrock, K.R.;IIoveyda, A.II. J. Am. Cheni. Soc.. I Y Y Y , 121, 11603.
c7=
-0.4~
5% Grubhs' catalya II xcH -A ?c
Chatterjee, A.K.; Gruhhs.
Org. Lett., I Y Y Y , I, 1751.
60% (2.3: 1 E:Z)
4
Compendium of Organic Synthetic Methods, VoI 11
466
OMe
Section 209
; : 2 ; ~ ~ ; : ! % ; * ~C02Et 8%
in ionic liquid
Carmichael, A.J.; Org. Lett., 1999, 1, 997.
MeO
. Holhrey, J.D.; McCorinac, P.B.; Seddon, K.R.
0
OBr 5Lx1
, Na2CO3
Cat Pdz(dha)3dbd4 K y 3
99% (9223 of other isomers) Hartung, C.G.; Kiihler, K.; Beller, M. Org. Lett., 1999, 1, 709.
Widenhoefer.; Perch, N.S. Org. Zxtt., 1999, 1, 1103.
LC,,
PhH, henzoquinone , AcOH Ph-Co2Et
* 10% Pd( O A C ),~t-B uOOH Ph sealed tube, A q O , 9 0 T Jia, C.; Lu, W.; Kitamura, T.; Fuiiwara. Y , O r g . b i t . , Z999, 1, 2097.
72%
PhI,Pd/C,NEt,,8O0C,2d A C 0 2 M e
z
P h-C02Me supercritical C 0 2 , 100 bar Qcchi. S.; Fahrizi, G.; Gaspanhi, F.; Villani, C. Synlett, 1999, 345.
PhI Leese, M.P.;
, NEt,, toluene, 100°C 4Cc)2Me * 1% [I’d catalyst frum guanidinium phosphine supported on glass heads] , 16 h . . I SyriIctt, 1999, 1645.
65%
mco2M
Ph
87%
Section 209
Alkenes from Alkenes
467
SPh I
3 Cp2Ti[P(OEt)31, THF,12h
*
71%
Ph Fujiwara, T.; Takeda. T. Synlcrf, I Y Y Y , 354. 2 eq
M
Ph
mh
-
PI-,
5% Gruhhs' catalyd
hPPh 82% (4:lE:Z)
Synletr, 1YY9, 557.
Blanco, O.M.;
2.5% [p-cyine~ne)RuCl~]~, 5.5% PCy,
*
DCM
; Ackemiann,
(),
82%
L. Chonr. Corninun., 1999, 95.
REVIEWS: "Kecent Chemistry Of Benzocyclohutenes," Mehta.
G;Kotha, S. Tefrdedron, 2001, 57, 625.
"The Transannular Diels-Alder Strategy: Application To Total Synthesis," Musault, D.; Tor6, A.; Now&, P.; Tr.rruhedron, 2001, 57, 4243. "The Preparation Of Mono-, 1, 1-Di, Trails-1, 2-Di- And Trisuhstituted Ethylenes By . .; Toader, D. Synlett, 2001, 458. Benzotriazole Methodology," "Diels-Alder Reaction On Solid Supports," Yli-Kauhaluoma. .I, Tetrulzedron, 2001, 57,7053. "Advances In The Heck Chemistry Of Aryl Bromides And Chlorides," Whitcomhe, N.J.; Hii, K.K.; mison. S.E, Tetruhedron, 2001, 57,1440. "Cycloadditions IJnder Microwave hradiation Conditions; Methods And Applications," De La Hoz. A.; Moreno, A.; Lang. F. Eiir. J. Org. Cheni., 2000, 3659.
A; Diaz-Ortis,
"Recent Advances In Lewis Acid-Catalyzed Diels-Alder Reactions In Aqueous Media," FrinPuelli. 0.;Pizzo, F.; Vaccaro, L. E m J. Org. CIicni., Z U O I , 439.
E; Piermatti,
468
Compendium of Organic Synthetic Methods, Vol 11
Section 210
"Formation Of Cumulenes, Triple-Bonded, And Related Coinpounds By Flash Vacuum Pyrolysis Of Five-Membered Iieterocycles," Yranzo, (3.1.; Elguero, .I.; Flammang, R.; Eur. J. Org. Chetn., 2001, 2200. "Synthesis Of Heterocycles Using The Intramolecular Heck Reaction Involving A 'formal' AntiEl Bialy, S.A.A.; Yakura, T. Heterocycles, 1999, 51, 1957. Elimination Process," Ikeda.;
SECTION 210:
ALKENES FROM MISCELLANEOUS COMPOUNDS
PhCH=N-NIITs
B(OMeh, t-BuOLi , THF
*
reflux, 6 h
G.W.; Wu, Z.; Ju, Y . Tetrulwdron Lett., 2001, 42, 4759.
PhCH=CHPh 82% (4852 trans:cis)
Ph2P=CHC02Me, PhC02H A&O,=9 Si02=xH 2 0 , toluene I~flUX
*
*azMe
Chowdhury, M.A.; Senlwku, €I.; Tokudda. M.; Masuda, Y.; Chiba, T. Tetruhedron LEtt., 2001, 42, 7075.
0sit-B uMe2 Ph Kakiya, H.; Shinokuho, H.;
2.2 eq Bu3MnLi ,TIIF
82%
*
58%
Ph
Tetruhedron, 2001, 57, 10063.
1. LDA , THF -55°C 0 \S
2 . 2 q M s C l , DCM, r t
I
Ph
Satoh.;Hanaki, N.; Yamada, N.; Asano, T. Tetrahedron, 2000, 56, 6223.
-
92~76%
469
Alkenes from Misc.
Section 210
- -
NHBoc
3 . 6 q DBIJ, 2 q EtNO,
BocIIN
CO,Et
Nagano, T.; finoshita.
I-L Bull.
l M F , -40°C
rt
En&
C h i n . SOC. Jpn., 2000, 73, 1605.
BulSnH, AIBN
PhII, heat Ph
Lrtt., 1999,I, 873.
78% (97:3 Z E )
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 15 PREPARATION OF OXIDES This chapter contains reactions that prepare the oxides of nitrogen, sulfur and selenium. Included are N-oxides, nitroso and nitro compounds, nitrile oxides, sulfoxides, selenoxides and sulfones. Oxunes are considered to he amines and appear in those sections. Preparation of sulfonic acid derivatives u e found in Chapter Two and the preparation of sulfonate esters in Chapter Ten.
SECTION 211: OXIDES FROM ALKYNES 0
II
1. Cpgr(H)Cl 2. MezZn
B y =
,PPh2
71%
3.CHZIz 4. P hCI I=N- P( 0 ) Ph2
85:15
:p
Wipf. P,; Kendall, C . Org. Lett., 2001, 3, 2773.
Bu
2. 1. Cp2zl(II)cI Me2Zn
B y =
3.
0
h
L
-
1
B
u
$i"
11% 4
II PhIIGN- P- Plp
74% 0
hp'
Ph'
CI-IzC12,reflux Wipf. P.; Kendall, C.; Stephenson, C.R.J. J. Am. Chenl. SOC., 2001, 123, 5122.
SECTION 212: OXIDES FROM ACID DERIVATIVES PhS03H
Nafion-1%.PhN ,reflux , 2 0 h
u, Mathew, T.; Ph.SO,CI
'
-
PhSOZPh
48%
Chenr. Cornnzitn., 2001, 1696.
BnBr , SmRIgClz ,THF
50°C , 2.5 h Zhang, J.; Zhang, Y. J . Cherir. Res. (S), 2001, 516.
+
PhSO,Bn
75%
Section 214
Oxidcs froin Aldehydes
1. m
B
S0,Cl
r ,AlC13-Fe H20,4h
2. 2M IICl Saikia, P.; Laskar, D.D.; Prajapati, D.;
+3-
so,c 1
. ,
471
+P
+
85%
m..I S , Chenz. Lett., 2001, 512.
PhII , Zn , 7 0 sec miavwaves
* +rn2Ph 72%
Kasture, S.P. Synrh. Corimrtn., 2UUU, 31, 1065.
SECTION 213: OXIDES FROM ALCOHOLS AND THIOLS NaN02-AcOII-IIC1, 6 b Phcri201r Buuah, A,; Kalita, B.; bus. N.C.. Syrtlctt, 2000, 1064.
*
PhCII2NO2
85%
miavw ave s A.D,; Shinde, N.A.; Bandgar, B.P. Org, Prep. Proceed. Int., 2000, 32, 269. 1. MeLi , THF ,-78"C
Phsrr 2.-7X"C ,
Sandrinelli, F.;
..
t
0, Phl.lllf- N, S02Ph
PhS02Me
75%
3. workup H 4. Me1 , cat Bu4NBr, H20/toluene acetone, 85"C, 1 d Beslin, P. Orx. Lttt. ZYY9, I, 1177.
SECTION 214: OXIDES FROM ALDEHYDES
PhCHO
i-PrN02 , 3 eq Zn , 0°C
*
Ph
+(-
61% H i-Pr Gautheron-Chapoulaud, V.; Pandya, S.U.; Cividino, P.; Masson, G.; Py, S.; VallBe, Y. Synletr, 2uuz, 128 1. AcOH ,EtOI-i,2 d
412
SECTION 215:
Compendiuin of Organic Synthetic Methods, Vol 11
Section 215
OXIDES FROM ALKYLS, METHYLENES AND ARYLS
NO;? zeolite, , 0 3 , MeCN 70°C
.r
@02N*No2
Peng, X.;SuzukifJl Org. Lett. 2001, 3 , 34331.
NO2
85%
/
12%
61%
Karade.;Kate, S.S.;Adude, R.N. Synlett, 2001, 1573.
Bak, R.R.; SJnallrldtw. A.J. Tctruherlron Lett., 2001. 42, 6161. Montrnorillonite KSF Bi(N03)
‘ITIF, 10 min Samajdar, S.; Becker, F.F.;
7’etruherlron Lett., 2000, 41, 8017.
OcaRo. &; Bruzana, E.; I~5pez-GonzBlez,D.; Jidnez-Estrada. M. Org. Prep. Proceed. Int., 1999,31, 117.
Oxides froin Amities
Section 217
473
SECTION 216: OXIDES FROM AMIDES
I1 BOCH
F3kz
F3C
N
C02Me
V
, CH2CIz
5 h ,-20°C
+
0°C
Detomaso, A.; Cursi. K. Tetruhedron Lett., 2001, 42, 755
-
OI I
I
COzMe B ~ ~ / ~ \ / 82%
SECTION 217: OXIDES FROM AMINES PhIO , inontinorillonit K10 MtCN , 30 min, rt
Ph,P Mielniczak, G.; Eopusiriski, A. Synlett, 2001, 505.
+
Ph3P=0
96%
2-butanone , t-BuOOII, 80°C + Ph3P=0 94% Ph,P+BI 13 Uziel, J.; Darcel, C.; Moulin, D.; Bauduin, C.; Jue&. S. Tetruherlrnn Asymm., 2001, 12, 1441. PhNII,
I120z ,Me011 , 3 0 m i n
--
PhNoz
98%
[Ti(Oi-Pr)p , SO%)14202] Dewkar, G.K.; Mikalje, M.D.; Ali, IS.; Paraskar, A S . ; Jagtap, H.; Angew. Chenz. hit. Ed., 2001, 40,405. Me 2N 1.1
NaNO, , wet SiO,, DCM, rt
+ MezN-NO quant Mg(I-ISO,), , 1 h ZolflL.ol.; Chaemi, E.; Madrakian, E.; Kiany-Borazjani, M. Synth. Cornmun., 2000, 30, 2057. With KIISO5 on wet silica gel. Zolfieol. M A ;Bagherzadeh, M.; Chaghamarani, A.G.; Keypour, 11.; Salchzadeh, S . Synth. Cornmun., 2001, 31, 1161.
generate HOF in situ
/ aq MeCN , -20°C * OZN Disk, S.M.; Mickelson, E.T.; IIenderson, J.C.; Tour, J.M. Org. Lett., 2000, 2 , 3405. we*I-I~o, , HC0,II rt,4h Balicki, K.;Goliiiski, J. Synth. Corrirnun., 2000, 30, 1529.
i
-
90%
474
Coxnpendium of Organic Synthetic Methods, Vol 11
6N A Ph
ph
I
Section 219
PhA ;--
(salen)Mn(III) complex
I 0-
Ph 81%
*o
UHP , MeOH ,0°C OH Cicchi, S . ; Cardona, F.; Brlmdi, A.; Corsi, M.; C&~.JLTetruhedron Lett., 1999, 40, 1989.
5% xjNaClO , 3 h
N
1
OH Cicchi, S.; Corsi, M.; pph3
J. Org. Chcnt., 2999, 64,7243.
0 2
t O=PPh, qumt aOrg. k t t . , 1999, 1, 583.
,Me,CCH,CHO, DCE
A
FsQ , S O T , 3 h
Wanr.; Zhnng,
70%
,Me
14.; Song, G.; Lu, X. Synth. Cornnzun., 1999, 29, 11.
NaN02, CzHzO4.2 HZ0 , DCM
EtZNH
68%
0-
NzO (140 bar) , 100°C. 3 h
Poh, S.; €Iernandez, R.; Inagaki, M.; Lesson. P
n
+'i"
0°C + lt
h
it , 2 h
EtzN-NO
95%
Synth. Cornnrun., 1999, 29, 905.
SECTION 218: OXIDES FROM ESTERS NO ADDITIONAL EXAMPLES
SECTION 219:
Bn-S-B n
OXIDES FROM ETHERS, EPOXIDES AND THIOETHERS 15% (CLCl(tpp), I-IZOZ, EtOH
B nSO,-B n
Ir
lt
Marques, A.; Marin, M.; Buassc. M.-F, J. 01-8.Chern., 2001, 66, 7588. Bu/s\Bu
3% 11202. Me(CglI17)3N HSO4
10% Na2W04, PhC03H 50°C , 1 h Sato, K.; Hyodo, M.; Aoki, M.; Zheng, X.-Q.;
*
$O \
'
Bu
quant
95%
'Bu
Tetruhedron, 2001, 57, 2469.
Section 219
Oxides from Ethers
475
78% (96% ee) Saito, B.; Katsuk i.T, Tetruhedron Lett., 2001, 42, 3873.
(CF~CO)zO/I-IzOz C0,Et 0. V G - ; Gavryushin,
75% A.E.; Balenkova, E.S. Tctruherlron Lett., 2001, 42, 4397. 0
Fe(NO3)3-FeBr3 , MtCN PhHS,Me
C0,Et
MeCN
II
t
air, 25°C
PhHs\Me
92%
Martin, S.E.; Rossi, L.I. Tetruhedron Lett., 2001, 42, 7147.
MB-Bentonite composite , 2 h
L-
BuNS\ Bu
0
It Bu/s\Bu
'Oz ,0.005 M .. IIahlht; Tangestaninejad, S.; Mirkhani, V.; Yadollahi, B. Tetruhedron,
S
Me'
Ti(Oi-Pr)4,R-BINOL , 1 d 1120, toluene , 0°C ' Massa, A,; Lattanzi, A,; Siniscalchi, F.R.; silica acetate/NzO,,
quant
2001, 57, 8333.
67% (80% ee)
*
Tctruherlron Asymm., 2001, 12, 2775. 0
DCM
II
Ph/ S \ P h
rt , 5 inin * PhHS\Ph Firouzahatli. H.: Iranpoor. N.; IIeydari, R. Synth. Cornn?un.,200Z, 31, 2037.
97%
0
horseradkh peroxidase t
II
77% ee Ph Ozaki. S.-i.; Watannhe, S.; Hayasaka, S.; Konuma, M. Cheni. Conzmun., 2001, 1654. Ph/"
Me
0 2
hexamethylene trianune-Brz ,rt Et
0
II
CI-IC13-N20,< 2 inin * E t / S b ShJdh,lni.; . Teimouri, M.B.; Safaei, H.R. Synth. Conrnrun., 2000, 30, 265. 7
< .
91%
476
Compendium of Organic Synthetic Methods, Vol 11
xj
PhNS\
0
IIIO3, steam bath ,301nin
PhHs,
Shirini, F.; Zolfigol, M.A.; Lakouraj, M.M.; Azadhar, M.R. Russ. J. Org. Chent., 2001, 37, 1340.
-
M q S i Q , K 4 , MeCN Me
-15"C, 5 h Chen.;Huang, Y.-P. Tcrruhedrori LEtt., 2000, 41, 5233.
~
'~ 'c1 p
, D' C Ml , r t
Bu/'\Bu
. J.: KO-
C2Z"24
.
AS--Me
5h
Syntlz. Coniniitn., 2000, 30, 979.
II
*
Ph
PhHs,
Section 219
Ph
93%
Ph/%e
-
92%
0
II
/s\ Bu
Bu
95 %
0
II
NaI04, TBAB , M t O H
88%
1d * C22Hz4/S\Me YaJnauloto. T.; IIayakawa, T.; Yoshino, M.; IIata, Si.; Hirayama, Y. Org. Prep. Pmcsecl. Int., 2000, 32, 192. IT,
0.5 PhIOz , toluene/HzO 2 eq MeOPh t a t a t e 20% CTAB ,rt
quant ,53% ee s Tohma, H.; Takizawa, S.; Watanahe, H.; Fukuoka, Y.; Maegawa, T.; I(ita. J. Org. Cherri., I Y Y Y , 64,3519. Mi102 , cat H2SO4 ,SiOz PhHS,Me
0 b
II
PhHS\Me 40°C. 1 h Abhasi, M. Synth. Coniinim., 1999, 129, 1485.
;-
B U-S-B
. .
Balicki.
a
u
urea-H,02 , F A A , MeCN
rt,2h Synth. Conitnun., I Y Y Y , 29, 2235.
Bu-SOZ-BU
80%
95%
Section 221
Oxides from Hydrides
477
SECTION 220: OXIDES FROM HALIDES AND SULFONATES
PqOEt), ,A1,03 micmw aves , 10 min
Ph-Cl
Ph-p//O
~
/ \OEt
85%
El0 Kaboudin.; Balakrishna, M.S. Synth. Conintun., 2001, 31, 2773.
PhCIIO , Ni(dppe)Br2/Zn THF ,75"C 91%
Kun. S . ; Yoon, J.-Y.; Lim, C.J. Synlett, 2000, 1 1 5 1 .
SECTION 221: OXIDES FROM HYDRIDES
NO2 ,O, , DCM -1 ooc
Nose, M.;
.
F
NO2 -
(23
77)
76%
; Suzuki, 11. J. Org. Chent., 2001, 66, 4356.
IINO? , CHCI, , 3 h (NII &S 0,-NiS04-6 H 2 0
85% purdl5% ortho Tasneem, Ali M.M.; Paianiia. K.C.; Saiparakash, P.K. Synth. Coniniun., 2001, 31, 1123.
F ZalflgoL;Baghertadeh, M.; Madrakian, E.; Ghaemi, E.; Taqian-Nasah, A. J. Chern. Rex (S). 2001, 140.
478
Coinpeiidiuin of Organic Synthetic Methods, Vol 11
0
N-hydroxyphthalimide ,6O"C IINO, , PhCF, , 15 h
Section 221
ON'' 56%
Isozaki, S.; Nishiwaki, Y.; Sakaguchi, S.;
0
Chein. Conitnun., 2001, 1352.
NO2 ,cat N-hydroxyphthalimnide air, 70"C, 14 h
Sakaguchi, S.; Nishiwaki, Y.; Kitamnura, T.; Jshii. Y. Angew. Chenr. Int. Ed., 2002, 40, 222.
aoMe OTs
SiO2, A1Cl3-ZnCl2
iniuuwaves , 8 min
-F.M.; . . Dakanin, M.G. Tetruliedl-on k t t . , 2000, 41, 3479.
Ts
92%
ON02 ,Ti011
[eini~n](OTf) einim = lethyl-3-mne thyliinidilzolium
Laali.; Gettwert, V.J. .I.
95% (67.1:37.9 o:p)
Org. Chem., 2001, 66, 35.
8610 (77:23 3,44iMe:2,3-diMe) Mrlrquik. J.; Laporteiie, A.; Duhac. J.: Roques, N.; Desuturs, J.-R. J. Orb'. Clieni., 2001, 66, 421. c1
Me 1. Pd catalyst 2. M%Al coinplex 3. XIHCl ,90°C , PhI-I
Blum.;Berlin, 0.;
fL Syntliesis,
2000, 571.
; Ben-David,
Y.; Wassennann, B.C.; Schutte, S.; Schumann.
479
Oxides from Hychides
Section 221
10% Yb(0Tfh , HNO,
DCM ,reflux , 1d
F
F
92%
Bamtt. A.G .K; Braddock, D.C.; Ducray, R.;McKinnell, R.M.; Waller, F.J. Synlett, 2 0 0 0 , 57.
PhLSOzCl,solid state , 6 h Fe+3-moti tmoiilloni te ; Chowdari, N.S.; Kantam,
84% (o:rn:p ,5:095) M.L. J . Clzern. SOC.,Perkin Truns. 1, 2000, 2689
2 HNO3, A%O , 2 h TFAA , I-IP-zolite
0
s; Gihbins, T.; Millar, R.W.; Clardige, K.P.
J. Chem. Soc., Perkin Truns. I, 2UU0, 2753.
OH
C ~ I I ~ O , ~ ~ I IDCM ,O,
*
wet S O , , N a N 0 2 , 30 min
q
-
89% (+ 6.4% of 2,6-)
NO2
e0: 35:65 o:p
-Lolfieol.; . Ghaemi, E.; Madrakian, E. Synfh. Conzrnitn., 2000, 30, 1689. 2
N 2 0 4 , 0 2 , DCE cat z w l i t e H p , 1 d *
N -O2 85% (53:2:45 o:rn:p)
Smith.;Almeer, S.; Black, S.J. Cheni. Corrurzun., 2000, 1571.
0~~
OMe
CX"\ISi02 ,rt
DCM
* M
\ o/
e
~
OMe Grenier, J.-L.; Ciitteau, J.-P.; !J>telle. P, Syrrth. Cormnun., ZYYY, 2Y, 1201.
o
88% m
Compendium of Organic Synthetic Methods, Vol 11
480
2eq PhH
-
SOCl2, TfOM, 1 d
0
II
PhHS\
Olah.;Marina, E.R.;
Section 224
Synlett, 1999, 1397.
92%
Ph
EtOAc ,rcflux 82% NO+-lXciuwn-6 NO2 W N 4 12 Irannoor. N. : Firouzahadi. 1-1.; Heydari, R. Synrh. Crunnrun.,I Y 9 Y , 29, 3295. N 0, 70%)€12SOdSi02,H N 0 3
E M , 2S"C, 1 d
78%
Smith, A.C.; Narvaez, L.D.; Akins, B.G.; Langford, M.M.; Gary, T.; Geisleer, V.J.;
Synrh. Conimun., I 9 9 Y , 2Y, 4187.
AcONOZ-Clay
-cues.
FEt \ /
96% (44153 o:p) J.A.E;; Filho, A.P.O.; Moran, P.J.S. Synth. Conrnaun., 1999, 29, 2169.
*
SECTION 222: OXIDES FROM KETONES NO ADDITIONAL EXAMPLES
SECTION 223: OXIDES FROM NITRILES NO ADDITIONAL EXAMPLES
SECTION 224: OXIDES FROM ALKENES
v C 6 F I l 3
Nd-12P02,MeOH, r t
0
*
H,II
BEt, , 2 h Na 0/-'C,jH13 DeprGle, S.; Montchainn. J.-L. J. Org. Chnt., 2001, 66, 6745.
80%
Section 225
48 1
Oxides from M i x .
ENO, , Amherlyst A
-C02Me
inicmwaves , 7 inin
COzMe
..
Bdlllnl.; Bosica, G.; Fiorini, D. Tetruhedron Lett., 2001, 42, 8471.
SECTION 225:
85%
OXIDES FROM MISCELLANEOUS COMPOUNDS
IISllllllll ..
0
D’
2. 1. EtMgX n-decylMgX , TIIF,THF ,-30°C
0
II
Dsy;;l c
0-inenhyl
Br
Br
89% (>98%ee ,S)
Capozzi, M.A.M.; Cardellicchio, C.; Naso. F.; Spina, (3.; Tortorella, P. J. Org. Chem., 2001, 66, 5933.
PPh, ,DEAD PhI-I, rt , 2 h
c
0 1I
82%
MJL; Weiler, L. Oq.Lc,lt., 2001. 3, 643. 0
0
PhNH3-
II
P-
I’hI, 2% Pd(PPh3)4
I-I,
3 “1 NEt3 , MtCN
JVlontchamp. J.-I,.; Dumond, Y.R. J. Aiii.
\ /
CIwiii.
II
* Ph-
P- 0- NH3+ ‘H
Soc., 2001, 123, 510.
L’M
e
0
-
9
~
10%)In(OTf), , 120°C
88% (38:62 0 : p ) Frost. C.G.; IIartley, J.P.; Whittle, A.J. Synlett, 2 U U Z , 830.
97%
482
Coinpendiuin of Organic Synthetic Methods, Vol 11
M 2.4KeqNBr, ,2% , 3H20 0 min OS03- PyrH'
p
Section 225
h
A
t
41%
A g N 0 3 , 0°C
Steinrnann, J.E.; Phillips, J.11.; Sanders, W.J.; 0
II
Org. LRtt., 2001, 3. 3557. 0
1. BBr3 , toluene-hexane
I
-30°C-
II
-70°C
Et / p\ 0 E t 2.MeOH, 20°C OEt Synthesis, 2001, 553. Gaovry, N.; 0
11/
95%
Et+oI1 OH 0
II
-P\
0 C 31-17
Ph$+ BF4-, DMF
*
ph/
II
P-OC3H7
a t Pd(PPh3)4 , KzC03 90"C, 3 h Zhou, T.; Chen. %.-C. Synth. Coniinun., 2001, 31, 3289. 0
c,I-17
0
!
\
0
SOCl2, DCM b
/sSms -78°Crt Ph
Schwan., Strickler, R.R.;
98%
OGH7
!
90%
Dunn-Dufault, R.; Brillon, D. Eur. J. Org. Chem., 2001, 1643.
NH4N03 , TFAA , MtCN PhB( Olih PhNO2 78% Salzhrunn, S.; Simon, J.; Surva P m s h . Q . K ... PLtrlsis. > . . N.A... Olrlh. * Q.kSynlett, 2000, 1485. R
PhMgBr , 5 h
Cardellicchio, C.; Fracchiolla, G.; Naso.; Tortorella, P.; Holody, W.; -hie Tetruhedron I z t t . , 1999, 40, 5773. n
Guzman, A.; Alfaro, R.; Diaz, E. Synth. Conzrnun., 1999, 29, 2967.
:w'
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
CHAPTER 16 PREPARATION OF DIFUNCTIONAL COMPOUNDS
-
SECTION 300: ALKYNE ALKYNE
Ph
=
TIPS
6 CU(OAC), TBAF,4h ) P h P yle ther
= =
Ph
68% Hueft, M.A.; Collins, S.K,; Yap, G.P.A.; Fallis, A.G. Org. Lett., 2001, 3, 2883.
Dai. W.-M; Wu, A. Tetrahedron Lett., 2001, 42, 81 %HI7
-
CuClz, KF/AlZ0, rniaowaves , 2 min
-
c8rI,, -
Kahalka. G.W.; Wang, L.; Pagni, R.M. Synlett, 2001, 108.
CpJr
3
-
C,H, 7
61%
1. CUCl
2. Bn-Br
,~ O O C 6 h,
Bn Liu, Y.; Xi, C.; Hara, R.; Nakajima, K.; Yamazaki, A.; Kotora, M.; J. Org. Chetn., 2000, 65, 6951.
-
36%
Compendium of Organic Synthetic Methods, Vol 11
484
=
Ph
SiMe,
C u a ,DMF ,60°C
-
Section 301
= =
Ph 6h Nishihara, Y.; Ikegashira, K.; Hirahayashi, K.; Ando, J.-i.; Mori.;Hiyama, T. J. Org. Chem., 2000, 65, 1780. 2.5% Pd2(dhah , 15% TFP 20% CuI, 2.5 eq TEA
P
h
T
B Br
'
* P h DMF , 8 0 T
Ph >99%
= =
Ph
71%
TFP = trk- (2-fury1)phosphine
&m. W,; Thomas, S.A. Org. Lett., 2000, 2, 2857. Si(i-Pr)3 BuLi ,hexane -78°C- 4 0 ° C B( r
70%
(i-Pr),Si Si( CPr), Eisler, S.; Tykwinski, R.R. J. Am. Chem. SOC., 2000, 122, 10736. CuC12, NaOAc, 3 h
-L-
P
supercritical C 0 2 Xi, J.;
P
P
h
quant
Chem. Commun., ZY99, 2369.
REVIEWS: "Acetylenic Coupling: A Powerful Tool In Molecular Construction," Siemsen, P.; Livingston, R.C.; Diederich. F. Angcw. Chem. Int. Ed., 2000, 3Y, 2632.
SECTION 301: ALKYNE - ACID DERIVATIVES
Koster, F.; Dinhus, E.; Duiiach, E. Eur. J. Org. Chem., 200Z, 2507
Section 302
485
Alkyne - Alcohol
yS”B::pc€40 -$
SECTION 302: ALKYNE - ALCOHOL, THIOL
TMS
TMS +$e
ML
OMe
TMS
(97 Savall, B.M.; Powell, N.A.; Boush. W.R. Org. Lett., 2001, 3, 3057.
, toluene, 60°C
TMs()-+
‘’W
22% Ho
3) 96%
= + , 5 0 % NEt,
OTMS
N Me2
20% Zn(0Tfh , 5 h
77% (98-%ee)
Anand, N.K.; Carreira.E.M. J . Am. Chem. Soc., 2001, 123, 9687.
Et02C--CI I 0
1. Me’s> Me
C=CII,
p --
w t Sc complex 2. KZCO,, EtOII
95% (98% ee)
Cvanb.; . . . Sweeney, Z.K.; Kovis. T.; Tedron, J.S. J. Am. Chem. SOC., 2001, 123, 12095. 1. CpzTiClz ,Mg ,TIIT; 2. PhCHO 3 . 1 0 % €ICI Yang, F.; &o.
G .: D
U Tetruhederon k t t . , 2001, 42, 2839.
72%
PhC-CII , ZnMez, toluene
CHO
10%chirdl amino-alcohol
Lu, G.; Li, X.; Zhou, Z.; k. W.L.. C t
,
b A S .C Tetrahedron Asyrnm., 2001, 12, 2147.
486
Compendium of Organic Synthetic Methods, Vol 11
Section 302
re-LGADH ( a reductase)
Schubert, T.; Hummel, W.; Kula, M.-R.;
x
92% ee Eur, J. Org. Chem., 2001, 4181.
HCCH , toluene ,Zn(OTf), N-Meephedrine , i-PrzNEt , 7 d* 79(:8%e)
CHO
Sasaki, H.; Boyall, D.; Carreira.
E.& Helv.Chim. Actu, 2001, 84, 964.
acetone , t-BuOK , 2 0 min
P h =
solvent free amoto. H,; Yasaka, S.; Tanaka, K. Bull. Chent. Soc. Jpn., 2001, 74, 185. P h O C H ,toluene, 23°C Zn(0Tf)L , NEt,, 2 h
I-PKHO
-iP&
(+)-N-methylephedrine
95% (90% ee) J. Am. Chem. SOC.,2000, 122, 1806. Frantz, D.E.; Flssler, R.;m e i r a . E .M,
Ph
2" alcohol dehydrogenase from Therinunueobucter ethanolicus Iieiss, C.; M l i ps. R.S, J. Chem. Sor., Perkin Trans. 1, 2000, 2821.
30% (60% ee, S)
, toluene, 23°C
H O( - =
(-)-N-methylephedrine , NEt, Zn(OTf)L Boyall, D.; L6pez, F.; Sasaki, H.; Frantz, D.;
C,H,7
-
1
5-nonanone , 4 eq SmI,
Org. Lett., 2000, 2, 4233.
*
c,H,~+.OH
BU
THF 84% Bu . . Kunlshlma.;Nakata, D.; Tanaka, S.; Hioki, K.; Tani, S. Tetruhedron, 2000, 56, 9927.
487
Alkyne - Aldehyde
Section 303
PhCmCLi , toluene, 1% M q G a -78°C ,0.1 h
BnO
Ooi, T.; Morikawa, J.; Ichikawa, H.; Maruoka.
BnO
P h G C H ,&Me2, 10%chiral amino alchol
PhCHO
90%
y Tefrclhedron Lerr., 1999,40, 5881.
toluene/TIIF , -20°C
* F% ,H -) ph
Nb 70% (68% ee, S)
u; Upadhyay, V.; Decamp, A.E.; DiMichele, L.; Reider, P.J. Synthesis, Z999, 1457. S d z , Pd(PPh,), , TIW
9
*
87%
Bn Bn Aurrecoechea. J.N; Fafianjs, R.; Arrate, M.; Gorgojo, J.M.; Aurrekoetxea, N. . I . Org. Chent., 1999,44, 1893.
1. (CyhB€I ,O"C + rt
*
62%
2.MeOH, 1 h
C3<-H ,7
Yu,S.; Li, N.-S.;
GEI7
u. G.W. J. Org. Chetn., I9Y9,44, 5822.
Tzalis, D.; Knochel. P. Angew. Chetn. Inf. Ed., 1999,38, 1463.
-
SECTION 303: ALKYNE ALDEHYDE
ci21125
=
CI1,OH
'I'iCb/NEtl, CHZC12 0°C , 1 h
* Ci2H25
€Ian, Z.P.; Shinokuho, 11.; Oshlma.K.ynletf, 2001, 1421.
-
CHO
90%
Compendium of Organic Synthetic Methods, Vol 11
488
Section 305
-
SECTION 304: ALKYNE AMIDE Bu
\
N-CHO
/
Ts
Bu
1. PPh3 , CC14 ,TIIF ,60"C
\
7
c
2. BuLi , THF ,-78°C
+
-30°C
/
Ts
99~86%
B n i c k n e r . y n l e t t , 2000, 1402.
1. B uLi , toluene ,0°C
BnNHTs
2. Ph(OTf)-I-C&H Witulski. B,; Gopmann, M. Synlett, 2000, 1793.
*
BnN(Ts)-C-C€I
90%
REVIEWS: "Recent Advances in the Chemistry of Ynamines and Ynamides," Zificsak, C.A.; Mulder, J.A.;
IJsunr.;Rameshkumar, C.; Wei, L.-L. Tetruhedron, 2001, 57, 7575. SECTION 305: ALKYNE - AMINE SiMe3-
Ph//N-Bn
Fischer, C.;
GI117
5% [Ircm(cod)]i THF, 23°C , 1 d
Ph
SiMg 76%
Org. Lett., 2001, 3, 4319.
-
Bn2NH, (CIIOX, ,microwaves
*
CuI A 1 2 0 3
C&€I17
=
Sahalka. G.W.; Wang, L.; Pagni, R.M. Synlett, 2001, 676.
-
O\"Bn
XII
GH11
MqSiCSCH , l o % Zn(0Tf)z 25% i-Pr,NEt, CHIC& 2S"C, 12 h
CHzNBnz
90%
9
<
"7 ,Bn *
C5H1 1
Frantz, D.E.; Flssler, R.; Carreira. E .M. J. Ain. Chem. Soc., 1999, 121, 11245.
2% SiMq
Section 306
:)I[
Alkyne
- Ester
489
-)I[
/& -196°CHC=CH , THF 23°C
\
Me
/M" 93%
\
M"
R.;
k h a g d L U ; Calahrese, J.C.; Davidson, F.; Diasa, H.V.R.; Goerlich, J.R.; Krafczyk, Marshall, W.J.; Tamn, M.; Schmutzler, R. Helv. Chim.Acta, 1999, 82, 2348.
REVIEWS:
u; Rameshkumar, C.; Wei, L.-L. Tetruhedron, 2001, 57, 7575.
"Recent Advances in the Chemistry of Ynamines and Ynamides," Zificsak, C.A.; Mulder, J.A.;
SECTION 306: ALKYNE - ESTER CO, MeOH , PdBr,, 2 h
P h =
c
Ph
CuBr, , 2 eq NJICO, Li, J.; Jiane.;Chen, M. Syntlz. Comnzun.,2001, 31, 199.
=
COzMe
80%
2% Pd( OAc), , S O T
2.6% phosphinooxazoline ligand toluene
Lucking, U.;
;.\I-
[
1
t-Bu
Synlett, 2000, 1261.
(83
t-Bu
+j], 17) 90%
10% [Ar(t-Bu)N]3MoCl bluene ,80°C
M
.
e
0 p Mathes, o q C.; Lehmann, C.W.2J. Ant. Chem. Snc., 1999, 121, 9453. 0
91%
w
Section 308
Compendium of Organic Synthetic Methods, Vol 11
490
BuOZCCI, DCM 2.2% Pd(OACk-PPh:,
=
=
89% w Ph COZBU 1,2,2,6,6-pentamethylpiperkline 4ilimethylaminopyridine Bottcher, A.; Becker, H.; Brunner, M.; Preiss, T.; H e n k e w; De Bakker, C.; Gleiter, R. J. Chcrn. SOC., Perkin Trans. 1, 1999, 3555.
-
SECTION 307: ALKYNE ETHER, EPOXIDE, THIOETHER 10%Tic14 , MeOH ,rt 95%
hP~->Ph " Ph Mahrwald.; Quint, S . Tetruhedrnn, 2000, 56, 7463.
-
1. COZ(CO)8 , cH*c12 ,rt /OH
2' HO*CSH,l
C5H11
70%
3. BF,*OEt,, -20°C 4. CAN , acetone, 0°C Diaz, D.D.; Martin. V.S. Tetruhedron Lett., 2000, 41, 9993.
Oxone, H 2 0 , MeCN-DMM KzCO3, AcOH , 3 h Wang, Z.-X.; Cao, G.-A.; Shi. Y . J . Org. Chern., 1999, 64, 7646.
6
SECTION 308: ALKYNE - HALIDE
/
NMe,
1. PPh,, CHI3, f-BuOK
~
2. t-BuOK, -78°C
mhel. P.: Rossat. 4Tetruhedrnn Lelt., 1999, 40, 8579.
6
-
I
/ 80~80% NMe,
-
Alkyne - Ketone
Section 309
49 1
e- ,NaI ,MeOH
w
C
p
h
=
x
88%
. . Nlshleuchi.;Kanahe, 0.;Itoh, K.; Maekawa, H. Synlett, 2000, 89. Br
II
CuI,MeCN, 1 d
*
40°C
11
+
Ph
- -
Ph
28%
SECTION 309: ALKYNE - KETONE
C3H7
=
TBHP , 0 2 ,70"C, 1 d
C3H7
CUCl2*2 H 2 0
U;Fong, W.M.; Chao, L.C.F.; Fung, S.1I.C.; Williams, I.D.
0
74%
J. Org. Chem., 2001, 66, 4087.
p h Y / OH
[Cp+RuCl( acetone ,pzMekRuCp*Cl] N H p 4 * ph$
78%
rellux, 4h 0
Cp*=NsCcjM~j Nishihayashi, Y.; Wakiji, I.; Ishii, Y . ; J. Am. Chem. SOC., 2001, 123, 3393.
I
1 . 4 eq t-BuLi ,-78°C 2 . C 0 , - 7 8 " C , 1h
I
3 . 2 tq PhCIIzBr, 1 h -78°C rt
. .
*
+
Song, Q.; Hen, J.; Jin, X.; XLZ; J. Am. Clieni. SOC., 2001, 123, 10419.
65%
-
Section 309
Compendium of Organic Synthetic Methods, Vol 11
492
=
Ph
()-SeCOMe cu
* <-hP
DMF ,80°C
84%
. Synlett, 2001, 1571.
Qian, H.; Shao, L.-X.;
1,
-
,m/MZ03
Pi1
P h -
(*- - i f 91% cat Pd(PPh,)zClz-CuI, NEt, Ph microwaves , 4 niin m e . J.-x.; Wei, B.; Huang, D.; Hu, Y.; Bai, L. Synth. Conmzun., 2001, 31, 3337. Wei, B.; Hu, Y.; Liu, Z.; Fu, Y. Synth. with CuI/NEt3, microwaves. See Commun., 2001, 31, 3527; .I. -X,Wei, B.; Hu, Y.; Liu, Z.; Kang, L. J. Chem. Res. (S},2001, 146.
u;
3eq
CgH17CIC-H
0
0.05 [RuCh(p-cymenel~ C8€l,7 0.2 pyrrolidine , PhH 6O"C, 12 h
gB-c6
Na, Y.; Choi, E.; Kim, S. Org. Lett., 2001, 3 , 2089.
;-
1.
*
PI1
Ph
DCM ,BF3.OE t2 2. "I NH4Cl
Ph
88% (86% ee) Shen, L.; Taylor, N.J. J. Am. Chem. Soc., 2000, 122, 1822.
;M . . J-
PhzSh
=
BzCl, D C M , heat, 3 h
Ph
* 3% Bd'dCl(PPh3)z
)-..
Ph
82% Kakusawa, N.; Yamaguchi, K.; Kurita.; Tsuchiya, T. Tetrahedron Lett., 2000, 41, 4143.
Section 3 11
-
Chowdhury, C.;
493
Allcyne - Alkene
Tol-COCl , 5% CUI
+
\
NEt, ,r t , 30 h
83%
. Tetruhedron, 1999, 55, 7011.
0-
Sun, A.-M.;
To1
80%
Tetruhedron, 1999, 55, 13201.
SECTION 310: ALKYNE - NITRILE NO ADDITIONAL EXAMPLES
SECTION 311: ALKYNE - ALKENE
5%JPd( PPh3)A , 40°C
65%
Radhakrishnan, U.; Stantz. P.J. Org. L c q 2001, 3, 859.
I
TS
Bu-GC-Ag , 0.5 Pd(PPh,), /
Dillinger, S.; Bertus, P.; Pale. P.
or&Lett., 2001, 3, 1661.
5% [(Z-allyl)PdCl]~, NHEt, 10% TDMPP, TIIF,rt , 2h
* P
Rubina, M.; Gevorgvan. V. J. A I ~ Clzeiit. . Soc., 2001, 123, 11107.
h
y 70%
P
h
Section 3 11
Compendium of Organic Synthetic Methods, Vol 11
494
SPh
,cat PdC12(PPh3)2 Bu
O H /-=
CuI , THF ,i-Pr2NH , 4 h
0Ts
u Emmerich, ; D.J.; Silveira, C.C.; Martins, T.L.C.; Rodngues, O.E.D. Synlett, 200Z, 369.
OH
n m
Ph
Te
Ph
,MeOH/NEt,
10% PdCl,xJuI, 6 h
-
85% Moro, A.V.; Braga, A.L.; Silveira, C.C.; Stefani, H.A.
;-
OH
Synlett, 2001, 1473.
* t - B u G - B u Me,Si-Bu 10% e Pd(PPh3)4,21 h 20% AgI ,DIPEA B U& F.3 H2O Bertus, P.; Halbes, U.; pale. P, Eur. J . Org. Chem., 200Z, 4391. ~
uOTf
B
=
Ph
1. 1.5%€IgCl~ 2. BuLi , -78°C
Me
-
3. ZnBr,. -78°C rt 4.5% Pi(PPh,), I 0°C , 1 h Ma-S,; Zhang, A.; Yu,Y.; Xia, W. J. Org. Chern., 2000, 6S,2287.
Wco2E1
Et
(-u B
OAc
C5H,]3 eq ZnCh , 210% eq i-Pr2NEt -.IF, 5% Pd(PPh3)4, CUI
L
0.025M. NFIjBF4, MeOH ,60"C cat thiolate-bridged dimthenium catalyst
(CH2ho
Nishibayashi, Y.; Yamanashi, M.; Wakiji, I.; Angew. Chem. Int. Ed., 2000, 3Y7 2905.
60%
y-+E
67°C. 4 h (YII 1 Condon-Gueumot. S.; Linstrumelle, G. Tetrulzerfrnn, 2000, 56, 1851.
/=
87%
74%
3
(CI M
I0
69%
Section 313
495
Acid -Alcohol
1.20%PdClz ,20%CUI, MeOH , Ph-TeBu Zeni, G.;
2. NEt, , 4 h , C~HI=-,
GHI1
,seto. J.V, Tetruhedron Lett., 1999, 40, 4619.
XO GH17
-
T
BuhI+Ph
OTf
2% PdClz(PPh3h , K2cO3 2 NEt, , DMF ,3O"C, 3 h
CElHl7
Pirguliyev, N.Sh.; Brel.;Zefirov, N.S.; Stang, P.J. Tetruhedron, 1999, 55, 12377.
REVIEWS: "Cycloaromatization of Open and Masked 1.3-I-Iexadiene-S-ynes- Mechanistic and Synthetic Aspects," * Eur. J. Org. Chem., 2001, 457.
SECTION 312: CARBOXYLIC ACID - CARBOXYLIC ACID
A
C02, e- ,0.1 M Et4NC104, DMF
Ph
Senboku.; Komatsu, 11.; Fujimura, Y.;
'
.--
Synlett, 2001, 418.
. .
C
0
2
H
66%
CCOZH CO,II
RuC13/HI05 ,H 2 0 , CC14
lrif fith.
L IIOZC
MeCN ,rt * W.P.; Shoair, A.G.; Suriaatmaja, M. Synfh. Coniriiun., 2000, 30, 3091.
86%
SECTION 313: CARBOXYLIC ACID - ALCOHOL, THIOL
A
Ph
1. AD-mix
2. 0.25 2TEMPO, 0.02 NaOCl NaOCI,
*
PhH zC x: quant x 60% (>98% ee) Aladm, F.J.; Guerra, F.M.; Moreno-Dorado, F.J.; Bustamante, J.M.; Jorge, Z.D.; Massanet. W Tetruhedron Lett., 2000, 41, 3200.
496
Section 3 15
Compendium of Organic Synthetic Methods, Vol 11
CO/N2D2 (200/800/100 psi) THF , H 2 0 , Pd-C ,CuCI,
-CO2€I
18 h
OH
(22% 24%) 59% conversion Shen, C.; Garcia-Zayas, E.A.; Sen. A. J. Am. Chent. SOC.,2000, 122, 4029. 1 . 2 q L D A , THF, -78°C 2. L i , 5% DIBB , t-BuCHO , -78°C
*
C1-C02H
t-Bu Pastro, I.M.;
COzH
52%
Tctrulzedron Lett., 2000, 41, 5335.
-
SECTION 314: CARBOXYLIC ACID ALDEHYDE N O ADDITIONAL EXAMPLES
SECTION 315: CARBOXYLIC ACID - AMIDE
iiL
t- Bu / \ N
1.
Ph
Borg, G.; Chino, M.;
toluene ,0°C 2. cat RuCb=H20,N d 0 4 CH2C12, M&N/I-120
*
t-BU/s\N
O2
Illman. J . A , Tetruhedrnn Lett., 2001, 42,
0
x
Me *Ph H
CQZH
8 0 ~ 6 2 %(99: 1 dr) 1433.
60 eq co , 120°C , PdK:
I
N - m thylpyrmlidine 98% L B r , 1% If,SO, 11 * acetainide Beller. M.; Moradi, W.A.; Eckert, M.; Neumann, 11. Tctrulzedron Lett., 1999, 40, 4523.
CHO
MeCN
1. HZSO4, € 1 2 0
M :1-0e
2. M e 0 0.25% PdBr2/2 PPh3
Beller.;Eckert, M.; Moratli, W.A. Synbtt, 1999, 108.
/ \
76%
Section 317
Acid - Ester
497
-
SECTION 316: CARBOXYLIC ACID AMINE
#
-0
Buillus meguteriuni PYR 2910 KHCO3 ,N H ~ O A C1, h
CO,H N K phosphate buffer (pH 7) H suprcritical CO, 59% MJtsuda.; . . Ohaishi, Y.; Harada, T.; Yanagihxa, R.; Nagasawa, T.; Nakmura, K. Chern. Conunun., 2 0 0 1 , 2194. N
Ir
KEVIE WS: "Recent Developments in Catalytic Asymmetric Strecker-Type Reactions," Angew. Chem. In?. Ed., 2001, 40, 875. Related Methods:
Section 315 (Carhoxylic Acid - h i d e ) . Section 344 ( h i d e - Ester). Section 351 (Anine - Ester).
SECTION 317: CARROXYLIC ACID - ESTER 1 . aq NaOH , TIIF , 0°C
70%
2. IIBO+ J. Org. Cheni., 2000, 65,5834.
4:
(DIIQI))zAQN, Me011 , ether
0
Chen, Y.; l i a n , S.-K.;
I1O2c(CI I 3 C 0 , I I
99% (95% ee)
J . Am. Chern. Soc., 2000, 122, 9542.
€ICOzBu+ctme, D O W ~50WX2 X i
70"C, 3 h
;-
. . '
I
.
aCOzMe
-30°C
I IO,rA CH d,CO,B u
95% Ishii, Y.; Fujisaki, S. J. Clieni. SOC., Pcrkin Truns. 1, 1999, 3023
Section 322
Compendium of Organic Synthetic Methods, Vol 11
498
CARBOXYLIC ACID - ETHER, EPOXIDE, THIOETHER
SECTION 318:
NO ADDITIONAL EXAMPLES
SECTION 319: CARBOXYLIC ACID - HALIDE, SULFONATE NO ADDITIONAL EXAMPLES
-
SECTION 320: CARBOXYLIC ACID KETONE Cu(OAck-H20, air, 90°C Ph
3% aq AcOH:MeOH
NO2
Nikalje, M.D.; Ali, I..; Dewkar, G.K.;
.
61%
phC ' 02H
Tetruhedron L.ett., 2000, 41, 959.
Also via: Section 360 (Ketone - Ester).
SECTION 321: CARBOXYLIC ACID - NITRILE NO ADDITIONAL EXAMPLES Also via: Section 361 (Nitrile - Ester).
-
SECTION 322: CARBOXYLIC ACID ALKENE OTMS
1. PhCIIO
Me$i
dOTMS
2. NHdCI Lensen, N.; Mouelhi, S.;
P hCHO
, DMF , KOH, rt 96% Synth. Coniniun., 200Z, 31, 1007.
CH2(C02112,Bentonite microwaves, 5 min
=
phL(m2H 79%
Loupy, A.; Song, S.-.I.; Sohn, S.-M.; Lee, Y.-M.; &von. T.W, J. Chem. Soc., Pcrkin Truns, 1, 200Z, 1220.
m2H
Section 322
1.
499
H2N*~d N H ,rt , 5 h
2. Ph(h4e)CIBr 3. H30'
Me
-
Acid - Alkene
62% (57:43 RR:RS)
Brun, E.M.; Gil, S.; Parra. M, Tetruhedron A.synzrii., 2001, 12, 915.
1.1 atmCO, 2 DMU Ni(cod)z ,TIIF, 0°C
" \
2 . 2 eq PhZnCl 2h , 0°C
Takimoto, M.; Shimizu, K.; MmJl. PhCHO
B
'
Org. Lett., 200Z, 3, 3345.
~
69%~
Ph
CHz(COzH), , S O , , 4 min
83%
t PhCH=C HC02H mimwaves Kamar.;Reddy, B.V.S.; Reddy, P.T.; Srinivas, D.; Yadav, J.S. Org. Prep. Proceed. Int. 2000, 32, 81.
89% Zhu, S.; Pardi, S.;
0 Tetmhedron Lett., 2000, 41, 9589. EtZnBr , 5 % PdCl,( MeCN)L
*
/Iccog
I DMF ,25"C, 12 h Ct Aharhri, M.; Parvain, .I.-L.; Kitamura, M.; Noyori, R.; Duchsne, A. J. Org. Chein., 2000, 65, 7475.
90%
1. ClCH=CHCl , hv 2. 25% Z n , toluene 85~80%
3. A c ~ O 85°C , 0
Gauvry, N.; Coinoy, C.; Lescop, C.; Iluet. F, Synthesis, 1999, 574. CHz(COZH), , piperidine
0
* PhCH=CHCO,H quant micmw aves , 15 sec P e l l h , R.F.; Mamposo, T.; Gonzrilez, E.; Calderh, 0. Synth. Coinmun., 2000, 30, 3769. PhCI 1 0
~
Coinpendium of Organic Synthetic Methods, Vol 11
500
P h =
1 atm C@ ,Ni(cod),
t
2 eqDBU, 0°C
US.; Nakagawa, S.; Koizumi, T.; Hirayama, K.; -to.
J. Org. Chem., 1999, 64, 3975.
32% aq MeC03H
&OH
AcOII ,0°C , 3 d
Section 323
1 0
85%
ZH
Y,
H
H o 2 b 0 2 H
+
(5
2) 70%
e. A.B. Synth. Conznzun., 1999, 29, 1463.
PhCHO
CHZ(CO2II), , Py/Pip , 2 min
* PhCII=CHCO,H inimwaves De, A.; Karchaudhuri, N. Synth. Conrntcm., ZYY9, 29, 573.
97%
u; Also via:
Section 313 (Alcohol - Carboxylic Acids). Section 349 (Amide - Alkene). Section 362 (Ester - Alkene). Section 376 (Nitrile - Alkene).
SECTION 323: ALCOHOL, THIOL - ALCOHOL, THIOL ASYMMETRIC DIOLS
/a/
I . 5% microencapsulated OsO, 5% (DHQD)zPIIAL, 30°C
Ph
-
H \LMe
Ph+
Hb/
K3Fe(CN)6,aq acetone, K 2 C 4 2. K,Fe(CN)6, K2C03,2OoC
OH
HO
85% (78% ee) ibhavashi. S,; Ishida, T.; Akiyama, R. Org. Lett., 2001, 3, 2649.
&Ph Ph
1 . 5 H 2 0 2 , 2 q TEAA 2% O s 0 4 , 5 % flavin
(DHQD)zPHAL ,0°C r-BuOHIH,O
Jonsson, S.Y.;
Adolfsson.H.; Biickvall,
Lr
$P,h
Ph
OH
89% (90%ee) J.-E. Org. Lett., 2001, 3, 3463.
Alcohol - Alcohol
Section 323
J==
501
BnSePh, K 2 0 ~ 0 2 ( 0 H ) 4 KzCO3 , (DHQD)$'HAI-, iy t-BuOII , 1 d
Me
( y l : ph
Krief.; Castillo-Colaux, C. Synlett, 2001, 501.
-
RR-oli gomer-salen catalyst H,O ,MeCN/DCM ,THF NMP ,100"C
96% (97% ee)
98% (94%ee)
"O,,
J. Ant. Chem. Soc., 2U01, 1 2 3 , 2719.
Ready, J.M.;
Mehltretter, G.M.; DGhler, C.; Sundermeier, U.; &&,rJ&
Tctruhedron Lett., 2000, 41, 8083.
60% (>20:1 dr; >99% ee)
Notz, W.; J.ist. B, J. Am. Chcm. Sor., 2000, 122, 7386. KzOs02(OIl)4 , (DHQD)zPHAL
PhSe(O)Bn, KZCO, ,
p>
t-BuOOII*
%
-'t7 011
Knef.;Colaux-Castillo, C. Tetruhedron Lett., l Y Y Y , 40, 4189.
K6.
Ph
cat Ru(chiral his lunine)
DMF,HCOOII/NEt3 1 d ,30-60"C
z
96%(97%ee)
qPh OH
Ph
OH quant (90.4:9.6d1:nwso) 9 9 % ee , RR Murata, K.; Okano, K.; Miyagi, M.: Iwane, I*.; Noyori, R.; Ikariya, T. Org. Lett., 1999, 1, 1119. 0
Section 323
Compendium of Organic Synthetic Methods, Vol 11
502
NON-ASYMMETRIC DIOLS
PhCHO
3 eq S m , 2 M HCYTHF
20T, 1d
% +
Ph 80% (4852 dl-meso)
01I
Talukdar, S.; Fano .I.-J.& 01-g. Chem., 2001, 66, 330.
lltiit~t
CpzTi(Ph)CI ,Zn ,Me3SiC1
THF (0.05M) ,rt
*
O
O
OH
H
60% (99: 1 b-ms:cis) Yamamoto, Y.; Hattori, R.; Miwa, T.; Nakagai, Y.-i.; Kuhota, T.; Yamamoto, C.; Okamoto, Y.; I&&, J. Org. Chem., 2001, 66, 3865.
Barrero.;Cuerva, J.M.; Herrador, M.M.; Valdivia, M.V. J. Org. Chem., 2001, 66, 4074. Ph
ph-cIm
,TtIF
*
1% Zn-linked BINOL ,-30°C
OH 94%
Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Org. b t t . , 2001, 3, 1539.
0.1%K 2 0 a 4 , Cinchona alkaloid in ordered inorganic support
W C O Z f i
Ph
Motorina, I.;
K,Fe(CN), , K2C03 ,t-BuOWH20
.
Org. L.ett., 2001, 3, 2325.
(89 : 1 syn:antQ 9 2 % ~89%ee
j j C o +
Ph
OH
54% conversion
503
Alcohol - Alcohol
Section 323
p
10%Ti complex 3 eq Mn , 2 5 T
PhCHO
.-
15 eqTMS CI MeCN
&Ph
Ph
--6H
94%(96:4 d1:meso)
Bensari, A,; Renaud, J.-L.;Riant. 0, Org. k t t . , 2001, 3, 3863.
Bu
cat 0 ~ 0 4a, t NMM 2% TEAA
Jonsson, S.Y.; FZrnegCdh, K.; lhddlJ& -
PhCHO
~
catflavin
Bu+
B~
95%
OH J . Ant. Chern. Snc., 2001, 123, 1365.
1.3%Ce(Oi-Pr), , Mn TMSCl
-
2 . 2 N HCl 0 1I
CJroth.U.;Jeske, M. Synlett, 2001,
(80
129.
chiral Ru complex , HC0,H NEt3, CI12C12, S O T , 6 h 0
o<
Ph
+
OH 20) 96%
J +::j
H~IIIIIIII
HO
Ph
(58
83% a2 cossV.;Eustache, F.; Dalko, P.I. Tetrahedron Lett., 20111, 42, 500.5.
42) 79%
76) 90% Bartoll.;Bosco, M.; Marcantoni, E.; Massaccesi, M.; Rinaldi, S.; Samhri, L. Eur. J. Org. Chenz., 2001, 4670. (24
:
Ph
504
Compendium of Organic Synthetic Methods, Vol 11
Section 323
j+
a04 , K,fi(CN),, K2C03
mph
polymer-hound DHQD-PHAL
Ph
~
Ph
t-BuO€I ,H20,O"C , 1 X h
92% (99% ee) Kuang, Q,-Q.; WE. S.-Y.; Wei, L.-L. Tetruherlrnn L,ett., 2001, 42, 5925.
#
OH
CeC13.7 H,O-(COOH),
* H
MeCN , 2 11
O 98%
Xiao, X.; Bai. D. Synlt.fr, 2001, 535.
TiBr2/Cu ,DCM , 6 h
PhCHO
Lc o g t
.-
p r
PI,$
Ph
t-BuCN , -27°C
OH
OH
(96
4) -95%
Mukaivama.; Yoshimura, N.; Igarashi, K.; Kagayama, A. Tetruhedron, 2001, 57, 2495.
Me 0
Ph
2. TiC1, , DCM ,-30°C
Me
3. MeMgCl, THF, -78°C HO 4. H30+ (93
Bartoli.;Bosco, M.; Di Maartino, E.; Marcantoni, E.; Sambri, L.
7) 88%
Eur. J. Org. Chem., 2001, 2901.
OMe I
~ . _
Yauda,
M.;Okamoto, K.; Sako, T.; Baha. A . Client. Coirmun., 2001, 157.
Section 323
Alcohol - Alcohol
*
1. S m , TMSCl
PhCHO
505
h +
Ph
2. NH4CI
Yu, M.;
87% 0 1I
Org. Prep. Proceed. Int.. 2001, 33, 187.
1
TiC4:Zn , t-BuCN , DCE, 0°C
'
Ph
PhQ
P
h
OH
94% (71:29 dknzeso) Kagayama, A,; Igarashi, K.; Mukaiyama, T. Cun. J. Chein., 2000, 78,657.
HO
x-) 0
, 2.4eq BEt3
cat Ni(aca+, TIIF,rt , 1 d
Kimura, M.; Erne, A.; Tanaka, S.; ph\
d(cH2)40H
63% Angew. Clteiit. Int. Ed.,2001,40,3600.
/Ph
QH t-BuOOH, KH , DMF
OH
OH
78%
Liu, D.; b . S .A. Angew. Chern. Int. Ed.,2001, 40,4757.
PhCHO
cat In(&, Mg , Th4.XI TIIF, 2 h
Mori, K.; Ohtaka, S.; -Bull.
1 ,
'u.
Ph
67% (68:32 d1:mso) OH Chenz. Soc. Jpn., 2001, 74,1497.
6H Uekmatshoar. R.; Yavari, I.; Beheshtiha, Y.S.; Heravi, M.M. Monat. Chem., 2001, 132, 689.
506
Compendium of Organic Synthetic Methods, Vol 11
PhCHO , In1 ,DMI
+
Pd(PPh3)4, rt , 5 h
Section 323
i.'
Ph
HO 62% (22:78 .yn:unti)
33% (29:71 E:Z)
Araki.;Kameda, K.; Tanaka, J.; Hirnshita, T.; Yamanura, H.; Kawai, M. J. Org. Chem., 2001, 66, 7919.
CeC1397 H2O-(COOI-I), 2h
OH
Xiao, X.; Bai. D. Synlett, 2001, 535.
98%
m a k i . Y.; Yamada, T.; Tanaka, N. Synlett, 2UO1, 1311.
1. nc4 2.0.1 Py 87% (97:3 syn:anti) Bartnli. G,; Bosco, M.; Bellucci, M.C.; Dalpozzo, R.; Marcantoni, E.; Sambri, L. Org. Lett., 2000, 2, 45.
0SiMqI-I
CHO
cat TBAF ,TIIF, -78°C
Miura, K.; Nakagawa, T.; Suda, S.;
'
HO Ph (96 Cl?em. I*.tt., 2000, 150.
Ph
4) 87%
Section 323
Alcohol - Alcohol
507
UP
1. Li , 5 % DTBB ,TI-IF, -78°C 2. t-BuCIIO, -78°C + -20°C
C O -lPh
* GBu
3. PhCHO ,-78°C 4. €120 ,-78°C 20°C +
~ o u h e l o .F,; Saleh, S.A.; Yus.
PhCHZOH
4
AlIFeF2
J. Org. Cheni., 2000, 65, 3478.
PhCHO
Al/LiF , 5 d
H2O
68%
'uPh
Ph
~
HZO
OH 76% (1.l:l meso:dl) I i , L.-H.;
Org. Lett., 2000, 2 , 1129.
69% (58:42 dknleso) Ghatak, A.; Becker, F.F.; W k . B .& Tetrulwrlron Lett., 2000, 41, 3793.
Li, T.; Cui, W.; Liu, J.; Zhao, J.;
Chc.rn. Coritnzi~n.,2000, 139.
S d z , MLQWTIIF, 0°C , 12 h t
qm Ph
95% (99: 1 ann':syn)
Keck. CLE, Wager, C.A. 01-8. Lett., 2000, 2 , 2307.
2
PhClIO
1.5 Tic& , 2.2 B U ~ N I DCM/hexane , -78°C
--+
rt
~
Ph
99% (93:7 dkmeso)
OH
Tsuritani, T.; Ito, S.; Shinokuho, H.; Qshima, K. J. Org. Clzenz., 2000, 65, 5066.
508
Section 323
Compendium of Organic Synthetic Methods, Vol 11
XI,,ECN
PhCHO
Hayakawa, R.; w
u
0
Phq
P
. M . Chem. Lett., 2000, 724.
h 90% (>99:1 d1:niaro)
OH
+ 8 eq HMPA
91 <1 <1 98 Miller, R.S.; Sealy, J.M.; Shahangi, M.; Kuhiman, M.L.; Fuchs, J.R.; Flowers 11. R.A. J. Am. Chem. SOC., 2000, 122, 7718. CHO
+ 8 eq LiBr
T
i
C
l
2
;
,
*
p
&
a
/
c1
Enders.;Ulltich,
y
59% (73:27 d:meso)
E.C. Tetruhedron Asymm., 2000, 11, 3861.
1. L i , DTAB , TIIF, -78°C 2. t-BuCHO, 20°C
c 1-on
3. PhCHO ,-78°C
* I- BLI€% -
4. H,O
68%
Fouhelo, F.; Yus. M. Tetrahedron Lett., 1999, 40,743.
ph-YPh
LiAIH, ,O2
;-
,
..
0 MBximo, N.;
- PhYYph OH
OH I ; R h i l a , A. Tetruhedron Lett., 1999,40,6427.
Yh-Me3SiC1, THF 6 7 T , 20 h
Ph Bu Ph Bu Qgawa. A.; Takeuchi, 11.; Hirao. T, Tctruliedron LEtt., 1999, 40,71 13.
90%
66% (85:15 d k m e ~ o )
Section 323
509
Alcohol - Alcohol
2.2 eq Ni(cod), ,DMF t
3 h , r t + 60°C
Ar
Ar = 3,4-di(OC&,,)C&,
97%
T J . Org. Clieiri., 1999,64,655.
Reisch, H.A.; Enkelmann, V.;
OH OH
1% OsO, ,mcpha
*
N-methylmorpholine
.:j;-i
Bu Bergstad, K.; Piet, J.J.N.; Bkkvall, J.-E. J . Org. Ch~nz.,1999,64,2545.
2
Ph (i-P10hTiBH4, CH2C12
I ~Olllllllll
-20"C, 5 min
HO
HO
Ph Ph (100 0) 95% Ravikumar, K.S.;Sinha, S . ; Chandrasekaran. S. J. Org. Chern., 1999,64,5841. Ph
. , F.ernandez-Mateos.; de la Nava, E.M.; Coca, G.P.; Silvo, A.R.; Gonziilez, R.R. Org. Lett., 1999, 1, 607.
1. C ~ H- 3 I
3
Sihf/le2a
NEt, 2. TiCh , toluene, -78°C Fujita, K.; Inoue, A.; Shinokuho, H.;
*+
O
OH Org. Lcrr., 1999,1, 917.
32~69%
510
Compendium of Organic Synthetic Methods, Vol 11
Section 324
1. i-PrCHO, lS%LiOi-Pr, ether, rt 2. NaOH , MeOH
Ph
Mascarenhas, C.M.; Duffey, M.O.; Liu, S.-Y.;J
74% (96:4 dr)
3% CpZTi(Ph)Cl, Z n , Me3SiCI
*
THF, rt
Yamamoto,
ooH
y Org. lett., 1999, 1, 1427.
y
"#' ##
OH
40% (99:1 trunsxis)
Y.;Hattori, R.;
Chern. Conimun., 1999,825.
PH OH
70% (90 10 &meso)
Hirao.;Hatano, B.; Imamoto, Y.;Ogawa, A. .I. Org. Chwi., 1999,64, 7665. REVIEWS: "Synthesis and Chemistry of Dithiols,"
Also via:
T
; Sayed, S.H. Synthesis, 2002, 1747.
Section 327 (Alcohol - Ester). Section 357 (Ester - Ester).
SECTION 324: ALCOHOL, THIOL - ALDEHYDE
1.2
Me2SCHCI" SO3CF3-
2eq DBU,THF
-
c
2 . 3 eq Bu4NOH , toluene 100°C OMe &to. K.-i.; Sekiguchi, T.; Akai, S. Tetruhedron Lett., 2001, 42, 3625.
quant
OMe
Section 325
51 1
Alcohol - Amide
OH PhCHO ,2.5 Ti(OBu)4
C3HcHzCHO
t-BuOK, TIIF ,0"C 97% (57:43 dr) Tetraherlron Lett.. 2000, 41, 4415.
Han, Z.; Yorimitsu, H.; Shinokuho, 11.;
*A
Section 330 (Alcohol - Ketone).
Related Methods:
SECTION 325: ALCOHOL, THIOL - AMIDE
,,,,,\+"
5% Pd(PPh,)h, I d , i-PrCI-I0
P h 7 N I 7//i ME
'IIIF-HMPA , HZO, rt
Ph
NIIMTSOH MTS = 2,4,6-@imr:thylphenylsulfonyl Ohno, H.; Hamaguchi, H.; Tonaka. T. J. Org. C h m . , 2001, 66, 1867. OS02N MQ
I
62%
OH
AlCI, , 140°C
*
Ih Benson, G.A.;
; Shelly, D.P.; &&ne.W.J.
Tetruherlron Lett., 2001, 42, 8729.
BnNH2-Dihal , TI-IF rt , 30inin
b~ P.-0.; Zheng, X.; Dcng, X.-M.
N HB n 0
98%
Tetrulzerlron Lett., 2001, 42, 9039.
NBn2 1. LDA , THF ,-78°C 2. I-PCHO ,-78°C
Se
i-Pr (94 Murai, T.; Suzuki, A.; &&.& J. Chmz. SOC., Perkin Truns.
i-Pr
I, 2001, 2711.
6) 87%
512
4 Section 325
Compendium of Organic Synthetic Methods, Vol 11
PC ~
C
H
1. MeMgBr
2.OMgBr2
NHBoc
Pietrantonio, S.; Bonini, C. Tetrulzedron, 2001, 57, 10039.
-G.;
NIi3 , 5 0 T
"%
Et+NH2
0 Tavlor.;Ide, N.D.; Silver, M.E.; Stephan, M.L. Syntlz. Cnnzmun., 2002, 31, 2391.
4% K20s(OII)204, NaOII , rt t-OBuC1, P O I 1 , HZO
J
i-Pr2NEt
Ph
-
4
87%
O 59%
011 Donoho e . T.J.; Johnson, P.D.; Helliwell, M.; Keenan, M. Clzenz. Commun., 2002, 20.78.
+'""
a t [ KzOSO,(OH)~]
Ph+CO2H
NHS0,R
chlorrunine-T.3 1120 Ph NaHCO,, rt
+
OH (1.6
m v v . Shdmless.K.B.ngew. '. .. Chem. Int. Ed., 2001, 40, 3455.
ph+co2H
NHSOzR 1) 96%
no C).. 1.
Lo
Farcas, S.;
,20"c,
2 eq S m h , THF 2. H30+
Tctruhedrnn Lett., 2000, 41, 1299.
69%
Section 325
Alcohol - Amide
513
Ts
92% ee
Giese, B.; Bxhosa, F.; StLhelin, C.; Sauer, S.; Wettstein, P.; Wyss, C. Pure Appl. Chem., 2000, 72, 1623.
SxnIz,THF cat Fe(dhm), * T *lB :l:s
(cH,),I
TB T so”” B s o q N 0
H a . ; Yun, C.-S.; Lee, Y. J.
0
Org. Cherii., 2000, 65, 621.
PhCHO ,Tic4
TMEDA , DCM
Y> 3
0°C
i-Bu
1-Bu
11l11111111
I ~011111111
HO
Ph
Ph (92 . . C m m i n s . M.T.; Chaudhary, K. Org. Lett., 2000, 2 , 775.
d
Ph
C,IIFONIlBr, 1.3 LiOH 4.4%KzOQ4.2 € 1 2 0 , 4 ” C
Oi-&
Demko, Z.P.; Bartosch, M.;
A
Ph
4% (DHQ)zPIIAL r-BuOII-H,O
..
8) 62%
JL 2
C3H7
*
Ph
Oi-Pr
4 01I
94% (95% ee) orb‘ iktt., 2000, 2 , 2221.
NaBH4, NiC12*6H 2 0 ,hexane
moist N203 I m . ; IIan, E.-H. Tetruhedron Lrtt., 2000, 41, 6479.
*
A
Ph
90%
Compendium of Organic Synthetic Methods, Vol 11
514
Section 325
1.2 q T F A , t-BuNC, 4 eq Py , DCM , 0°C Ir
2.si0z
BocHNT ('HO
t-Bu
BocHN
78%
OH Semnle. J . E , ; Owens, T.D.; Nguyen, K.; Levy, O.E. Org. Lett., 2000, 2, 2769.
,C02Me
0
NHAc
hv*PhH
~
AcH N
€1
0
75% (dr, >97:3)
GIlesheck.;Heckroth, 11.; Schmickler, H. Tetmhedron Lc:tt., 1999, 40, 3137.
C02Me
1.2 TsNNaCl , aq MeCN
c
1% KZOSO,(OH)~
Pringle, W.;
HOiiiiiiii
Hoiiiiiiii
NH Ts
12) 88% bothrac
(88
Sharnless.K.B. .. Tetrahedron L.ett., 1999, 40, 5151. 1. 1 . 5 q IDA ,TIIF, -78°C 2 1 . 5 q MoOPD, -78°C
0
Hara, 0.;Takizwa, J.-i.; Yamatake, T.; Makino, K.; Hemada. Tetruhedron Lett., 1999, 40, 7787.
% Bz
OH
1. TFAA , 11-IF 2. heat, NEt, 3. 2.5MNaOH
*
Y,
UoH N
I
Bz
Cossv. .I,Dumas, ; C.; Pardo. D .G,Eur. J. 01-8. Claem., 1999, 1693.
63 %
Section 326
Alcohol - Amine
515
SECTION 326: ALCOHOL, THIOL - AMINE NIBu
l.LDA,THF 2. PhCHO ,-78°C
QH
NHBu
QH
3. NaBH4, THF/MeOH
Pb
Veenstra.; Kinderman, S.S. Synlett, 2UOZ, 1109.
Nv
1. X 1 4 , PhH, reflux
Ph
Uucawa.
56% (synhnti = 2.4)
OH
2.10% HCl
PhI
r x
NHz
70%
Y,;Tsuji, C.; Miyazawa, E.; Sakamoto, T. Tetruhecfron Lett., 2001, 42, 2337. PhNMe, , hv , 1 d
PhCHO
* Ph'
Kim.;Mah, Y.J.; Kim, A.R. Tetrahedron Lett., 200Z, 42, 8315.
OH
cIIo 1. BrZnCH,COg-Bu T H F , O 0 C , 2 h vi-Bu I
NBnz
2.aqNH4Cl
.
AndrBs, J.M.;
Ph-
79%
OH
+
c0i-B~
NB n,
NBn, (78 22) 69% ; PBrez, A.; PBrez-Encaho, A. Tetrulzedron, 200Z, 57, 8521.
BnNtI, , LiC104
a
&p
a
m
MeCN ,reflux
95%
u ; VBzquez, V.; m r o . 1. ; Juaristi, E. Synth. Commun., 2001, 31, 3295
'OZEt
1. MeCOzEt ,MgN(i-Prh ether, 0°C
CN
2. MgN(i-Pr),
Nakalshima, T.; Mano, M.; Morikawa, 0.;Konishi, H. Chem. k t t . , 200Z, 602.
516
Section 326
Compendium of Organic Synthetic Methods, Vol 11
a-Zr(03PMe) 2(03PC6H4S03H)0.8 PhNHz, neat, 40°C , 2 0 h
Cunnl.;Epifano, F.; Marcotullio, M.C.; Rosati, 0. Eur. J. Org. Chem., 2001, 4149. .
I
MeLi , ether, -90°C 64%
OH
I
Bn
Band.; Huher, F.A.M.; Tveremvsky, V.V.; Bolesov, I.G. Tetruhedron, 2001, 57, 1593.
Do
PhNHz , CeCI3-7 H20-Nd
D
b
O
DCM,rt
75%
H "0,
, 831. Reddy, L.R.; Reddy, M.A.; Bhanumathi, N.; ~ S y n t h e s i s2001,
NHPh
P hNHZ ,H 2 0 p-cyclodextrin
Reddy, L.R.; Reddy, M.A.; Bhanumathi, N.;
*
D
H
82%
"'N H&
m Synlett, 2000, 339.
8 atm 112 , t-BuOK, i-PrOH ,rt ,4h
NMq
O
L,
RuC12(diphosphine) 1,2-diamine)complex
L
N
M
%
99% (92%ee) Ohkuma, T.; Ishii, D.; Takeno, H.; povori. R. J. Am. Cltem. SOC.,2000, 122, 6510. Ph
/
Pi
85% (90:lO E : Z , 97:3 er) Whisler, M.C.; Vaillancourt, L.; Beak. P. Org, Lett., 2000, 2, 2655.
Section 326
Alcohol - Amine
517
0"
1.1 eq PhN€12,reflux, 4 h
*
hexafluom-2-propano1
'"% NHfi
84%
Das, U.; Crousse, B.; Kesavan, V.; Bonnet-Delpon, D.; BCgue, J.P. J. Org. Chem., 2000, 65, 6749.
Charrada, B.; Hedhli, A,; Baklouti.
PhCI 1zN-P h
4Tetruhcdron k t t . , 2000, 41, 7347.
henzophenone , TiC14, Sin
*
57%
Ph
I
TIIF, 60°C , 3 h Ma, Y.;T h a w . Y.Org. Prep. Proceed. Int., 2000, 32, 567. 1.2.2eq S d 2 , 1% NX2, THF 2. i-PrN=CHPh * 3. 1130+
>'u.
80%
a!-
Machrouhi, F.; &my. J -1 .. Tetruhedron Lett., 1999, 40, 13 15.
NI14011 , inicrowaves
82%
Ph
NHi-Pr
%11
77%
8 min
hdstr6m.U.M.: Olofsson. B .: Sornfai. P. Tetrahedron Lett., 1999, 40, 9273.
90%
Done.:Fang, X.; Schroeder, J.D.; Garvey,
D.S. Synthesis, 1999, 1106.
PhNHz, Sn(OTf), ,ether
*
94% % ",,
Sekar, G.;
m.V.Y. J. Org. Cheni., 1999, 64, 287.
518
Compendium of Organic Synthetic Methods, Vol 11
Section 327
- %d r HQ
Bu,SnH ,AZBN ,PhH KflUX
NHOMe
54%
I
COzBn
COzBn
Naito.; Nakagawa, K.; Nakamura, T.; Kasei, A.; Ninomiya, I.; Kiguchi, T.
J. Org. Chem., 1999, 64, 2003.
-
SECTION 327: ALCOHOL, THIOL ESTER
Et
MesLi,THF -78”C, 1 h
. Kondo._Y.;
0
70% Asai, M.; Miura, T.; Uchiyama, M.; Sakamoto, T. Org. Zxtt., 2001, 3, 13.
@I(0H)OTs p-To1 Ahe, S.; Sakuratani, K.;
*
L p-Tol J. Org. Chun., 2001, 66, 6174.
CHC13 , =flux
O
T
S
67%
cat NIIPi , PhCN , 7 5 T cat Co(acach , 14 h Hara, T.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Clzenz., 2001, 66, 6425. 1. CIIZ=CHCOzMe, 75% Py-box 2.5% [ ( c ~ d ) I r C l ],~E t S i H , 25°C
\/“Io 5
6 Bn
2. H30+
OBn 50% (>95:5 syn:anti) Zhao, C.-X.; Duffey, M.O.; Taylor, S.J.; Morken. J.P, Org. k t t . , 2001, 3, 1829.
Section 327
Alcohol - Ester
LDA ,EtOAc, TIIF
PhCHO
519
-I% COzEt
Ph IIuerta, F.F.; BLckvall, J.-E. Org. Lett., 2001, 3, 1209.
>99%
1. CbMeSiH , 2 . 7 DuPhos 1.25% [RhCl(C02)]2 d C l z M e
A
2. PhCHO, -46°C 3. H30+
Zhao, C.-X.; Bass, J.; Morken. ,I.P. Org. Lea., 2001, 3, 2839. 1. In,TIIF, 0°C + rt 2. PhCI10,O"C , 4 h
OAc
Br
94% (>60: 1 syn:untQ
0 Ac
ardo. M.; Girotti, R.; Morganti, S . ; TroInhjni.
Lai,
86% (85:15 syn:unti)
c. Org. k t t . , 2001, 3, 2981.
1) 85%
(20
s.;
I
; Jasinski, J.P.; Reid, S.N.; Staples, R.J. Org. k t t . , 2001, 3, 4169.
/\ljsph
PhCIIO ,TiCh*NBu,
* P
0
h
V
S
P
h
u Matusrnoto, ; N.; Funakoshi, S . ; Manta, N. Synlett, 2001, 1959.
99% (86:14 yn:unti)
2
i-l'KIiO , 10%Me3A1 CHzc12, I t , 22 h
Smpura. I.; Nevalainen, V. Tetruhedron La., 2001, 42, 3905.
80%
Compendium of Organic Syii thetic Methods, Vol 11
520
Section 327
-2% HCl,(thf), ,toluene 16 h
OH
4) 79% R = adillnantyl (95 R ' Ishihara, K.; Nakayama, M.; Ohara, S.; Yamainoto. I I . Synlett, 2001, 1117. OTMS
PhCHO
-
QH -
yMe
*OMe
chiral Zr catalyst, toluene 94% (78% ee) C;II,OH ,0°C K o h a v a s L L ; IrAani, H.; Yamashita, Y.; Ueno, h ; Shimizu, H. Tetruhedron, 2001, 57, 8 1. 0 2 Ci -Pr PhCHO
i-PrCHO , 2% Y50(Oi-Pr),,
13% salen ligand ,DCM , MS 4,4
Ph
Ph Mascarenhas, C.M.; Miller, S.P.; White, P.S.; Angew. Chcm. 1n.t. Ed., 2001, 40, 601.
M]e+:
+Me
CQMe
,02
(>15
1) 70%
, O . l % Co(0Ach
5% N-hydroxyphthalimide 25"C, 15 h
* Me -zzMe
9
84% IIirano, K.; Iwahama, T.; Sakaguchi, S.; Lshii. Y, Che113. Commimn., 2000, 2457.
1. Zn , BrCH2C02Et,BFyOEt, 2. BzzO2 Chattopadhvay. A.; Salaskar, A. Synthesis, 2000, 561.
CO,Et
92%
Section 327
Alcohol - Ester
521
C I 12c12 , E t3N( GF ,3CIIzCh)2Sn 0 P h c Bucher, B.;
o
75 X80%
?‘sC1,50 min ,rt
H
TetrulzedronLttt., 2000, 41, 9617.
Fe3+-Montmorilbnite ,TsOH
76%
DCE, reflux
&OH
Choudary. B.M.; Chowdari, N.S.; Kantam, M.L. Tetlnlzcdrnn, 2000, 56, 7291.
20%
Lnb. T.-P.;
Feng, L.-C.; Wei, L.-I.. Tetrulieriron, 2000, 56, 7309. PhCHO ,TIIF, r t , 3 h
70%
*
20% PPh3
MLSV
P
h
Matsukawa, S.; Okano, N.; h a m o t o . ’I 1 Tctruherlrorr LcJtt.,2000, 41, 103. CgH &HO , 100 atm supercritical CIIF3
M%SD t-BUS
&
Tetrulzedrnn Lett., 2000, 41, 1931.
2.5% [RhCl(cod)]z , 6.5%R-BINAP laylor, S.J.;Duffey, M.O.; -.I.
,
.
>
.
9H
CIIZ=CIICOzPh , Et,MeSiII
PhCIIO
. .
. . .
t-B 46% (94:6 S:R)
. . Mlkaml.; Matsukawa, S.; Kayaki, Y.;
; -
t
0.2 [RBINOL-Ti( Oi-Pr)2C12]
I’h
A C O Z P h
E-
72% (3.4:1 sjn:unti) 8 7 7 e 34%ee Am. Cl~enr.Soc., 2000, 122, 4528.
Khau, V.V. Tetrulzedron Lett., 2000, 41, 3773.
Compendium of Organic Synthetic Methods, Vol 11
522
Section 327
pyB-Br S02Ar
.
SQAr
PbS -CQt-Bu
p --
p,,,\t~''
*
2. DIPEA , DCM Ar = 3,5di-CF3-qH3 3. PhCHO ,-78°C Corev.;Choi, S. Tetruhedron LL'tt.,2000, 41, 2769.
P
h
y SPh
COzr-Bu 97% (98:2 anti:syn) 90%ee
OMe
PhCH0
I
10%BINOL-Zr =tidyst bluene ,0°C
(8:92 syn:unti) 61% 93% ee Ishitani, H.; Yamashita, Y.; Shimizu, H.; I
C0,Et 82%
Kanai, K.; Wakahayashi, €1.; h n d a. 101-6'.L~jtt.,2000, 2, 2549.
8'
1. S d z ,THF , MeOII , 0°C
C%Et
2. aq NaCl , citric acid
Johnston, D.; McCusker, C.F.; Muir,K.; Procter. D.J, J. Chem. Soc., Perkin Truns. 1, 2000, 681.
* k
C
Q
E
t
65%
€10
C02Me
Ph (85 Loh, T.-P.; Huang, J.-M.; Xu,K.-C.; Goh, S.-H.; Vittal, J.J. Tetruhedron Lett., 2000, 41, 65 11.
Ph
15) 70%
Section 327
Alcohol - Ester
H
0
I1 0 cat Me-?,<& , H Z O ~ 0
OSiMe,
Py , MeCN , ALOH * OM StankoviC, S.; &penson. J .H. J. Org. Cherii., 2000, 65, 5528.
Lo
10% Cu(OTf), , DCE , i-F'rOH
"' 523
COzMe 71%
Ph
0
57% (28% ee, R ) Russell, A.E.; Miller, S.P.; m
n
. J.P.J. Org. Clzenz., 2000, 65, 8381.
1. Cl$HCO2i-Prt i-PiOK, I-I'IOH 2. NaBH-,CN, i-F'rO€I, 65°C
Cqi-Pr
= &H Grison.;Coutrot, F.; Comoy, C.; Lemilheau, C.; Coutrot, P. Tetruhedron Lett., 2000, 41,6571.
69%
Ghosh.;Kawahama, R. Tetruhccimn Lett., 1999, 40,1083 7
.
LiAlII(Ot-Bu)3, TIiF
Ph
COZEt
rt , 4 d reflux, 2 h Avers.T.A.erruhedron Lc.tt., 1999,40,5467.
85% 76%
524
Compendium of Organic Synthetic Methods, Vol 11
-
01I
Bakers yeast, DMSO COZEt
Section 328
- A
COzEt
aq EtOII, 2 5 h
aoH
67% (98%ee) Tetruliedron, 1999, 55, 7519.
Hayakawa, R.; Nozawa, K.; Kimura, K.;
lipase PS-C ,THF ,pII 7 lt,lh
i
88%
OzCPh Nair, R.V.;Shukla, M.R.; Patil, P.N.; Salunkhe. M.M. Synlett, 1999, 29, 1671. Also via:
SECTION 328:
Section 313 (Alcohol - Ciuboxylic Acid).
ALCOHOL, THIOL - ETHER, EPOXIDE, THIOETHER
%-
15% Pd(OCOCF3)z 18%(M. S.S.)iPr-SPRIX 4 eq p- henzoquinone DCM, rt , 2 1 h
OH
70% (70% ee) J. Ani. Cheiit. S O ~ .2001, , 123, 2907.
Arai, M.A.; Kuraishi, M.; Arai, T.;
r+ Me
Ph
I
BFL
*
NaOAc , DCE, t-BuPh , hv
OCnHi7 Kumar, V.S.;
OH J. Am.
Clieiii.
Soc., 2001, 123, 3842.
D
HO
74%
PhCI-IO , Sh Ph
DCM , heat MontinoiiUonite KSF
Yadav.;Reddy, B.V.S.; Kurnar, C.M.; Murthy, Ch.V.S.R. Tetruuhedron L m . , 2001, 42, 89.
90% Ph
Section 328
Alcohol
Lattanzi.;Sala, G.D.; Russo, M.;
Me
- Elher
525
COzBn
OTE s
1 . TiCh ,CHzClz , 0°C
Areino, N.; &.ss.L
66%
2 eq N2=CIICOzBn Zrc10,
/\CHO
7)
(93 Screttri, A. Syrrlett, 2001, 1479.
2. Ti(Oi-Pr)4
*
62% (* 5:1 dr)
For
Tetruherlron Lett., 2001, 42, 3637.
52% (56:M)
ori
Park, H.S.; Kim, S.H.; Park, M.Y.; lirm. Y.II. Tetruherhn Lett., 2001, 42, 3729.
e- , NaBr , MLOH
--(I 73%
011
Ellnson.;Feducovich, S.K.; Dmitriev, D.E.; Dorofeev, A.S.; Vereshchagin, A.N.; Nikishin, (3.1. Tetrulierlron Lett., 2001, 42, 5557.
L \
PhCHO ,Anherlyst- 15
Ph
88%
DCE, reflux , 2 h Ph
Yddd\t.; , . Keddy, B.V.S.; Sekhu, K.C.; Gunasekar, D. Synthesis, 2001, 885.
Ph
526
Compendium of Organic Synthetic Methods, Vol 11
Section 328
,,
J:.-i:5”CQ/// p
QH
HO
-a ,,,,/ , ~ B uPh” +
Ph
Bu
Ph 60% SPh 5% Grutladauria. M.; Aprile, C.; Riela, S.; Noto, R. Tetrulterlron LAN., 2001, 42, 2213.
f
sefi
10% Cp2TiC12, ’THF collidine*IICI , Zn
65 h
68% (58:42 dr)
Gansluer, A.; Pierohon, M.; Bluhrn, 11. Synthesis, 2001, 2500. &\
9H
/Ph
t-BuOOH, KH , DMF
* B UokrY YoIiO ”
BuQoI1 HO
78%
Denmark.;Ghosh, S.K.Angew. Chcm. Int. Ed., 2001, 40, 4759.
UoMe
BiC13, MeOH, r t
*
0°C , 3 0 inin
f%OH ,,
97%
-or-Baltork. I.; Tangestaninejad, S.; Aliyan, €1.; Mirkhani, V. Synth. Commun., 2000, 30, 2365.
Ph’OO
Fe(C10&, MeOH , i t , 1 h
t
oO”
87% OMe Salehi. PA;Seddighi, B.; Irandoost, M.; Behhahani, I.K. Synth. Conunun.,2000, 30, 2967.
5% [Rh(COhCl]z, 10
MLOH
TIIF, rt Fagnou, K.;
.
Org. Lett., 2000, 2, 2319.
‘“rff“
OMe
94%
Section 328
Alcohol - Ether
5 27
LDA ,TIIF, -78°C
"'"sQ ; Mafias, R.;
OMe
80%
Tetruheclron Lett., 2000, 41, 2549.
AlEtR , TEA , hexmes
*
Ti catalyst (or Zr catalyst)
+ ,,"
Et
OH
94% 1. Org. Clzern., 2000, 65, 3902.
Millward, &OMe D.B.; Sammis, G . ;
5% RuC13Q H,O, 0°C 4 eq NaIO4,4 min EtOAc/WCN/I-i2O
* €I0
OMe
*hQH "?,/
OH
63% Niimi, T.; Uchida, T.; Irie, R.; Kabuki. T. Tetruherlron D t t . , 2000, 41, 3647.
PhCHO a t Sc(OTf), , CHC13 Ph
12% Zhang, W.-C.; Li. C . 4 . Tetruhedron, 2000, 56, 2403.
+ bPh
4. excess SnI, , NII, , hv
Molander.; Kollner, C. J. Org. Clion., 2000, 65, 8333.
0
58%
70x91 %
528
Section 328
Compendium of Organic Synthetic Methods, Vol 11
Ph
1% VO(Oi-Prh , t-BuOOII, 0°C 1 .S% c h i d hydmxaiiuc acid , 6 h
Ph
Ph 96% (95%ee)
IIoshino, Y.;
J. Am. C h m . Snc., 2000, 1 2 , 10452.
L
e- , Nd-NaOII, MeOH
*
Ph
82% OH Clmson.; < . Feducovich, S.K.; Dorofeev, A S . ; Vereshchagin, A.N.; Nikishin, G.I. Tetruhcdron, 2000, 56, 9999. Ph
e
B
t
l OMpM
lE' ::ho
* BrioW
o
~
2.Zn(OTl),
p 85%
Matsumura, R.; Suzuki. T.; Sato, K.; Inotsume, T.; Hagiwara, €1.; Hoshi, T.; Kamat, V.P.; Ando. M. Tetruhedron Lett., 2000, 41, 7697. Also see Matsumura, R.; Suzuki. T.; Sato, K.; Oku, K.-i.; Hagiwara, €1.; Iloshi, T.; Ando, M.; Kamet, V.P. Tcwuhedron Lett., 2000, 41, 770. Ph,
8
0 . 2 BF,*OEtz
0
011
8
fi
OSiEt3
1.5 eq BnOzCY=H=N2
TIIF, -78°C Liu, Q.; BurtaD. D..1. Tctruhedron Lett., 2000, 41, 8045.
.
.
L h h d d L L ; Righi, G.; Oliveri, L.; Bovicelli,
75% P. Tetruhedmn Lett., 2000, 41, 10127.
65%
p
Section 328
Alcohol - Ether
529
,B F ~ ~ O E ~ Z
-’‘Me3
CHzClz , -45°C 2,6di-t-hutyl-4-me thylpyridine ;-
El-Said, N.A. J. Am. Cheiti. SOC.,I Y Y Y , 121, 10211.
SiMe3 56%
2. hv ,rt
Molander.;Machmuchi, F. J. Org.
8
toluene 2. LDA ,THF 3. H+
C77eni., ZYYY,
71%
64,4119.
‘“s/%
Saito, S.;Yamazaki, S.;Shiozawa, M.; m n o t o . 13. Synlett, ZYY9, 581.
Fan, J.-F.; WU.; Wu, Y.-L. J. Cheni. SOC., Perkin Zrurzs. 1, 1999, 1189.
I
530
Section 329
Compendium of Organic Synthetic Methods, Vol 11
0~
l
l
l
l
l
l
l
l
l
t
1.2%Co(III) sakncompkx
,
TBMB
OH
o1i 111111111
* €I0
96% (98% ee) Angew. Chem. Int. Ed., 1999, 38, 2012.
d>
Wu, M.H.; Hansen, K.B.;
21C14, NaBH4, TIIF
D O - 0 ,
t
rt,2h
'.
Chary, K.P.; Laxmi, Y.R.S.;Iuenear. D.S Synth. Coinmun., 1999, 29, 1257.
70%
REVIEWS:
"Free Radical Chemistry of Three-Membered Heterocycles," LiJJ,
Tetruhedron, 2001, 57, 1.
SECTION 329: ALCOHOL, THIOL - HALIDE, SULFONATE CK=H2CII,OH, 90°C P
h
d
o
(ClBu2Sn)z0, 18 h
93%
Synlett, 2001, 65 0.1 diamino alcohol of squaric acid PhL
B
Zhou, 11.; Lii, S.;
A
Ph
r
BH3*SMq, toluene, 0°C , 3 h
&.R... (2-
B
r
L1 8599% (99% ee ,S)
.
PhI(O,CCF3)2
* PhL
; Yang, T.-K. Tetruhcdron Lett., 2001, 42, 1107. , I 2 , ilq MeCN
DeCorso, A.R.; Panunzi, B.;
, 2h
t
95%
Ph Tetruhedron Lett., 2001, 42, 7245.
1. EtzAlI , hexme t-
2. PhCHO ,ether Han, Z.; Uehira, S.; Tsuritani, T.; Shinokuho, H.;
89% (>99: 1 unti:syn) Tetruhedron, 2001, 57, 987.
Alcohol - Halide
Section 329
53 1
1, , D C M , f l
*
cat Py-containing macrocycle Niknam, K.; Pooyan, M . Tetruhedron, 2001, 57, 6057.
I
A
80%
\2 /
T i c 4 , acetone , 1 h * 0
DCM ,1WC
N
W
71%
Shi. M,; Jiang, J.-K.; Chui, S.-C. Tetrulzerlron, 2001, 57, 7343.
or1 -
BH3*SM%, t o l u e ~ 110°C ,
-* &el 30% chird phosphoiuinide Ph
0
90 inin
0: 94% (82%e e , S)
Bdsavdlah.; .. , Reddy, G.J.; Chandrashekar, V. Tetruhedron Asyntm,, 200Z, 12, 685. 1. SiCI4, DCM ,-78°C , 4 h 10% chiral diazaphosphonmnide
Keymontl, S.; Ixgrand, 0.;Brunel, J.M.;
0
*
2. K F ,KII,PO,
% ,,,
77% (>99%ee) Eur. J. Org. Chctm., 2001, 2819.
0 F3CACOzEt
N
H H
. 10% chiral Cucoinplex ,,
ether, 0°C .-, it
C0,Et
80% (83%ee) Zhuang, W.; Gathergood, N.; Hawll, K.G.; Jorgensen, K.A. J. Org. Chem., 2001, 66, 1009.
L
Ph
1. TiCh-B u4NBr , DCM
2. i-PICI-IO
+
P
h
3. 1130+
Br 60% (>99:1 syn:nnti) Han, Z.; Uehira, S.; Shinokuho, H.; C),shima.K..Or&. Clzem., 2001, 66, 7854.
w
532
Section 329
Compendium of Organic Synthetic Methods, Vol 11
itcoP
NaBr , H 2 0 , InBr, ,40°C
pH 2 . 0 , 1.3 h
C3H,
*
&02H
s
78%
C3H,
OH Amantini, D.; Fringuelli, F.; Pizzo. F,; Vaccaro, L. J. Org. Chem., 2001, 66, 4463.
no catalyst (99 : 1) 99% + I n a 3 , pH. 15 (2 : 98) >99% 30 min Frineuelli. F.; Pizzo, F.; Vaccaro, L. J. Org. Client., 2001, 66, 4719.
ji
0.5% [Rh(S)Cy , Cy-oxo-ProNOP)
ozcCF3h
ca13
F3 C
20 atrn 112 , toluene 3O0C, 20 h
-1 F3
c
98% (97% e e , R )
Sakarnaki, Y.; Iseki, K. Org. Lttt., 2001, 3, 457.
;
PhCHO
CF31, hv , 12 h DMF ,-20°C + rt
cd 113
*
78%
MNMe2
MezN
PhCF'3 Me2N NMe2 Usher, L.C.; Estrella-Jimenez, M. Org. Zxtt., 2001, 3, 4275.
n;
A
Ph
1. CF3SiMe3,0.05 Bua+Ph3SnF2DCM , 0°C
SiMe,
2. PhCHO , BF,*OEtZ
* PhV
78% kfehvre, 0.;b i g a u d . T.: Portella. C. J. Org. Chertt., 2001, 66, 1941.
P F
h F
Smietana, M.; Gouvemeur, V.; Mioskowski, C. Tetmltedran Lett., 2000, 41, 193.
Section 329
Alcohol - IIalide
533
Ql:
1.2 10% eq TMSCl (SIIO),~ , CII,Cl, , 2 eq B'l'SP , 2 d
,,&
92%
2. IIC1MeOI-I BTSP = Me,SiOOSiMe, Sakurada, I.; Yamasaki, S.; Giittlich, R.; Iida, T.; Kanai, M.; Shihasaki. M. J. Am. Chin. SOC., 2000, 122, 1245.
uo"
Ph$H+ Br- , E M
76%
-90°C. 43 inin
% ,',,
Afonso, C.A.M.; Vieira, N.M.L.; Motherwell, W.B. Synlett, 2000, 382.
Br
1 . CH212, t o l u e ~ ~-70°C e,
*
2.
MeLi, ether NIIdC1, -70°C Bessieres, B.; Morin. C. Synlett, 2000, 1691.
4
Tt
&I
55%
1. TMSCl , DCM , 0"C, 2d 10% chiral phosphonamide
2. KF , KIIZPOI
J.M.; Buono, G. Tetruhetlron Asymn., 2000, 11, 4441. cslI1 ~
x
LiBr, I\mherly.\2-15, ~ 2h ~acetone -
~
;
~
-gr
W I I
97% Antonioletti, K.; Bovicelli, P.; Fazzolari, E.; Kiehi. G. Tctruhedron Lett., 2000, 41, 9315.
P *
.
17) 78%
(83
. .
Shlmlzu.,Kanemoto, S.; Nakahara, Y. Hercrocyclcs, h
w
o
Iz , Mn (salen) catalyst DCM, r t , 6 h
2000, 52, 117.
*
P
Naeimi, H. Bull. Chcrit. SOC. Jpn., Z9YY, 72, 1525.
h
O
L
I 71%
534
Section 330
Compendium of Organic Synthetic Methods, Vol 11
L
2. TiCh-Bu4NI, 1. PhCI-IO D C M , -78°C
3.H30'
Ph
i
P
h
v
P
h
89% (>99: 1 syn:unti) 01-6' Lett., . 1999, 1, 1383.
Uehira, S.; Han, Z.; Shinokuho, H.;
SECTION 330: ALCOHOL, THIOL - KETONE
Jw
2 eq CPzTiCI ,'I'I1FMeOI-I
OSiMe3
b-(
PI1
Ph
86%
J. Org. Chetn., 2VVZ, Mi, 1046.
Hardouin, C.; Chevallier, F.; Rousseau, B.;
P hCHO
LoH -2
*
0
Ph
,chirid ci'own ether, 0°C
cat Ce(OTf), , H,O-EtOH , 18 h
Ph
Ph
:J 85%(82%de)
Kohavashi. S.; Hmada, T.; Nagayama, S.; Manabe, K. Org. Lett., 2001, 3, 165.
Y
cyclopentanone 20% Lproline ,,CIIC13 72 h
OHC
'o.,,
1
1 J k
0
% ,,,
" J ',t,
1) 77% 20%ee
(2.5
95% ee List. B,; Pojarliev, P.; Castello, C. Org. Lett., 2001, 3, 573.
u
[( PPh3)CuH]6 , toluene
-4O"C, 1 h
@
+
Cbiu.;Zeto, C.-P.; Eng, Z.; Cheng, K.-F. Org. Lett., 2001, 3, 1901.
80%
Section 330
2. 1. B(OI-I)3 O . l M S, HzO m I ~ F0°C ,
SEN f-
TMS
(-+
Bode, J.W.; Carreira. E .M.Org. L.ett., 2001, 3, 15x7.
'rest B
oyT 535
Alcohol - Ketone
b
TMS
-%
acetone, MS 4,&, 5°C his-amnine ligarid , TIIF
.m;Silcoff, E.R.; Ito, 11. Org. L e t t . ,
2001, 3 , 2407.
62% (87% ee)
NaBII,, EtOIl , 10O"C,4 h aq dianine , PhB(OH),
P
h
v Ph
*
Ohtsuka, Y.; Koyashu, K.; Ikeno, T.;
>
CHO
Ph
5% ketoiminato cohalt complex
93% 95% anti 199% ee Org. Lett., 2001, 3, 2543.
0
1WuZn complex 36 h , -40°C
Ph
OH
I' (5 :1) 92% Yoshikawa, N.; Kumagai, N.; Matsunaga, S.; Moll, G.; Ohshima, T.; Suzuki, T.; Shihasaki.. . I Atn. . Chem. SOC., 2001, 123, 246G.
YIPll MS 4 w ,TI-IF, 15% R3PS 5% dinuclear Zn catalyst -35°C. 1 1 d
-
94% (90% ee) .Trost.;Ito, H.;Silcoff, E.R. J. Am. Chcin. SOC., 2001, 123, 3367.
Ph
536
Compendium of Organic Synthetic Methods, Vol 11
r
?Me
; Lam, Y.-F. Org. Lett., 2001, 3, 3535.
Ghorai, B.K.;
Section 330
OH
64%, 0.25% Rhz(cap)4 , PhH , reflux, 10 min 5% Rh2(OEt)4, YhH , retlux , 10 rnin 62% Hwu. J.R.; Tsay, S.-C.; Lin, L.C.; Chueh, L.L. J. A w . Cl?cin. Soc.,2001, 123, 5104.
(6.7 1) 77% (1 73) 66% . ; Sugae, T.; Ohtaka, A.; Takai, Y.; Tanaka, A,; Machino, C.; Kamhe. J . Am. Chem. SOC.,2001, 123, 5108. u/
1.5eq NaOMe
u/ 2.5 eq NaOMe
Sugoh, K.;
K;
LCIIO 5 % Co(dpm)2 PhSiH, , DCE , rt
Ph
*
)I&
Ph
70%
mph
Baik, T.-G.; Luis, A.L.; Wang, L.-C.; msche. M..1. J. Am. Chiwt. SOC.,200Z, 123, 5112. 1. PhCAO ,cat HNTf2 ether, -78°C
* 2. 1M HCl ,THF Ph Ph Ishihara, K.; Hiraiwa, Y.; m o t ( > . Ii, Synlett, 2001, 1x51
92%
Section 330
Alcohol - Ketone
A
4
PhCIIO, CHZCl2 5% VO(OSiPh),
-
Ph
537
*
,Me
Ph
Ph
Me
86% (8020 syn:unti) Trost. B.W; Jonasson, C.; Wuchrer, M. J. Ant. Client. Soc., 2001, 123, 12736. OSi(OMe),
chiral phosphine PhCHO , 10%~ AgF , BINAP derivative
MtOII 87% (7030 Jyn:ruzti), 90% ee Yanagisawa, A.; Nakatsuka, Y.; Asaknwa, K.; Kageyama, H.; Yainarn oto. €LSynlett, 2001, 69.
orr
5% Ru(PPh3)3IICl, THF
72% (56:44 syn:unti) Uma, R.; Davies, M.; Crkvisy, C.; GrBe, R. Tetruhedmn Lett., 2001, 42, 3069.
A
UBU
t-BuC€IO, 3% chiral Ca complex EtCN-?’FIT; , 20 h
Ph
=
Ph
74% (81% e e , R ) Suzuki, T.; Yainagiwa, N.; Matsuo, Y.; Sakamoto, S.; Yiunaguchi, K.; Shihasaki, M . ; U Tetruherlrnn Lett., 2001, 42, 4669.
+
2.2 tq SinIZ,THF ,rt , 4 h EtOzC+ CO2Et Liu, Y.;
Ph
Tetruhedmn LL’tt., 2001, 42, 5745.
COzEt
€* 1p 0 68%
Ph
Section 330
Compendium of Organic Synthetic Methods, Vol 11
538
1.;2;zIii;HF
/
@+ @
2. H,O+
4%
CN
H
H
77%
. . Kakluchl.; Fujioka, Y.; Yaniamura, H.; Tsutsumi, K.; Morimoto, T.; Kurosawa, H. Tetruhedron Lett., 2001, 42, 7595.
LaliC, G.; Petrovski, 2.; GaloniC, D.; MatoviC, R.; SaiEiC. R .N. Tetruhedron, 2001, 57, 583.
\
\
C0,Me
26) 78%
(74 66:34syn:unti Loh.;Feng, L.-C.; Wei, L.-L. Tetruhedron, 2001, 57, 4231.
UPh
PhCI-I0 ,Ti& , EtCN
PhL
I
-95°C
. . Shlmlzu.; Kohayashi,
-1O"C, 5.5 h
*
F.; Hayakawa, R. Tetraheriron, 2001, 57, 9591.
hv ,DMPBI , AcOH ,THF
Ph%,#\%\Ph
Ph
DMPBI = 1,3-dimethylhenziiilidazoliiie *
76%
AxPh
Ph
.. EL;Chiba, N.; Nakajima, A.; Suzuki, K.; Yoneoka, A.; Iwaya, K. flL,epawa. Synthesis, 2001, 1248.
96%
539
Section 330
PhCHO, 10% Zr(0t-Bu), , THF -2O"C, 2 d 80%
Hansch, M. Chern. Comrriiin., 2001, 1218.
OTMS
I' hCI I 0
50% '
Komoto, I.;
UPh
, PEG(OMefi, COz
%(or&
*ph
,5 o " c , 3 h
72%
Chern. Con11111m., 2001, 1842.
PhCE-10, Ti(Oi-Pr)*chiral Schiffhase
n -
DCE
C02i-Pr
Ph
e
62% (56% ee) Ilavashi. M.; Yoshimoto, K.; IIirata, N.; Tanaka, K.; Oguni, N.; Harada, K.; Matsushita, A.; Kawachi, Y.; Sasaki, H. Isr. J. Chenz., 2001, 41, 241.
0
OSi( OMe),
PhCIIO , cat R-BINM-AgF MeOH, -78"C, 1 h
Ph
64% (7 1: 29 syn:unti) 71%ee 40%ee Yanagisawa, A,; Nakatsuka, Y.; Asakawa, K.; Wadamoto, M.; Kageyarna, H.; W o t o . Bull. Chem. Snc. Jpn., 200Z, 74, 1477.
*$
%#,
1. T i c 4 , i-PrzNEt, E M , -10°C 2. i-PICHO , DCM ,-78°C
Me
MeO'
Calter.;Guo, X.; Liao, W. Org. Lett., 2001, 3, 1490.
%* % '/
% ' #,
N \Me
70% (74:26 syn,syn:syn,anti)
0a
Compendium of Organic Synthetic Methods, Vol 11
540
Section 330
ffI0
, x M
* 0
2
N
T
P B u ~, -78°C. 12 h
80% C1 NO2 UM.; Jiang, J.-K.; Cui, S.-C.; Feng, Y . 3 . J. Chent. Soc., Perkin Truns. 1, 2001, 390. 10% Cu-bis-oxzolidine ligand
c
~
~
ether, E ~ 10% Me2NPh ,rt
Juhl, K.; Gathergood, N.; ,!@ensen.
0
I
K.A. Ckcm. Conmun., 2000, 221 1.
PhCl ,reflux Id
*
t-B u 0 O t - B ~ 80%
Motherwell.;Vhzquez, S. Tetruhcrlron k t t . , 2000, 41, 9667.
*
WP.; Payne, A.H.; Waring, M.J.; Scott, D.A.; Lynch, V . Tetruhedron k'tt., 2000, 41, 9125.
O
H
\ O /N
C
0
acetone, 30% S-prohe* 2 ' DMSO
k s t . B.; Lerner, R.A.; Barbas In, C.F. J.
0 2
0
hi.
68% (76% ee) Cherri. SOC.,2000, 122, 2395.
Alcohol - Ketone
Section 330
1.
0
54 1
, 3 q T E l , , CEI,Cl, ,-50°C
2. € 1 2 0
- &LOH 46%
LaliC, G . ; Petrovski, Z.; GaloniC, D.; MatoviC, K.;SaiEiC, R.N. Tetruhedron Lett., 2000, 41, 763.
PhCHO
MeCHO , BFD ,ThDP Ph
pH 7 buffer
-
01I
BFD = henwylfonnate decailioxylase ThDP = thianun diphosphate
99% (92% ee) Eur. J. Org. Chern., 2000, 2161.
Dunnwald, T.; Demir, A S . ; Siegert, P.; Pohl, M.;
Ts
TS
win. S.W.; Chen, P.; Nikolic, N.; Weinseimer, D.C. Org. Lett., 2000, 2, 1193.
Ni(R) , TIIF, rt ,401nin
LCH0 +
Ph
Ph
Barrero.A.F.;Alvarez-Manzaneda,
L
O
H
89% E.J.; Chuhboun, R.; Meneses, R. Synlrtt, 2000, 197.
1 . PhCHO 'I'iOt-Bu2 , BINOL-
eIII$
2. R-mandelic acid II 0 Ph M d h r w a l d . O r g . Lett., 2000, 2 , 401 1 .
(9 1
5 ) 71%
Ph
Section 330
Compendium of Organic Synthetic Methods, Vol 11
542
1. 3% [CuH(PPh3)]6, PMHS , rt toluene , 3 0 h
&
CSHI 1
2. CsHIICHO ,Tic14
-Ic
72%
Chirsman, W.; Noson, K.; Papa, P.; Sclafani, J.A.; Vivian, R.W.; Keith, Tetruhedron,2000, 56, 2779.
-B.H.;
h
J.M.
S d z , PhCHO , THF ,-45°C
-
Ph
p
h
y
7
0
%
Mukaiyama, T.; Arai, H.; Shiina, I. Chezerri Lelt., 2000, 580.
'k
A( +phJy
chiral Ru catalyst , l O T , 1 di Ph
Ph
HCOOH ,NEt,
0
ori
0 11) 99% 12%ee
(89 99% a? Koike, T.; Murata, K.; W v a . T, Org. Lztt., 2000, 2, 3831.
4
Ph
0 1 . 2 q S d 2 , THF ,rt
82%
Ph
Zhou, L.;
Synth. Corrmun., 2000, 30, 597.
cat ZnBr2 ,DCM ,rt 8h
Tu.
c
t
91% OH Y Q ; Fan, C.A.; Ren, S.K.; Chan, A.S.C. .IChenz. . Soc., Pet-kin Truns. I, 2000, 3791.
Section 330
M
SiQ,
543
Alcohol - Ketone
1. PhCHO , 10% chiral phosphoranide DCM ,-78°C 2.
NaHCO,
Denmark.;Stavenger, R.A. J. h
Ph
i .
Cltern. Soc., 2000, 122, 8837.
92% ( 1 2 3 1 SIR)
oms
PhCIlO
dp,l
, 20% Pb(OTf)2, 1 d
24% a o w n ether, aq EtOII , 0°C
Nagayama, S.; Kohavas . hi. S. J. ,4111.
PhCIIO
7
* P
h
v
P
h
62% (90:lO vvn:cmti) 55% ee Chcrit. Soc., 2000, 122, 11531.
, Tic4 , NEt, , 2 d
HOu DCM ,-20°C
80%
Shi. M.; Jiang, J.-K.; Feng, Y . 4 . Org. Lxtt., 2000, 2, 2397. PhCIIO , chkal A1 catalyst
4
62%
DCM , r t , 43 h
Ph Simpura, I.; Nevalainen. V, Angew. Clieiii. In?. Ed., 2000, 39, 3422.
C3H$3I 0
Trost.
2
acetophenone , 5% c h i d ligand 10% EtZZn, 15% Ph3P=S
*
TIIF,MS 4A
Ph
C3H7
33% (56% ee)
B.M;Ito, H. J. Am. Cherrr. Soc., 2000, 122, 12003. PhCIIO , 2 eq BqSnII 0.1 CuCl ,ether , rt
*
V
P
Ooi, T.; Doda, K.; Sakai, D.; Maruoka. K. Tctruhr4ron Lett., Z999, 40, 2133.
h
72%
544
3 EmcloBn 'Livows phv 0
Compendium of Organic Synthetic Methods, Vol 11
Section 330
1. LDA ,THF , -78°C
OBn
*
2. EtCHO
B nO
B nO
B nO
(5 8 f(lm.; Hong, S.D. Tetmherfron Lett., 2000, 41, 5909.
42) 80%
PhCIlO , 10% SC(O3SC12€{25)3
Ph
10% IICl, H 2 0 , 2 7 " C , 3 11 *
82%
35% yield without IlCl Manahe, K.; Xohavashi. S, Tetruhedron Lftt., 19Y9, 40, 3773.
kI?.CHO, TiCl.+Bu3 0.05 TMSCl ,CH2C12
87%
Yoshida, Y.; Mahumoto, N.; Hamasaki, R.; Xitube. Y, Tetruherlron Lett., 1999, 40, 4227.
P h x c H o
Ph
, 8% chii-41Li cahlyd
* Ph
M M D S , 16%;1120, 1HF , 18 h Yoshikawa, N.; Yamada, Y.M.A.; Das, J.; Sasai, II.; J . Ant. Chem. SOC.,1999, 121, 4168.
L
t- BU
83% (85% ee)
1. R-BINOL-SEM, SnCh CIJzClz, -125°C 4 -78°C: 2. HI;-pyiidine , THF
* ~-BU%~~
Ishihara, K.; Nakamura, H.; Yamamoto. H , J. A m Chern. SOC.,Z999, 121, 7720.
87~95%
Section 330
Alcohol - Ketone
545
phvo
potassium monoperoxysulfate KzC03, pII 10.5 , MeCN , 0°C
I
Addm.;Saha-Moller, C.R.; Zhno, C.-G. J.
I
Org. Cliciiz., 1999, 64, 7492.
1. t-BuLi, T I I F , -78°C
mDMsL t
2. cyclohexanone ,I’I-IF -78°C
B
HZO, TIIF
-
lI+kI.-c”
M
%
S
i
72%
€30
Ph
Howell. A .R.;Ndakala, A.J. Org. Lttt., ZYYY, 1, 825.
GI%
+
e
co,I I
20% hC13 , 2 d ultrasound
(84 5 6 :44 syn:unt i Loh. T.-P.;Wei, I,.-L.; Feng, L.-C. Synlett, ZYYY, 1059.
I-IO,C 16) 95%
woSiMn, Pll
PhCIIO
u
. J. Org. Cliem., 1999, 64, 7547.
Stergiades, I.A.;
)$
-
a1 EtOH , -10°C
74% (3.2 : 1 syn:anti) 67%ee I-Pr i -Pr Kohavashi. S.; Nagayama, S.; Busujima, T. Cl~eiit.Lett., 1999, 71. +,% .
w
Compendium of Organic Synthetic Methods, Vol 11
546
PhCHO
Section 330
benzoyl fonnate decarboxyhse
* Ph
aq lwffer
70% (>99% ee)
Tetruhedron Asymm., 1999, 10,47G9.
PhCHO 20% chin1 his oxamline , 20 h 74% (3.2 : 1 syn:anti) 67% ee KobJuashi.: . . Nagayama, S.; Busujima, T. Tefruhcdron, Z999, 55, 8739.
PhC€IO
m.
+OTMS PI1
,H20
*
uph 87%
activated Monhnorillonite Ph K-10 clay T.-P.; Li, X.-R.Tetruhedron, 199Y. 55, 10780.
A 88% (GG% ee)
IIanzawa.;Tahuchi, N.; Saito, K.; Noguchi, S.;
Angew. Chem. Int. Ed., 1999, 38, 2395.
0
OlMS
PhCHO
,5MLiC104
MeN02,4 h
Sudha, R.;
*
(yPh
PhCHO , Et2A10Et,TIIF, 0°C z
85%
nPh
J. Ch~wi.Soc., Porkin Truns. 1, 1999, 383.
0 OH Mukaiyama, T.; Shihata, J.; Shimamura, T.; Shiina, I. Chern. Corrtmrtn., 1999, 951.
74%
Section 331
Alcohol
- Nitrile
547
PhCHO ,(B~3Sn)z
P& h,h€'
Bu,SnCl,, xi THF 0
Shihata, I.; Kawasaki, M.; Yasuda, M.; P,(\/~~''
81% (75:25 syn:anti) Chern. Lett., 1999, 689.
, E M ,-23°C
6 tw Ph+Br
OH
0
'I'iClz-Cu , t-BuCN , 3 h
94% (91:9 syn:anri) Mukaiyama, T.; Kagayama, A.; Igarashi, K.; Shiina, I. Chenz. Lxtt., 1999, 1157.
AlCI3 , PhCl , 106°C
/
mimwavcs , 3 min
/
+
o
73%
e
O
\ /
H
23%
Khadllkar.; Madyar, V.R. Synth. Coninrun., 1999, 2Y, 1195 REVIEWS: "Diastereoselection in Lewis Acid Mediated Aldol Additions," Chem. Rev., 1999, 95, 1095 "The Vinylogous Aldol Reaction: A Valuahle, Yet Understated Carhon-Carhon Bond Forming ; Zanardi, F.; M o n o . G.; Rassu, G. Maneuver," Chenz. Rev., 2000, 100, 1029.
SECTION 331: ALCOHOL, THIOI, - NITRILE
PhCIIO
3.5 eq IICN , it, pH 4 5 PVAI.entiapped R oxyni&ilane
t
f"
hiphasic, MTBE-hexane Ph*CN WH.; Capan. E.; Buthuher, A,; Vorlop. K.-D. Org. Lett., 2001, 3, 1969.
85% (95%ee)
548
Compendium of Organic Synthetic Methods, Vol 11
Section 331
3% Mn(dpm)3 , CPrOH , 1h 0 2
&,!nus.
,PhSR3
PJ Scott, D.A.; Fielding, M.R. Tetruherhn krt., 2001, 42, 4127.
*r
1. [InBr/C13CCN] /I,HO
2. H,O+
54%
*
70%
Nbhrega, J.A.; GonGalves, S.M.C.; Penne. C. Tetrulaerlron Lett., 2001, 42, 4745.
CHO
1. TMSCN , DCM , 3 6 h ,-40"C B u ~ P Ochkal , Al catalyst
01I
-
)r
Ph-
2. 2N MCl
6 CN
Ph
97% (97% ee) Hamashima, Y.; Sawada, D.; Nogami, H.; Hanai, M.; Tetruhedron, 2001, 57, 801.
1,
1. TMSCN , 20%JTi(Oi-Pr), , J X M
PhCI-IO
chird Schiff base , -40°C
2. H+ Y ~ I I2.-€1.; ~ , Wang, L.-X.; Zhou, Z.-H.; Zhou, Q.-L.; T Tetruhedron Asyr,lm., 2001, 12, 1579.
+CN
1. CeC13 , TIIF
~
98% (70% ee)
Ph
~ D PC . - C .
&CN
+
L
Ph
P 11 (15
Dalrrozzo.;Bartoli, G.; Bosco, M.; DeNino, A.; Procopio, A.;
N
--
2. LiBII, Ph
C-
85) 75% Samhri, L.; Tagarelli, A.
Eur. J. Org. Chent., 2001, 2911.
IICN ,pHS.O, 1 , C , 12h R-hydroxynikile lyau:
Gerrits, P.J.;
H
O
a
\ /
Y
72% (86% ee)
N
Marcus.; Birikaki, L.; van der Gen, A. Teti-uherlronAsymm., 2001, 12, 971.
Section 33 1
PhCHO
Alcohol
549
- Nitrile
----
1% Li-R-(+)-BINOL TMSCN , 5 rnin
QmfS
h
96% (56% ee,S)
Ph+CN Ilolmes, I.P.; Kanan. H.B. Tt.tl-uh~~drnn Lett., 2000, 41, 7453.
xcN
(0
1) 95%
Ward.;IIrapchak, M.J.; Sales, M. 01-8.Lett., 2000, 2, 57. BlCIIzCN , 2 TIIF
LXI
87%
SI~II,
Tctmherlron Lett., 2000, 41, 3039.
PhCI I 0
YOU,J.-S.;
Me,SiCN , Ti(Oi-Pr), , 2 d
--
xcN 67%
cat p-amino-alcohol sulfonato derivatives Ph DCM , MS 4 i i - ; Choi, M.C.K. C h ~ l Conmiin., . 2000, 1963.
1 . TMSCN ,YC13(R-pyliox)z
PhCHO
2. 1 MIICl
77% (80% ee) CN pyhox = hk-(oxazolidinyl)p).rid~e Asmnall. H.C... GreevesI . N.; Smith, P.M. Toti-uhedron Lett., 1999, 40, 1763.
Ph
(Yo
10% I'(KNCII2CH2)3N , MeCN 2 . 2 t ~ MgS04 l ,25"C, 4 h
*
Dm 94%
Kisanga, P.; McLeod, D.; D'Sa, B.; Verkude. J, J. Org. Clzeni., 1999, 64, 3090.
I'h
A
10% Ce(OTf)j , NaCN
M K N , 70°C. 1 d
CN 011
70%
Iranpoor. N.; Shekarriz, M. Synrh. Cmnniiin., 19Y9, 2Y, 2240.
+
CN
12%
Section 332
Compendium of Organic Synthetic Methods, Vol 11
550
-
SECTION 332: ALCOHOL, THlOL ALKENE Allylic and benzylic hydroxylation (C=C-C-1-1 Section 41 (Alcohols from Hydrides).
-f
2
LDA, THF ,-78°C
C=C-C-OII, etc.) is listed in
+
HO-CN
4 eq ALOH , 5 inin Fleminp.;Wang, Q.; Steward, O.W. J. Org. Chem., 2001, 66, 2171.
u
83%
-b Ts
TsBr , AIBN , toluene
CsH11
90"C13 h
1
u, KO, B.-S.; Ha, Y.-€3. J. Org. Client., 2001, 66, 3630.
-P-
75%
OTMS
i-PiCHO ,TIIF, it , 1 d
OEt
,
Bluet, G . ;
I
*
chiral ainimniuin lluoride
I
-
70%(20%ee) J. Org. Clieni., 2001, 66, 4293.
65% (90%ee) Oppolzer, W.; Radinov, R.N.; El-Saved. E, J. Orhp. Client., 2001, 66, 4766.
CaH13Y-Y Br
CICI, ,NiClz , DMF ,rt
0
Trost.;Pinkerton, A.B. J . Org. CIwnt., 2001, 66, 7714.
9 70%
Section 332
55 1
Alcohol - Alkene
1Y k
C3F7
20% PhCHO
TMSO
1-1B- 0
-
,EtCN, -78°C
,syiinge pump
I
1:2(E:z)
71%
u; Wei, H.-X.; Phelps, B.S.; I k k i s s , D.W.; Kim, S.H. Org. Zxtt., 2001, 3, 823. CHO
CI-I2=CIICN,TCI4 Bu4NBr, E M , 20°C
Shi. M.; Feng, Y . 3 .J. Org. CIwnr., 2001, 66,406. (i
{:
OJON(
NOC 0, I. BuLi, pentane (-)-spmteine , -78°C +
2. TiCl(Oi-Pr), , -78°C 3. i-PICIIO , -78°C
MqSi
i-Pr)
,,,,+'
MqSi
i-pr 76% (>95% ee) Schultz-Fademrecht, C.; Wihheling, B.; Friilich, R.; Boppe. n. Org. k t r . , 2001, 3, 1221. n
Koh, J.H.; Larsen, A.O.; GaenC. M.R. Org. Zx:tt., 2001, 3, 1233.
Denmark. S.E.; Yang, S.-M. Org. Lc)tt., 2001, 3, 1740.
77% conversion (77% ee)
Section 332
Compendium of Organic Synthetic Methods, Vol 11
552
p
h
<
y CIIO
,5% c o complex
CIIC!, , -20"C, 2 d
0
P
h
G Ph
0 Kezuka, S.; Ikeno, T.; Xamada. T, 01-8. Lftt.. 2001, 3, 1937. excess
MezSCHz
90% (88% ee)
*
91%
TIIF, -10°C: -+ rt 0 HO Alcaraz.;Cridland, A.; Kinchin, E. Org. Lett., 2001, 3, 4051. 1. I-lB(c-heX)z 2. EtzZn
-
(36H13
71% (86% ee, S)
3. chiral N,O-ligand PhCHO Dahmen, S.; Brise, S. Org. Lztt., 2001, 3, 4119
Br
=
(m
C6Hl3
S% (Ph,SiXV, PhCI-10
DCE, 80°C
OH
-
94%(9-1 Z E )
Br,&
Trost.;Oi, S. J. Am. Cherrr. Soc., 2001, 123, 1230.
0
Ph
-L
l'hCII(OM~)~,l'MSo'I'f 2,hili-t-Bu-pynuline PhMe Si
CHzClz, -78°C , 1 h
Ph
88%
D.C,; Badine, D.M.; Gottscholk, T. Syrilett, 21101, 1909.
i l
1. LDAKOR , THF, -78°C
Bu
OBn
2.4 q B u L i , TIIF,0°C LIDAKOR ,TIIF, -78°C
-
it "+OH
-
5°C
OH
70~55%
s5 '51 'I'hurner, A.; WF.; TGke, L.; Mordini, A.; Valacchi, M.; Reginato, G.; Czira, G. Tetruhdron, 2001, 57, 8173.
Section 332
Alcohol - Alkene
553
OH
1. (r12-p~ope~'e)Ti(Oi-A.)2 1111111111
2. PhCIIO 95% (75 : 25 E:Z) Okamoto, S.;Teng, X.; Fujii, S.; Takayama, Y.; Suto. F.
J . Am. Chenz. Snc., 2001, 12.3, 3462.
h-
sugar--o
0
0.2 DABCO, H =J*( TIIF, 2 d> s u g a r 4
@ OH
0
Kr&uJ&.;
Kannan, V.; Ilnngovan, A.; Shaima, C.V.M. Tetruhedron Asyrnnt., 200Z, 12, X29.
NO2
91% (40%de ,R )
Kang. S.-Y;Ryu, H.-C.; Hong, Y.-T.; Kim, M.-S.; Lee, S.-W.; Jung, J.41. Synth. Conimun., 2001, 31, 2365.
1. 2-( lithiomethyl)-l-methylnnidau,le + chiral I i a n i d e , TNF
96% (93% ee)
2. H,O+ Idill, S.O.N.; Fettersen, D.; Amedjkouh, M.; Ahlhere. P. J . Chent. Soc., I'erliin Truns. 1. 2001, 3054.
Takai. K; Kokumai, R.; Nohunuka, T. Cherri. Conrrrirtn., 2001, 1128.
b
84%
Section 332
Compendium of Organic Synthetic Methods, Vol 11
554
CH3CHO
1. B r u C O z M e ,In ,
THF , HC1
2.DBU ,F%H
*
?TM
64x881 (93:7 E:Z) Cha, J.W.; Pae, A.N.; Choi, K.I.I.; Cho. Y.S.; Koh, H.Y.;Lee. E. J. Chcni. SOC., Perkin Truns. I , 2001, 2079.
87% ( 1 . 9 1 ) Wendling, F.; JVliesch. M, Org. L.ett., 2001, 3 , 2689.
m
II
CHO In,DMF,rt
SiMe,
89% Lee. P.H.; Bang, K.; Lee, K.; Lee, C.-11.; Chang, S. Tetruhedrun L d t . , 2000, 41, 7521.
Mn ,1076 CfiTiClz 2,4,6-collidine*HCl THF
Gdnsduer.; . .< Pierohon, M. Synlett,
20011, 1357.
u; Wei, I-I.-X.;Gao, J.J.; Cuputo, T.D. Tctrdierlron Lett., 2000, 41, 1.
75%
555
Section 332
7, \
0
Ag:KI, AcOH reflux, 30 min
0
O
g
0
-
Sharehi.;Aghapour, G . J. Org. Cliein., 2000, 65, 2813. 10% PhCIIO , 10% Sn(Oi'),
QH
CHZCI,, 0°C , 2 h I
78% (4911, E/z) Sumida, S.-i.; Ohga, M.; Mitnni, J.; J'Jokaini. J . .I. Am. Clzenz. Soc., 2000, 122, 1310.
Kim, M.S.; Kim, T.Y.; Lee, K.Y.; Chung, Y.M.; Lee, I1.J.; Kim. J.N. Tetruhedron Lxtt., 2000, 41, 2613.
LautLns.;Renaud, J.-L.; Hichert, S. J. a
.
92% (>98% de) Am. Clreni. Soc., 2000, 122, 1804.
PhCHO , S% PdCz(PPh3)2 IICI-SIICI~ , DMF ,rt Chatlg, II.-M.;
1
C.-FLClrg. Lett., 200fJ, 2, 3430.
>99%
556
Compendium of Organic Synthetic Methods, Vol 11
Br
P hCHO
In , 1120
Section 332
Br
'
* ph+% Lu, W.; Ma, J.; Wang, Y.; Chan, T.H. Org. LEtt., 2000, 2, 3469.
f f Y
v
2. NaOII
* ,11202
1
II
- . . Laldlewlcz.; Krczemimski, M.P. Org. Lett., 2000, 2, 3897. Et02C-CHO , 10% Pd catalyst DCFJtoluene , 6O"C, 4 h
PI1
=
97% (88% ee)
Org. Lm. 2000, , 2, 4059.
Hao, J.; Hatano, M.;
PhCIIO , 10% Ni(cod)2 Me
-
Ph+ph
20% PCy, , 2 BE t3 toluene, 23°C IIuang, W.-S.; Chan, J.; Jamison. T.F, Or$. Lett., 2000, 2, 4221.
7
,cat N i ( a ~ ; l c ) ~
P hCI 10
M q B , TI-IF, 2 11 Kimura, M.; Shihnta, K.; Koudahashi, Y.; Tainaru.
A
Ph
-
-78"C, 2 h
76% (77:23)
TP 56% (20:l E:Z)
Y.Tm-uherli-onL m ,2000, 42, 6789.
CM2=CIIMgBr, CeCl, , THF SiMq
fi
* & Ph
SiMe3 Bonini, B.F.; Comes-Franchini, M.; Fochi, M.; Mazzanti, G.; Ricc.i.; Varchi, G. Synlett, 2000, 1688.
60%
Section 332
Alcohol - Alkene
K =CRI
557
c~H7(B >
1. sec-BuLi, TMEDA ether, -78°C
N(i-Prh
2. Ti(Oi-Fr), ,-78°C 3. C$&IIO ,ether -78°C0°C
N(i-Prh
0
Mark6.IE; Leroy, B. Tetr-ul?crlronLxtt., 2000, 41, 7225.
1. q2-C,II6-?'i(Oi-Pr), , ether 2. EtCIIO, ether/ffII'
*KO
*KO$2
3. €1+
SiMq
K* = camphor-hued auxiliary 95% (97:3 S:R) Suzuki, D.; Urahe, 11.; $at(). I'. Angew. Cheni. b it. Ed., 2000, 39, 3290. ser-BuLi/(-)-spaiteine ,ether -9O"C, 6 h
*
1 0
,,,,,,,,85%(62%ee)
or1 ; Vrancken, E.; Mangeney, P. J. C17c~l.SOC., Perkin Truns. 1, 2000, 3354.
Youn, S.W.; Park, I1.S.; Kim. Y .I-I. Climr. Cnrrirrzrin., 2000, 2005.
&
OPMB
OPMB
2
MeZZt1, DCE , L*
S% Pd(MeCN)2C12, heat
* G
I,* = S-t-BuSDII'OF
Lduttns.; . Hiehert, 1
.
S.; Renaud, J.-L. O q . Lett., 2000, 2 , 1071.
O
or1
P
M
OPMB
87% (91% ee)
B
558
Section 332
Compendium of Organic Synthetic Methods, Vol 11
PhI
Anwar, U.;
1. DMF , 10% Pd(0Ac)z tris(2-fury1)phosphine
Ph
2. In ' M
H
e
0
~
-*
C
Ph%
O
64%
OMe
u; Raspitiini, M.; Savic, V.; Sridharan, V. Chem. Commun., 2000, 645.
oo 1.2
2 y L D A , 5 y DBU, T H F 78% (95% ee) rt,ld Sodergren, M.J.; Bertilsson, S.K.; Andel 'sson. P.G, J. Am. Chern. Soc., 2000, 122, 6610.
PhCfIO ,70% LiCIO,
Jm2Et 15% DABCO, ether O"C,20h
Kawlunura, M.;
C,H &€I0
'
'
% h'€
81%
TotrulzorlronLdt., 1999, 40, 1539.
BH
1. MLCCI, ,CrCI,(Mn) , THF ,r t 2. LDA
Falck.
CO2Et
*
'7"15
J.B;Barina, D.K.; Mioskowski. C.; Schlama, T. Tctruhcrlron Left.,
de Sousa, S.E.;
1999, 40, 2091.
; Steffens, 1I.C. Tetruherlron Lett., 1999, 40, 8423.
OH
TIIF, MS 4A,~t 2.PhMe, 5 % B H T , 190°C 3. M q N O , PhH ,XO"C
Batev.;Thadani, A N . ; Lough,
1111111111
HO
HO 75) 80%
A.J. J . Am. Chem. Soc., 1999, 121, 450.
559
Section 332
-
yuan, L.G.; -an.
100°C C~H&KCIC~H ~, .5% Pd(OAc), , 2 t-BuOAc
*
DMF . 2 0 h
V . . Y, ' m. ( >to. y.J. Ani. Cheni. Soc., 1999, 121, 3545
CIJO
, 19 h
-/-SnB"3
Ph
L-
BF3.0Et2, toluene
Ph+
Luo, M.; Iwahuchi, Y.; Hatakevaina. S. Chcni. Corriinun., 1999, 267.
PhCHO
92%
LSnBy , PhCF3 S-BINOL-Ti(1V), i-PrSBEt2, -20°C
Ph+
y u . C.-M,; Lee, S.-J.; Jeon, M. J. Clwrii. Soc., Perkin Truns. I , 1999, 3557.
81% (98% ee)
1% Ru(md)(cot) , PEt3 hexane , 20"C, 4.5 h
94% (97% Z) Sate, T.; Komine, N.; IIirano, M.; &va.
S. Cltenz. Lett., 1999, 441. 0 1I
__
1 . Me,CuLi/MeMgBr-CuBr-DMS
C0,Me
2. PIICIIO
Wei, K-X.; Willis, S.; Also via:
69% (95/1 UE) Synth. Coniiiiui~.,1999, 2Y, 29.59. Section 302 (Alkyne - Alcohol).
560
Compendium of Organic Synthetic Methods, Vol 11
Section 335
SECTION 333: ALDEHYDE - ALDEHYDE NO ADDITIONAL EXAMPLES
SECTION 334: ALDEHYDE - AMIDE
PHO OMe Banfield, S.C.; England, D.B
CHO
0
N-Ac NAc
69%
Fuchs, J.K.; Funk. K.1, Org. Lett., 2001, 3, 3361
OYPh Boto, A.; IIernindez, R.;
. T ~ ~ u k e d r Lztt., c ~ n 1999, 40, 5945.
SECTION 335: ALDEHYDE - AMINE
Section 338
Aldehyde - Halide
56 1
Me
Ph
+
12) 70% 4-1 a Jen, W.S.; Wiener, J.J.M.; MacMillan. D.W.C. J. Anr. Cl~cni.Soc., 2000, 122, 9874.
SECTION 336: ALDEIIYDE - ESTER
CDzMe
-
CO/IIZ , superaitical COZ cat P @ - c ~ I I , - c ~ F , , ~ *
0 1IC
cat Rh(acac)(C0)2 , 80"C, 11 h 98% (48% conversion)
IIu, Y.; (:hen, W.; Osuna, A.M.B.;Stuart, A.M.; Hope, E.G.; Chem. Conitnun., 2001, 725.
SECTION 337: ALDEHYDE - ETHER, EPOXIDE, THIOETHER
c~IO
Ph
1 . PhS(O)CI-I(Cl)Li 2. 5 PhSII , 7 t-BuOK 98x73%
C-BuOII,TIIF, it , 10iiiin * phdSPh Satoh. T.; Kuhota, K.-i. Tc.triilieilron Lcjtt., 2000, 41, 2121.
SECTION 338: ALDEHYDE - HALIDE, SULFONATE 1. IPy2BF4, DCM , hv , rt , 12 h
91%
~
H 2. II,O+ €1 Gonzilez-Bohes, I:.; Annthouju, S.R.; Garcia-Martin, M.A.; GonzBlez, J.M. Angew. Chent. Int. Ed., 2001, 40,33x9. D
O
; . J-
c1
176 2.6-lutidine-IIC1, 3.5% HCl C3II7-CHO Bellesia, F.; De Buyck, L.; Tetruh~4ron,2000, 56,7507.
t
DCM , 65°C C,H, X I 1 ; I,ihcrtini, E.; Pagnoni, U.M.; Roncaglia, F.
59%
0
562
Compendiuni of Organic Synthetic Methods, Vol 11
Section 341
-
SECTION 339: ALDEHYDE KETONE
C,H &H2CH0, MeCN ,reflux 10% Et2NSiMq
"".+
66% CHO Uapiwara. I.l; Komatsuhara, N.; Ono, €1.;Okahe, T.; Hoshi, T.; Suzuki, T.; Ando, M.; Kato, M. J. Chem. SOC., Perkin Truns. 1, 2001, 316.
/L
1. P B u ~, TI-IF , -40°C
2. SnlT2 c1 3. 1M N C I * PhW C H O 80% Mdedd.; . . Huang, Y.; Hino, N.; Yamauchi, Y.; Ohmori, H. Chem. Commun., 2000, 2307. Ph
II
1. LDA , ether , -78°C 2. HCO,CH,CF, , -78°C
Org. Lett., 1999, I, 989
SECTION 340: ALDEHYDE - NITRILE NO ADDITIONAL EXAMPLES
REV IE WS : "Cyanohydrins in Nature and the 1,ahoratory: Biology, Preparations and Synthetic Applications," Grecorv.R.J.H. C h m . Rcv.. 1999. 99, 3649.
SECTION 341: ALDEHYDE - ALKENE For the oxidation of allylic alcohols to alkene aldehydes, also see Section 48 (Aldehydes froin Alcohols).
Aldehyde - Alkene
Section 341
563
OHC
CHz=CIICHO, 4% RU acllyst
-
DCM, 25"C, 12 h
Ho$
.
6
..yJ
70%
Org. LPtt., 2001, 3 , 1451.
Ph-OH
10% Pd(OAc)z, 20% PPh, 2.4 BEt, , TIIF, NEt, Licl
Kimura, M.; Horino, Y . ;Mukai, R.; Tanaka, S.; 'Jamam. J. Am. Cham. Soc., 2001, 123, 10401.
GH13
HO] CHO
=
-
Y.
Me,PhSiH, 40 atm C O , 4 0 T , 1 d
O H ~ i M e $ h 7 8 %
z
[R h+(cod)(r16-C&I $-Ph3)] C6H13 Okazaki, H.; Kawanami, Y.;Yoin:unoto. K. Cheni. Lett., 2001, 650. 1
N-NHTs
%J
2.5 eq PhMgBr
* Ph
CHO
75%
Chandrasekhar. S .; Reddy, M.V.; Reddy, K.S.; Kamarao, C. Tetruhedron ,!.eft., 2000, 41, 2667.
I
63 % Parsons,E,. I ; Thomson, P.; Taylor, A,; Sparks, T. Org. k t t . , 2000, 2, 571.
Compendiuni of Organic Synthetic Methods, Vol 11
564
Section 341
%CHO
Higashino, T.; Sakaguchi, S . ; -Orb'.
h t t . . 2000, 2, 4193.
C H Z S I I O A c , Ba(OH)2 I
P hCHO
CHO
Ph
TIIF, heat , 10 h Mahata, P.K.; Barun, 0.;IliL H.: J-p. . . Lt Synlett, 2000, 1345.
-
7 -
Kh(CO)z(acac) , PhMezSiH
78%
SiMqPh
Ph€I, CO ,90"C, 14 h ; Itoh, K. Tctruherlron Lett., IYYY, 40, 4703.
Fukuta, Y.;
65%
+
(cod)KhI-'hBPh, ,60"C P(OPhh ,CHZClz , 2 d 6 atin C O , 6 ntm Hz van den Hoven, B.G.;
A
Ph Bharathi, P.;
J. Org. Client., 1999, 64, 3961. 1 . Tic4 , DCM, NEt,
* CHO
2.1120 Org. Lett., 1999, I , 857.
0.2 pyirolidine , 0.1 PhCO2N
Bu-CHO
toluene, ZO"C, 14 h
xr
78%
Ph
-
IShikdWd.; . , . Uedo, E.; Okada, S.; &it(>. S , Syrtlett, I Y Y Y , 450.
Bu
79%
REVIEWS: "The Silyloxy-Cope Rean'angement of Syn-Aldol Products: Evolution of a Powerful Synthetic Strategy," w i d er. C, Synktt, 2001, 1070. Also via f%-€Iydroxyaldchydes: Section 324 (Alcohols - Aldehyde).
Section 343
565
An~ide- Ainine
SECTION 342: AMIDE - AMIDE
#L mCoZMe NIIAc
1. ~-NsNCI~/MLCN 2. XJ NilZS03
LL&;
C02Me
Ph
Ph
~ H N s - ~ "%
t
Kim, S.H.; Wei, I-I.-X. Tctruhedi-on Lc.tt., 20UU, 41,8609.
0
8 y S m 1 2 , TIIF 16 C X ~R-BINOL 32 eq 'IMEDA , 411 -78°C , 30 min
/
Me
Me
70% (71% ee) 2w0 Kikukawa, T.; IIanamoto, T.; Inanaca. J. Tc,truhcclr-on Lett., ZYY9, 40, 7497. Section 312 (Cxboxylic Acid - Carboxylic Acid) Also via Dicarhoxylic Acids: Section 350 (Amines - hnines) Dialnines
SECTION 343: AMIDE - AMINE
p
-
--
t-BuCIIO, NaCN, A d 1 1
H2N-lfNH2
1 1 2 0 , 70"C, I d
0
'-"";7(, m
z
y
N
H
2
0
93% (>99: 1)
n Dielemans, ; H.J.A.; Elsenberg, 1I.L.M.;
Boesten, W.1I.J.; Seerden, .l.-P.G.; Kaptein, B.; Moudy, H.h4.; Kellogg, R.M.;
A NI/"A
Org. Lett., 2001, 3, 1121.
PhNIIMe , DCM, rt 10% Ni(C10,),6 II,O his-oxazoline ligand
Zhuang, W.; IIazell, R.G.; m n s e n .&(I
ph\
/Me
JJ
76% (88% ee) Chcm. Conwiin., 2001, 1240.
566
Compendium of Organic Synthetic Methods, Vol 11
a A,,
Et,
1. Et,AICI, MeCN *
w
u
Ac C02Et
62% (75:25 anti:syn)
. M.; Niwa, Y. Tetrahedron In.tt., 2001, 42, 2829.
N -Ts
yP
E * , C Y
2. AcQ
E0,C
Section 343
PhNIIMe , acetone, rt
86%
p-cyclodextiin, 1 1 0 , 1 d
Reddy, M.A.; Reddy, L.R.; Bhanumathi, N.; Rao. K .RCherir. I d t . , 2001, 246.
AJNG
C5Hl 1
Ishihiua, H.;
N H /J ether, -78°C
CllPirt.
C5Hll
Lett., 2001, 980.
86% truns
9 0.s 9 N D YN 2eq
,Id
BuLi ,‘HIF , -78°C
0 Hori, K.; Sugihara, H.; J@. Y.N.:-
I
rt
0
Tetruhedron LEtt., I999,40, 5201.
PhI, PdlC ,NEt, , MS 4A 800 psi CO , 100 gpi Mz 120°C
87% Ph 0
Lin, Y.-S.;
82%
Angew. Chcri~Int. Ed., 2001, 40, 719.
Section 343
567
PLlnide - Amine
n
-
23% 44% Hadden, M.; Nieuwenhuywn, M.; Potts, D.; Stevenson. P.J.; Thompson, N. Tetruhedron, 2001, 57, 5615.
....
1111,111
m B ( O W 2 Ph
P
B nN€ICH2CH2NHBn MLCN , 80°C. 2 h
3:) 76%
Ph
Petasis. N.A.; Patel, Z.D. Toti-uhcrlron Lxtt., 2000, 41, 9607. 0
0
Q Ph
‘o\%N
Me0
PhNH, , TIIF
45% OMe Alcaide.;Almendros, P.; Ar-ngoncillo, C. Cliern. Conirnun., 2000,757.
Bu
=
I
Bn
NHBn
Fb
OLi
Shindo.;Oya, S.; Murakami, K.;
Snto, Y.; Shishido, K. Tetmhedron Lett., 2000,41, 5943.
568
Compendium of Organic Synthetic Methods, Vol 11
Section 344
-*& HZN
I . Pd(OAc),, D P E A , DMF , PhI
2.10% TFA, CII2Cl,
ph d
8
4
%
Wanp.; Huang, T.-N. Tetruherlron LJtt.,ZY99, 40, 5837.
*a
10% TiCl,(thf), , i-Pr2NEt CHzC12, 25°C
NHPhth
NIIPlth
r__ l
77% (>99: 1 syn:ant4 Yoon, T.P.; Dong, Vy.M.; MacMill an. D.W.C. J . Am. Cliern. SOC., 1999, 121, 9726.
“I-c:l‘
1.lT 80”C, M S SI’hII, , AIBN 5h
2. H Z 0
TrMSS = tns-tiiinethylsilylsilane M Q SI
S02Me
Kizil, M.; Patro, B.; Callaghan, 0.;w
J . Org. Chem., 1999, 64,7856.
v . J.A.; IIursthouse, M.B.; Hibhs, D.
SECTION 344: AMIDE - ESTER
1 . t-BuNC, TIIF I I,CO ,H
@lo)2P(0)c Ph
CfIO
83%
t-BuHN
2. LiBr, N E t 3 , TI-IF
Beck, B.; Magnin-Lachaux, M.; I-Ierdtweck, E.;
87% ph
Org. Lrtt., 2001, 3, 2875.
Section 344
Arnide - Ester
569
NIIPMP
JPMP Ph$iO /==(OTMS OMe
Ph
C02Me
q HBF4 , sodium dodecykulfate
OSiPhl 90% (90 10 syn:unti)
4
Nuvama.,Takaya, J.; Kagoshima, H. Tetrultedron Zztt., 2001, 42, 4025.
0
,,,#’“
M t O H , NaHC03
Me02
COzMe
reflux, 10 inin NHChz h , M e ’ChZ Allevl.;Cighetti, G.; Anatasia, M. Tcrruherlron La., 2001, 42, 5319.
Ly
KN( cycbhexyl)z
Ph-N@OC),
TI IF ,-78°C
88%
C02t-Bu
- A Ph
N(Boch
92%
Kise.;Ozaki, H.; Terui, €1.; Ohya, K.; Ueda, N. Tetrul?erlron k t t . , 2002, 42, 7637. C02Me
TIIF, -78°C
I
N
.y”c
C02Me
-+
0°C
IZIICU(CN)CH~CH~CO~ LiCl M~-~
Ts
C02Me
NHTs 99% Oishi, S.; ‘Tamamura.; Yainashita, M.; Odagaki, Y.; Hlunanaka, N.; Otaka, A.; J . Chem. Soc., Perkin Truns. 1, 2001, 2445. TsNBrNa ,M t C N , rt
Ts,
NrC
cat Pd(Md:N),Cl;! * Antunes, A.M.M.; Marto, S.J.L.; Brunco. P.S.: Prahhakar. S.; Loho, A.M. Chetn. Commun., 2 0 0 1 , 405.
NI I Ac C02Me
112 , Kh (R,R)-MeDuPHS) , i-PiOH
[h~niin]PF6 ionic liquid medium
Guernik, S.;Wolfson, A.; IIrshowitz, M.; Greenspoon, N.; Seresh. S . Chmi. Conintun., 2 0 0 1 , 2314.
60%
NH Ac C02Me quant (99% ee ,R )
v
Compendium of Organic Synthetic Methods, Vol 11
570
P-ToICIIO, EtCN , 3 EtO
-78"C+
TiI4
Section 344
P-ToI
EtO
-20°C
N -Ts
NHTs
. . Shlrmzu.; Takeuchi, Y.;
74% (77:23 anti:syn)
Sahara, T. Chem. Lett., 2001, 1196. ICOzEt 5% PhNMQ, R-Tol-BINAPKuPF6 THF , -78°C
* W J + .
E02c
/
NMe, 75% (96% ee) Angew. Chem. Int. Ed., 2000, 39, 4114.
Saahy, S.; Fang, X.; Gathergood, N.;
1. LDA , TIIF t-BuO
c
rBu J +
Me
NC
A J T n s t r o ;~Atkin, M .A,; Swallow, S. Tc.truherlron .!At., 2000, 41, 2247.
20%
BnOzCHN Zn-Cu , DCM , rt Mecozzi, T.;
NHCOzB n Tetruhedron Lett., 2000, 41, 2709.
82% (28:72 antisyn)
IIZ , P d 4 , EtOAc-EtOH 30 inin
Papageorgiou, E.A.; Gaunt, M.J.; Yu, 1.-q.;
93% Org. k j t t . , 2000, 2, 1049.
Ranu.; Hajra, A.; Jana,
U. J. Org. Chcm., 2000, 65, 6270.
1 . sec-BuLi, TI-IF 2. CuCN.2 LiCl
MtiN-Boc Dieter.
571
h i d e - Ester
Section 344
Me
I
*
C02Me
3. CH2SHC02Me B~~HNLu, K.; Velu, S.E. J. Orx. Chem., 2000, 65, 8715.
u;
@'T
Ph NBS PhCl,refhx,12h , NaOAc , AcOH
*
*2: 85%
0
,Ts
NHTs
SiMq
5 % S-Tol-BINM - C U P F ~ CI r2a2
C02Me
34% (58% ee, R)
Me02
Py Q N H B o c
NaII, THF 1 .
Johnstone, S. .I.Org. Cliiwi., 1999,64,5896. OMe
EtC€I2C02Me, LDA-THF
NI4CO2Me Ti(Oi-Pr)4, -70°C
+
b
xcqN
0
2 C 0 2 M ;
N Hot-B u
76%
2 C Q M . z i-Pr
0°C i-pr NHCOlMe
Kise.;IJede, N. J. Orx. Clieiit., 1999, 64, 7511.
C02Et
H
Fang, X.; Johannsen, M.; Hao, S.; Gathergood, N.; Hazell, K.G.; J. Org. Cheni., 1999,64,4844. Me 0 2 C,,
0
Totruhedron Lett., 1999,40, 8215
Cho, S.-D.; Kim, H.-J.; Ahn, C.;
Et02C
83%
(8
NHC02Me
92) 90%
572
Section 345
Coinpendium of Organic Synthetic Methods, Vol 11
CAN, MeOH
,02
0 0 it, 15inin Nair. V,;Sheeha, V. J. Org. Ch.ern.,IY99,64,6898.
BulSnIi , PhH , AIBN
Benati.
-
k; Nanni, D.;
I;,COCH N
PhH N
-
&
70%
70%
co*Me Snngiorgi, G . ; Spngnolo, P. J. Org. Chenr., 1999, 64, 7836.
CO,t-Bu _ .
-78"C-+ rt Kazmaler.; Zumpe, F.L. Angcw. C h m . Int. Ed., lY99, 38, 1468. ~
74% (96% ds)
Section 315 (Cwhoxylic Acid - h i d e ) Section 316 (Cuhoxylic Acid - Amine) Section 351 (Amine - Ester)
Related Methods:
SECTION 345: AMIDE - ETHER, EPOXIDE, THIOETHER
CI
2 ecl chirul Lewis acid i-Pr,NEt ,-2°C , 1 d
88% (83% ee)
Yoon, T.P.; MacMillan, D.W.C. .I. Am. Cherii. Soc., 2001, 123, 291 1.
H
2
N
e
C
1
0
,toluew
S% Dy(OTf)j ,4"C , 2 d G5% (92:8 endo:em)
Batev. K.A.; Powell, D.A.; Acton, A,; Ouugh, A.J. Tetruliedron Lett., 2001, 42, 7935.
OH
A~nide- Halide
Section 346
573
72%
Yl\ddv.; . . Reddy, B.V.S.;Pandey, S.K.; Siihaii, P.; Prathap, I. Tetruhedron Lett, 2001, 42, 9085.
0
2. Et0I-I ,NEt, ,reflux , 1 h
NHOH 0 CN Boukhris, S . ; Souizi. A . Tetulicdron Lett., 2000, 4 1 , 2559.
Prasad, B.A.B.;Sera, G.;
84~84% OEt
bx
m.V.K. TetrulicJdronLett., 2000, 41, 4677. MeTi(0i-Prh , ?HI;, it
37% (1:3 E:Z)
OBn
C,H,MgBr NB 112 Me Kordes, M.; Winsel, H.; De Meijere. 4.Eur. J. Org. Chenr., 2000, 3235.
A Nb0 A
EtSII , 10% IIf(0Tf)d 0°C 12% chiial oxamlidinone
;.s-
CI12c12, M S 4 A ,15 h
90% (67% ee) Ogawa, C.; Kawainura, M.; Sugiura, M. Synlett, 2000, 983.
-
SECTION 346: AMIDE HALIDE, SULFONATE
N-Ts
ItCl, , M&N , it 8.5 h
b h Y d . S . ; Subha Reddy, B.V.; Kuniar, G.M. Syizlett, 2001, 1417.
N HTs
574
Compendium of Organic Synthetic Methods, Vol 11
Kf
;-
1
.
.
;k'
TIIF, 30% Pd(PPh3)4, fluowscentPPh, light t
I
0
Section 346
0
N
I
TS
Isono, Y.; Iwamatsu, S.-i. J. Org. Cheni., 2001, 66, 315.
78%
Ts
90%
Bu4N (Ph,Si)difluorosilicate Ph
TI-IF , 0°C
NHSOxTol
Ph
L *L
Prakash. G.K.S.; Mandal, M.; Olah. G.A,Synlett, 2001, 77.
1. TsNCl2, MeCN ,r t , 22 h Pd(II)-( 1,lO-phenanthroline)
wC02Me *
Ph
2. 3 NaZSO,
Wei, H.-X.; Kim,S.H.;
Phm C O z M e
C02Me
Ph
1
81% (>95%1anti) Tctruhcdron, 2001, 57, 3869. 1. O-N~SNCIN~, MeCN 10% CU(0Tf)t
2.
COZMe
Ph
Na2S03
74% (>95: 1 anti:syn)
u; Wei, H.-X.; Kim, S.11. ?i,truhcdron, 2001, 57, 8407. 1. p , , W N l i 2
--+
80°C
NHSO 2P hEt
CH2CH2Ph
71%
; Steck, P.L. Eiir. J. Or#. Chem., 2001, 4353.
r
NHNS
. PhH, 18 h
MqAl/toluene , 0°C 2. 4 HCI , 0°C
10 nun
NHTS
I
s0,Ph
84%
Jones, A.D.; Wt.D.W. ; Mihhs, D.E. J. Chenn. Soc., I'erkin Trans. 1, 2001, 1182.
Section 346
A~nide- Hniide
A
+EtOH TMSCI,O°C+& ,1O%F&12 t
575
K
a
0
+&cl
NH
c1 9 ) 72%
(9 1 Dach. T.; Schluimner, B.; Ilarins, K. Clwii. Eur. J., 2001, 7, 2581.
A
Oxone, NaCI ,4S°C Wet N 2 0 , , 4 h
A/
* Ph
I 93% Ac .. UM.; Epifano, F.; Marcotullio, M.C.; Rosnti, 0.;Tsadjout, A. Synlett, 2000, 813. Ph
N HAc
cm,
Li, G.; Wei, 11.-X.; Kim, S.H. Or$. Lett., 2000, 2, 2249.
,
SOzMe
wtBEt,,02 , H 2 0 , 8 h
c
N-!B2Me
I Wakahayashi, K.; Yorirnitsu, €4.;Shinokuho, H.; Bull. Chein. Snc. Jpn.. 2000, 7.3, 2377. PMB
I
T
N
I
Mn2(CO),, , 0.11 M
-
DCM, hv
0
Gilbert, B.C.; Kalz, W.; Lindsay, C.I.; McGrail, P.T.; J. Chein. SOC., Perkin Truns. I , 2000, 1187.
77%
df 0
N
I
76%
PMB ; Whittaker, D.T.E.
Coinpendiuni of Organic Synthetic Methods, Vol 11
576
Section 347
BiCI12C02Et ,In ,THF
PhA N-Bn
8 O C , 12 h
0 Bn A.; Becker, F.F. J. Cheni. Soc., Perkin Truns. 1, 2000, 2179.
-Ghat&,
Rohin, S.; Rousseau. G. Eur. J . Org. Chwz., 2000, 3007. 1 . TsNCI2, MeCN ,MS 4,& 8% ZnC12
-COZMe Ph
2. Ni12S03
COzMe
Ph
85%
U;Wei, H.-X.; Kiln, S.H.; Neighhors, M. Org. Lett., 1999,1, 395.
&
NI-I2
i H T S
r 2O%NaOAc,NBS% ay McCN ,3.5h *
/
Naskar, D.; b v . S. J. Cticvn. Soc., Perkin Truns. 1, 1999,2435.
\ 46%
0
SECTION 347: AMIDE - KETONE
Q
y
1
Do
,reflux
0
M~CIICH2CHzONO
Rayaharapu, D.K.; Majumdw, K.K.; Samhaiah, T.; -P. J. Org. Chem., 2001, 66, 3646.
C.-
Section 347
h i d e - Ketone
0
PhI, K&03 , MeCN 5% Pd(pP11,)~,20 atm CO
c6H 13
90T,6 h
NIITs
* 3
TS
c6H
Kanp.;Kim, K.J. Org. Lett., 2001, 3 , 51 1 . QTIPS
6
577
I. CJI&IIO, MgSOi, It DCM , KZCO, 2. (Et02C)20 , EtOH , rt
Ts 57%
13
3. BF3*OEtz, DTBMP DCM , 0°C (317
72~87% (87% ee) Org. Lett., 2001, 3 , 1229.
Kanetani, A,;
w;
Frantz, D.E.; Soheili, A.; Tillyer, R.; Grahowski, E.J.J.; Reider, P.J. J. Am. Clzem. SOC., 2001, 123, 9696.
Ts s.
77% (26: 1 &ans:cis)
R.W- Satcharoen, V. Synlett, 2001, 532.
-A
10%~(MeCN)zPdCIz, DCM
1.5 t?q ChzNHz , 14 h Gaunt, M.J.;
1
org. L f r t . , 2001, 3, 2s.
NIICbz
84%
Compendium of Organic Synthetic Methods, Vol 11
578
a
MeO
NIITs SnCI, ,DCM , 5 h -78"C+
Section 347
* Me0
rt
73%
Ph . . Sllvelra.; Bemardi, C.R.; Braga, A.L.; Kaufman, T.S. Tetruhedron Lett., 2001, 42, 8947.
Hilgenkamp, R.; &rch er. C.K. Tctruhedrnn, 2001, 57, 8793.
6
1) 70%
(1
Clark.;Hodgson, P.B.; Goldsmith, M.D.; Street, L.J. J. Chem. SOC., Perkin Truns. I, 2001, 3312. PhCII=NTs McOI-I, 40"C, , 2 0 %1DMAP d
@'
50%
Shi.;Xu, Y.-M. Cherti. Cnrrrnrun., 2001, 1876
2.2 eq Bu3SnH ,AIBN toluene, heat
* O~ &sons.
A.F.; Williams, D.A.J. Tctruhcdron, 2000, 56, 7217.
58%
Anide - Ketone
Section 347
579
4Cm
Ti14 , MeCN, 0°C + rt , 22 h
Ph
Ph
MhcN-Bcx %: -
N -Ts . . Shlmlzu.; Sahara, T.; Hayakawa, R. Chein. Lett., 2001, 792.
NHTs
88%
Boc,
,EtzZn *
Me
Br
Br
toluene, 0°C
rt
Me
Paparin, J.-L.; Crkvisy, C.; Gr&. R . Tetruhedron LeJtt.,2U00, 41, 2343.
63% (92% bis-endo)
57% (955) ?MP
v
Alcdide.;Almendros, P.; Salgado, N.K. J. Org. Chetn., 2000, 65, 3310. Boc(Me)NCI-12SnBu3, CuCN
TIIF, 5 eq TMSCl
*
&
f"
N,
'6
; Alexander, C.W.; Nice, L.E. Tetruherlron, 2000, 56, 2767.
Me
98%
1. ' r M S ~ ' " "
Cr(C013
N-BZ
4. 3. 2.'IBAF h v PI1 ,02
\ *,st"\hP '
I
Ishimaru. K.; Kojima, T. J. C I Z P ~Soc., I . Pcrkin Truns. 1, 2000, 2105.
BZ 70% (80% de)
580
Compendium of Organic Synthetic Methods, Vol 11
Section 341
019 1) 92% ,vans P . L . Managan, T.; Rheingold, A.L. J. Am. Cheriz. Soc., 2000, 122, 11009.
* Ph H ZnBq , DCM H B t = benmtiizole 50% Katritzkv. A .R.;Fang, Y.; Silina, A. J . Org. Chcm., 1999, 64, 7622. Ph
Bt
03 OTMS
chiral nitiido-manganese (V)sale11 co1nplex
,,+"NIICOCF,
T F M , Py , E M , 6 h -78°C -., It
83% (75% ee)
Svenstrup, N.;BBgevig, A.; Hawll, R.G.; Joreensen. J. Chein. SOC.,Perkin Trans. 1, lY99, 1559.
I
sp
Ts Wane. .I. Hou, ; Y.; Wu, P. J. Clierri. Soc., Perkin Truns. I, I Y Y 9 , 2277. 1. CIjCCHO, NHzOII*HCI microwaves 2. IIzS04,mianwaves
52%
0
89~75% Janeshwara, G.K.; Bedekar, A.V.; Dcshpande. V.H, Synth. Coinitaim., Z999,29, 3627.
Aniide - Alkene
Section 349
581
SECTION 348: AMIDE - NITRILE NO ADDI'IIONAL EXAMPLES
-
SECTION 349: AMIDE ALKENE
-h. t-Bu
=
Me3Si
1,
O-Li+
[=N-Ts
, THF ,-7X"C 12 h
2. t-BuCIIO, -78°C
+
+
20°C
20°C , 6 h
\
Iwamoto, K.; Kojima, M.; Chatmi, N.; Murai. S . J. 0r.g. Chenz., 2001, 66, 169.
(74
26)
Ts
71%
89%
98:2cis:trur~s ' Jahin. I.; Revial, G.; Monnier-Benoit, N.; Netchita'ilo, P. J. Org. Chem., 2001, 66, 256.
0 N
I
1. f-BuLi 2. MqCu(CN)Li,
3. H 2 0
* W
N
H
T
r
s
71%
Tn Neipp, C.E.; Ilumphrey, J.M.; Martin. S.F. J. Org. Cherri., 2001, 66, 531.
Ph
Ph
. EG.; Trahocchi, A.; Guarna. A. J. Org. Chein., 2001, 66, 2459.
76%
Compendiuni of Organic Synthetic Methods, Vol 11
582
Section 349
-Br
Ph*N-SO,Ph
In
HZO
98% (39:61 syniunti) 95% (79:21 syniunri)
THF/€I,O
Lu, w.;
J. Org. Cheiii,, 2001, 66, 3467.
1. TiCb , DCM -7X"C-r -20°C
CO2Et
Ir
2. KIICO, 83%
Duncan, D.; Llvinphouse. T. .I. Org. Chem., 2001, 66, 5237.
<
C02Me
Balm, D.;
PhCHO , TsNI-I, ,2-propaiol, 1 d* DABCO, 2% La(OTf)-,, MS 4A
..
P
h
0
4C 4 M e 76%
J. Org. chein., 2001, 66, 6498.
/T" SIBUS
, 8% Pdz(dba)-,
14% AsPh3,S eq CUCI nw, SOT
83%
Minisre, S.; Cintrat. J.-C. J. O q . Clzeni., 2001, 66, 7385. Ts
I
10% Gmbhs' catalyst , DCM
ON\
1'"
CH2=CI12,rt , 1 d
Kitamura, T.; MQLM. Org. LEtt., 2001, 3, 1161.
56%
b i d e - Alkene
Section 349
583
Ph
+ BU
1) 87%
(3 Greig, I.K.;Tozer.;Wright, P.T. 0r.g. Lett., 2001, 3, 369.
EtOzCCIIzCN, bluene , 80°C at Rhj(C0),2,4 h
85%
Takaya, H.; Kojima, S.;
Org. Lett., 2001, 3, 421.
Solin, N.; Narayan, S.; Szahb, K.J. 0r.g. Lett., 2001, 3, 909.
i-hA/"'a
ug
1.2.2q 2. ClC02Ph 3. Gruhhd catalyst DCM, retlux
W E ;Aponick, A. Org. Lztt., 2001, 3, 1327. PhN=C=O 5 % Cp*Ru(u>d)Cl I X E , reflux , 1 h
Yamamoto, Y.; Takagishi, €1.;
*
c)
i-Pr
Ts
65%
I
80~98%
an
0r.g. Lett., 2001, 3, 2117
CqPh
0
62%
584
Compendium of Organic Synthetic Methods, Vol 11
1.5R NEt, U ~ ( C O ) ~ ~c cat
I.&
4
Section 349
1
b
x
dioxane , 9 h 85% NTs Ts 0 20 atm CO S.-IG, Kim, K.-J.; Yu, C.-M.; IIwang, J.-W.; Do, Y.-K. Org. Lett., 2001, 3, 2851.
BOG
Green, M.P.; Prodger, .I. Sherlock, ; A.E.; fI;lves. C.J, Org. k t t . , 2001, 3, 3377.
0
97% (98 : 2syn:anti)
0
Dong, V.M.; MacMillan, D.W.C. J . Ant. Cl?t~n.Soc., 2001, 123, 2448. 1. C3I171.2.5 eq S11112,THF l%Ni12, 20°C. 10 nun
cd17
I
2. 0.5 M HCl Me Farcas, S.; JVamv. J.4, Tetruherlron Ln.tt., 2001, 42, 879.
/Ts
In ,MLOH , i ~ f l u x, 4 h CXH17
95%
Me
NHTs
A/
. , v. J.S.;Bandyopadhyay, A; Reddy, B.V.S.Synlett, 2001, 1608.
95%
Section 349
585
h i d e - Alkene
Br
ZnClz , Na2C03, 95°C , 1 d
w;Ramesh, C.; Kulkarni, G.M. Sywlett, 2001, 1241.
A
ALO
N--Ts
SiMe3
53%
Ph
b f l
, 'IFIF, 65°C
10% [(Pd(OAc)2/P(0i-Pr)3/BuLi/tohene]
I
82%
IIedley, S.J.; Moran, W.J.; Prenzel, A.H.G.P.; Price, D.A.;
Ts
Synlett, 2001, 1596.
cj-fC1doM MeOLi, MtOII
N
0
I
0°C ,2.5 h
0
I
OMe
Bz 62% Bz Bellesia, F.; De Buyck, L.; Colucci, M.V.; melfi. F. ; Laureyn, I.; Lihertini, E.; Mucci, A,; Pagnoni, U.M.; Pinetti, A.; Rogge, T.M.; Stevens. C.V. Tetruhedron LEtt., 2001, 42, 4573. NIII3oc
I
n
hssM:u.tin periodinane
Yu, C.; Nu. L. Totruheciran Iltt., 2001, 42, 5167
T"I
"" NI-lTs
Te-', I120hluene /
Chao, B.;
m.D.C. T~~tlalic~drori LJtt.,2001, 42, 5789.
92%
I
Compendium of Organic Synthetic Methods, Vol 11
586
89%
5% Pd(PPh&, toluene 10%P(0)Ph3 ,20"C, 16 h
Bu
Oh, B.H.; Nakamura, I.; Saito, S.;
Kiewel, K.; Tallant, M.;
Section 349
Ts
Tetruhedron Lett., 2001, 42, 6203.
Tetruherlron Lett., 2001, 42, 6621.
Arisawa, M.; Theeraladanon, C.; Nishida, A.;
TetruhedronLett., 2001, 42, 8029.
Akila, S.;Selvi, S.; Balasuhramanian. K. Tefruhcdron, 2001, 57, 3465.
Cl
mBr ,MeCN Me
cat P d ( C l z ( M ~ c N h K2cO3 , 7 5 " C , 1 h
0 Karstens, W.F.J.; Klomp, D.; Rutjes, F.P.J.T.;J-Iiemstra. 11. Terrulzerlron, 2001, 57, 5123.
phz 587
Amide - Alkene
Section 349
N€ICOzMe
hlf
Na2C03t
2. KOH , NazS04
Ph
1) 70% Tefruhedron, 2001, 57,8257.
(1
Kim, J.D.; Lee, M.11.; €Ian, G.; Park, 1-1.; Zee, O.P.;
R
Me
P hCI-€,O€I
ehz'
(1,lO-phenimtro1ine)NiClz PhCl , NaI-I ,rt Y . 4 , Syntlz. Corrirnun., 2001, 31, 1201.
Ren, €I.-J.;
80%
MeO,C\
2 y C 0 , MeOH ,0.5 NHz
cat PdIz , KI,
0 2
70°C , 15 h
&
H 53% Gahriele. B,; Salenio, G.; Veltri, L.; Costa, M.;Massera, C. Eur. J. Org. Chem., 2001, 4607.
a& I
Ts
;-
Bn
CHz=C=CIIz , KzC03,
NHBn
cat Pd complex
54%
Kijppen, I.; Rasparini, M.; Sridh;iran, V. Chcrrl. Comritun., 2001, 964.
SIllI,, 25°C
Ph
b
C1
Ph
TS
90%
Concell6n. J.M.; Pkrez-AndrGs,J.A.; Rodriguez-Solla, 11. Cherii. Eur. J, 2001, 7, 3062.
588
Coinpendiuin of Organic Synthetic Methods, Vol 11
&
PhMgBr
N\ N IITS
I
Section 349
TIIF, reflux
Lr
NIIEk,
l'h 75%
Br2 Chandrasekhnr.; Reddy, M.V.; Rajaiah, G. Tefrukedron Left.,2000, 41, 10131.
12fCH0
Pd(OAc), , ALOH Bn-
N
I
LiBr Xie, X.;
Bn
87% (>98:2 Z:E)
Synlett, 2000, 707.
PhM
'
Berger, D.;
J3
N
cat Ru3(CO),, ,
CH2=CII2
co 93%
Tctruherlron,2000, 56, 2015. OTMS
Ph*N
1. Cp,ZiC12 , 2 eq BuLi THF,-7X"C+ It
2. EtCIIO
P h-N
H 52% (85:15 E:Z)
Gandon, V.; Bertus, P.;
Me
.. .
m u .
=
Tetruhedron,2000, 56, 4467.
*
OLi
r NOMe
PI1
TIIF, rt, 12 h
88% (>99:1E:Z) IT,; Oya, S.; Murilkami, R.; Sntoo, Y.; Shishido, K. Tetruhedron Left., 2000, 41, 5947.
Section 349
589
Aniide - Alkene
MeO+OMeM e 0
1 . BuLi , LiCl , THF ,-78°C
p i-Pr
67% (67%ee)
3. HCI, rim, OT IIarrington, P.E.; Tius. M.A. Org. Lztt., 2000, 2, 2447.
Bz"-P I
-
LDA ,TIIF-IIMPA
Bn
SiMe,Ph
Anderson.;Flaherty,
-78°C
-f
SiMe,Ph
40°C
84% (20: 1 ) A.; Swarhrick, M.E. J. O r g . Chent., 2000, 65, 9152.
\
* yLj(O?'f)3, air, TIIF
+
-J (65
Porter. N.A.; Zhang, G.; Reed, A.D. Tetruhedr-onLftt., 2000, 41, 5773.
35) 82%
\
w;
Bn
89%
I'retwell, P.; Sansuno, J.M.; Sridharan, V.; Sukirthalingm. S.; Wilson, 11.; Redpath, J . Tetruhrrlron, 2000, 56, 7525.
Section 349
Compendium of Organic Synthetic Methods, Vol 11
590
4 eq MeCu(CN)Li=LiBi*2 Li
I
MTS
Me
MTS = 2,4,6-timethyhenzenesulfonyl
93% Ohno, H.; Toda, A.; Miwa, Y.; Taga, T.; Fujii, N.; Ihuka. T. Tetruhedron Len.,1999, 40, 349.
&\J
u Lh
do [Pd(MeCN),I[BFJ,, CH2CI2,72 h
fi
Ar,
71% (83% ee)
AI = 4-CF3 phellyl Jiang, Y.; Longmire, J.M.; 7,hane. y Teriohedron Left., ZYYY, 40, 1449.
r-BuMqSiCl195"C111 12 h C O , RhZ(C0)12, Ph€I
B-u
4rD SiMe,t-Bu
* Bu
pyrrolidine
90% (9?:3 Z E )
0
Matsuda. I.; Takeuchi, K.; Itoh, K. Tetruhodron Lett., ZYYY, 40, 2553
A
r
-
5% Pd feimcenyl oxazoline CH~C12,23"C, 3 d
3
C3H7
.
Donde, Y.;
J. Ain. Cheiil. SOC.,ZYYY, 121, 2033.
67% (91% e e , R)
1. (-)-sparteine, BuLi toluene, 1 h
N &'
\B<,c2.
EtOzC
&COZfi
Ar = 4-OMe-C6II,
C0,F.t
Curtis, M.D.; &&J J. Or#. Chein., 1999, 64,2996.
Ph 93%
NArBoc
59 1
k n i d e - Alkene
Section 349
7== +qh 1. In , 'IIIF reflux , 18 h
2. Dcc ,cat. 4-PPY CH,CI, , 3 0 inin, rt
Br
O* 4 P P Y = 4-pyirolidinopyridiiie Choudhury, P.K.; Fouhclo, F.; Xui-.M. J. Org. Cfiem., I999,64,3376.
MelSi
\
83%
H
Ph
otx. Lett., 1999,I, 641.
Bennett, D.M.; Okainoto, I.; TsIIN Pd(PI'h3h9 K2C03 PhI, D M F , 80°C 40 h
A
Ph
Me
*wx) Ph
\
I
TS
Ts
(10 : W) 34% Rutjes, F.P.J.T.; Tjen, K.C.M.F.; Wolf, L.B.; Karstens, W.F.J.; Schoemaker, H E . ; Hiemstra. 1l, Org. Ixtt., 1999, I, 717.
-,-
ph---='Z
B I I N I I ~toluelle , , 110°C , 2 h
'
I
C O Z ( ~ k 5
PhT 82%
0
SuPihara. T.; Okada, Y.; Yaniaruchi. M.; Nishizawa, M. Synlett, 1999,768.
1 . 3 eqTMF t-BuLi , -78°C: , 6 e q,IIMPA 16 h
G 1 - t - B .
2. NHdCl
Ahmed, A.;
I ; Yasin, S.A. Clierrz. Coumim., 1999,231.
75%
Ph
Section 350
Coinpendiuin of Organic Synthetic Methods, Vol 11
592
REVIEWS: "1,3-Diplar Cycloadditions of Five- and Six-Memhered Cyclic Nilrones to a,p-Unsaturated Acid Derivatives," de Marc$J; Figueredo, M.; Font, J. Heterocycles, 1999, 59, 1213. Also via Alkenyl Acids: Section 322 (Carhoxylic Acid -Alkene)
-
SECTION 350: AMINE AMINE
1 . Yh , TIIF-IIMPA, r t , 2 h
Ph-N-Ph
*
2.1-Np-CIIO, 1 2 . 2 h
Ph-N
aNo2 a? aN a,)
Ph Jin, W.; Makioka, Y.; Kitamua, T.; Fuiiwura. Y. J . Org. Clwrrt., 2001, 66, 514.
N3
1 . ITiCl,/S1n/T1IF/~fluxRh] TI-IF , rt , 5-10 inin
,THF ,60"C , 2 h
2'
w Chen, ; X. Tctruhetlron Lett., 2001, 42, 73. 0
Zhang, W.;
H
78%
MglMeOH , 60°C
*
86%
PTdShdd.; ,. . Liu, Y.; RepiE, 0. Tctruhcdron Letf., 2001, 42, 2277. N-oMe
/L
Yh
I1
Zn*TiC14, TIIF
N H2
qfi
Ph
Kise.;Ueda, N.Tetruhcdron In)tt., 2001, 4 2 , 2365.
Nil2
76% (60:40 &:meso)
Section 350
Amine - Amine
MqSi2NH, NaH , Li ,ether
PhCIIO
593
’u
*
Ph
5M LiC104/ether, ultmsund , 5 h
NI12
Fh 42% ( m 2 4 meso:d)
Mojtahedi, M.M.;&&JLF.L ; Shirzi, J.S.; Bolourtchian, M. Synth. Commun., 2001, 31. 3587.
hfPh NBt,
v i I 4 , 2eqZ111, T I I F , 3 h
+OEt
* Ph
NEt2
Cl1en1. LPtt., 2001, 1334.
Yoshimura, N.;
1
CpzTiFz, I’hMeSiI12, toluene
Ph
~
it , 30 min
5 Ph
95% (4555 dkmeso)
NEt,
P
h
N Me2 Selvakumar, K.; Hanod. J.I7 Angew. Clierii. Int. Ed., 2001, 40, 2129.
84% (52:48 meso:dl)
NIIt-B u
5) 84%
(05
Chung, T.-11.; Sharnless. K.B. Org. IAtr., 2000,2, 3555. PhA N-t-Bu
hv , Pyrex , 3 h i-PdIIi , acetone
t-BuHN
Ph
NI-It-BU t-BuHN B
Ph Ph (45 Camnos. P.J.; Arranz, J.; Rodriguez, M.A. Tetrahedron, 2000, 56,7285.
Ph
55) >95%
Section 350
Compendium of Organic Synthetic Methods, Vol 11
594
fh phHc=T 0-
In , EtOH , reflux
P h y (
12 h
NAPh
99%
NHPh Jeevanandm, A.; Cartwright, C.; h i e . Y .-C. Synth. Coninirtn., 2000, 30, 3153. PhNHMe ,Sn(OTf), 10 inin
m.V.K. J. 01-g.Clicjni., ZYYY, 64,2537.
MqN
Sekar, G.;
Rh chird diamine compkx
IICOOII , NEt, , MeCN
MIS
Mao, J.; &&L.
M*
96% (89%ee) Me
Mr? D.C. 0 r g . k t r . , IYYY, I, 841.
+Me$ Cn’i(Oi-Pr), , THF ,rt c-C, IkMgCl Ph
Bn
(72 Cao, B.; Xiao, D.; Joullie. M.M. Org. Lxtt., ZYYY, I, 1799.
Ph
Bn 28) 83%
I ,
1-hroinonaphthalene , t-BuONa
TIIF Pd2(dha)~/dppf, b t . C.G.; Mendoyo, P. l’ctruherlron Asynint., 1999, 10, 1831.
NH(1-naphthyl)
Section 351
Amine - Ester
595
-
SECTION 351: AMINE ESTER C02Me
PhzNII, catRhz(OAc)4 PhII, 1 h
.2==(
C02Me Yang, M.; Wang, X.; Li, €1.;
>\
.-
P
I
84%
d
C0,t-B u
Ph
ph>YCO~t-Bu
Triton-X - 1 00
Bn
92% (85%ee)
Okino, T.; Takernoto. Y, Org. k t t . , 2001, 3, 1515.
ph>N Ph
z
COzMe
1% chiral ammonium salt 2.4 eq BnBr , ay KOII ,rt*
C02t-BU
h
J. Org. Chetn., 2001, 66, 6129.
Ph Ph
COzMe
moAc, 3h
* p h ) = = N P m
[(pd((%Hs)C1lz P(OPh)3 Ph COZ-Bu chiral phase transfer catalyst 50% aq KOH , toluene. 0°C 89% (96% ee) Nakoji, M.; Kanayama, T.; Okino, T.; Takernoto. Y, Org. Lett., 2001, 3, 3329. 1
1. BnBr , KOH, TBAB Soxhlet
Ph
2. H+ 3. AcCl , MeOII 4. IIN=CPh2 Kim, H.J.; Lee, S.-k.; Park. Y.S. Synlett, 2001, 613.
€I
Bn
Ph
3% Cinchona alkaloid ,Me1 Ph
COZt-BU50% KOH , tolueneCHC1, -2O"C, 1 d
68:32 (S:R)
* Ph
Me
Park.;Jeong, B.-s.; Yoo, M.-s.; Park, M.-k.; Huh, €1.;kw. S.-& Tetruhedron Lett., 2001, 42, 4645.
Kita, Y.; Maekawa, H.; Yamasaki, Y.;
'
Ph
Tetruhedron, 2001, 57, 2095
(9O%w,S)
Compendium of Organic Synthetic Methods, Vol 11
596
OlMS
, AlCI, ,17h
MS 4A ,DCM ,-78°C
-
NHPAN 0 rt
69%
. . Shlrnlzu., Ogawa, T.; Nishi, T. Tetruhedron Lxtt., 2001, 42, 5463. COzMe
Section 351
C0,Me
NEt, , toluene ,refhx
96%
EtzN Tetruhedron L.ctt., 2001, 42, 8387. 10% c h i d phase transfer catalyst, 50% aq KOH
phTN> Ph
CO,?-Bu
DCM BnBr
*PhyNym7:i:86%
ee)
Bn Lyeo. B.; Croshy, J.; Lowden, T.R.;Peterson, J.A.; Wainwright, P.G. Terruhedron, 2001, 57, 2403. Ph
9
NHFh
1. PhNHTMS , 5M LiClO,/ether 2. BrZnCH,CO,Et 3. H,O Saidi. M .R.; Azizi, N.; Zali-Boinee, H. Tetruhedron, 2001, 57, 6829. Bn 1. SnC14
51%
2. NZCAC0,Et
BnN ’HBn Bn la.; Choi, H.G.; Park, C.S.; Chang, J.W.; Lee. W . L ; Lee, K.-D.; Suh, J.-M.; Park, J.-H.; I Dong, Y.; Yun, H. Tetruhedron, 2001, 57, 8267.
TMSNHOTMS , DCM
””-””)-(””’
73% (76% ee)
m2Me i-Pr COzMe cat Cu(his-oxawline) , -10°C i-pr Cardillo. G.; Gentilucci, L.; Gianotti, M.; Kim, H.; Perciaccante, R.; Tolornelli, A. Tetruhedron Asynim., 2001, 12, 2395.
Section 351
Amine - Ester
597
/ I s
C0,M
A
NEt3 , PhII
S
80%
COzMe
M r . A.S.; Akhmedov, i.M.; $qieno3u, 0.;Alptiirk, 0.;Apaydun, S.; GerGek, Z.; Ihrahimzade, N. J. Chem. Soc., Perkin Trunr. I, 2001, 1162.
/vCo2Et t-BuI , BEt3 , O z , DCM
BnO
85 %
B F3-OEt, COzEt Halland, N.; Jargensen, K.A. J. Chem. Soc., Perkin Truns. I , 2001, 1290.
a z t - B u EtI, 50% , -20°C 5% c h i d Cinchona alkaloid Ph kw.
toluene-CIICI3, 10 h
s.-&; Jeong, B.-S.; Yoo, M.-S.; Huh, 11.;
Hip"
ph
L N - p - An
1
"YNv --
CO+-Bu
*
Ph
- ?
iit
50% (92%ee) Chem. Commun., 2001, 1244. NHp- An
, Amberlyst 15-DRY
EtOH ,it
Ph
himizu. hl_; Itohara, S.; Hase, E. Chem. Conmmim, 2001, 2318. .
-
.
83%
, toluene
PhA
N
OH
cat [ZifO i- R)4/i-ROWS-VAFQL - NMI] -45"C, 20 h
C02Me
92% (91%ee) Xue, S.; Yu, S.; Deng, Y.; !KuE W.D,Angew. Chem. Int. Ed., 2001, 40, 2271.
K
N.-OBn
MeOzC
€I
5 q i-R-I,S q BEt3
25°C. DCM, cat N B N
C0,Me
*A
i- k
Miyahe, 11.; Ueda, M.; Yoshioka, N.; Yamakawa, K.;
65%
C0,Me
N HOB n
+-
Et
NIIOBn 17% Tetruhedron, 2000, 56, 241.
598
Compendium of Organic Synthetic Methods, Vol 11
Section 35 1
1. 1% chiral phase
Ooi, T.; Kameda, M.; Tannai, 11.; Maruoka.
Wo HN
Tetruhedron Lett., 2000, 41, 8339.
MLO~CCHO, InCb ,TsOH
c1
, MgS04
.'QNH2
76%
DCM , reflux
c1
Huang, T.; Li. C.-.I. Tetruherlron Lett., 2000, 41, 9747. 0 II
MeO'F-
CHO
H
* +OMe
Me0
NMe,
37%
MeONdMeOII
NMt.3 Bulev. A.Yu.; Larina, L.I.; Voronkov, M.G. Tetruhedron Lett., 2000, 41, 10211.
N-OBn El ,BEt, ,toluene 20°C
(TTBDPS
Miyahe, H.; Fujii, K.; Goto, T.;
Q0 \
OTBDB
(18
aOrg. Lett., 2000, 2, 4071. 2 ~ B u N HDMF ~ , 5h
OTf
de Saint-Fuscien, C.; Tarrade, A.; Dauhan, P.;
*
:
1) 53%
OTBDPS
Po 55%
Bn
Tetruhedron Lett., 2000, 41, 6393.
-"
Section 35 1
A
Ph
Arnine - Ester
599
1. NaOH ,BnBr , Cu-salen complex bluene , 18 h COzMe
Xco2= Bn
I ,
2. MeOH, AcCl , toluene, rt 3. silica gel
H P
91% (81% ee) Belokon', Y.N.; Davies, R.G.; North. M. Tetruhedron k t t . , 2000, 41, 7245. 2
EWHz , HzO
CO2Et
75%
COzEt
Stefanl.;Costa, I.M.; Silva, D.de 0. Synthesis, 2000, 1526.
E'02uca" , Mn02
QN+ 0 b C 0 2 H
-
toluene, NEt, ,90"C , 2 h
c1
92%
Zhang, L.; Liang, F.; Sun, L.; Fu. Y.; Hu, H. Synthesis, 2000, 1733.
P+ -
-\ Ph
P h H Y
oms
*I
4 O T M S , 10% La(OTQ3 OEt
*m -<
DCM,4h
Oian.;Wang, L. Tetruhedron, 2000, 56, 7193.
97%
COzEt
COzEt
&
Bae, J.W.; Cho, Y.J.; Lee, S.H.; Yoon, C.-O.M.;
P
h
4
B I C H ~ C O Z MNZ ~ , ,rt
t
89%
ZnCu/MZClz, 1 h COzMe ~
~~
Adrian Jr.. J.C.; Barkin, J.L.; Hassih, L. Tetruhedron Zxtt., I Y Y Y , 40, 2457.
600
Compendium of Organic Synthetic Methods, Vol 11
/ C O z M e
+
0 I
Section 351
hv (350 nm) , MeCN snsitizer
N
I
Me
87% Me sensi tizer = 4,4'-dimethoxybenz~phenone Bertand, S.; Glapski, C.; m a n n . N .; Pete, J.-P. Tetruhedron Lett., 1999, 40, 3169.
-" PI1)IN Ph
3.5 eq CsOH/HzO, Me1 Ru-polypyridyl complex
Tzalis, D.;
Ph
-"
LCO,~-I]~ CH&I2, -78"C, 7 h
A
* P h%>NF
toluene, solid KOH
(Qi-Pr
C02t-Bu
Me
Tetruhedron k i t . , 1999, 40, 3685. CU(.den) complex , BnBr
82%
*
Ph
YPh 4%
CQi-Pr
40%(85% e e , R) M.; Kuhlitski, V.S.; Ikonnikov, N.S.; Kraskik, P.E.; Maleev, V.I. Tetruhedron k t t . , 1999, 40, 6105.
Belokon. Y.W, North,
99%
Larksarp., C.; Alper. H. Org. Lett., 1999, 1, 1619.
%IJuhl, K.; IIazell, R.G.;
Ph*N-Ph Ifayakawa, R.;
BF4-
CIlCl, , 60°C, 34 h
J. Chcni. Soc., Pcrkin Truns. 1, 1999, 2293.
OSiMe, SmI3 , EtCN
Cliein. Lett., 1999, 591.
COZEt
Section 352
Amine - Ether
601
Section 315 (Carboxylic Acid - h i d e ) Section 316 (Carhoxylic Acid - Amine) Section 344 ( h i d e - Ester)
Related Methods:
&
SECTION 352: AMINE - ETHER, EPOXIDE, THIOETHER
0
,InC13 ,EM-toluene h
/”
Ph
Kr2tlI
+
9 /
, Tick
ID
I1
rt,6h
/
Ph
(1 14%ee Sundararaian. G.; Prahagaran, N.; Varghese, B. Org. Lett., 2001, 3, 1973.
MeCN ,It, 15 min PhCI I=N- P h , B i ( 3 3
-
ff
0.67) 70% 5% ee
) 95%
%Ph
..a
lallll
30 7
%/,/,
Dh Reddy, B.V.S.; Srinivas, R.; Yadav, J.S.; Ramalingam, T. Synth. Cotnmun., 2001, 31, 1075.
(CIIO), ,Bu,NH, neat
CuI/A1203, microwaves
G.W.; Wang, L.; Pagni, R.M. Tctruherlron Lett., 2001, 42, 6049.
OH
LiBF, , MeCN , rt ,2.5 h 90%
Yadav. J.S.; Reddy, B.V.S.; Madhuri, Ch.; Sahitha, G.; Jagannadh, B.; Kumar, S.K.; Kunwar, A.C. Tetruhedron Lett., 2001, 42, 63x1.
Compendium of Organic Synthetic Methods, Vol 11
602
,heat, PhH
Ph,CS-NO
A
Ph
Section 352
*
E S C P h 3 Ph Cavero, M.; Motherwell.;Potier, P. Tetruhedron Lett., 2001, 42, 4377. i-PIOH
0
Cheng, X.;
pyrroldinone , K2Pd(SCN)4 70"C, 16 h Tetruhedron, 2001, 57, 5445. PhSII ,5% ZnClz , DCM
,,,''\+fi
Wu, J.; &uJJ.
-
*
ph',\t'"
82%
SPh
&:
; Dai, L.-X. J. Chem. Soc., Perkin Truns. 1, 2001, 1314.
/UuCN
e- , LiQO, , DMF
Ph
*
Br
Batanero, B.; Vago, M.; Bi&i,L
NC
C02Me 1. T i c 4 , DIPEA ,-80°C 2. PhCH=NAr , DCM ,-80°C 3.1MHCI
= P
5
Tetruhedron Lett., 2000,41, 3389.
-
NIIAr h
y
C02Me
C02Me
-k Ph
OMe
OMe Ar = 2-chlorophenyl
67%
Heterocycles, 2000, 53, 1337
Nishitani, T.; Shiraishi, H.; Sakaguchi, S.;
OMe
Na qfi 52%
/Bn P h"'
72%
(93
7)
Jr.. J.C.; Barkin, J.L.; Fox, R.J.; Chick, J.E.; Hunter, AD.; Nicklow, R.A. J. Org. Chem., 2000, 65, 6264.
83%
Section 353
Amine - Halide
603
Ni-Pr 1.MeOH,heat,2 h
2.
c1
K2C4
"'"'Me NHi-Pr
89~91%
OTMS Aelterman, W.; De Geyter, K.; De Clercq, J.-P. J. Org. Chem., 1999, 64, 5138.
;-
1 . 2 eq PhSSPh, DCM 1.Sq TEMPO, i-Pr2NEt
2.
(==$sea
75%
cl Lin, X.; Stien, D.; Weinreh. S.M. Org. Lett., 1999, 1, 637.
REVIEWS: "2-hninothiophenes by the Gewald Reaction," J. Heterocyclic Chetn., 1999, 36, 333.
;Rangnekar, D.W.; Sonawane, N.D.
SECTION 353: AMINE - HALIDE, SULFONATE
Tsuritani, T.; Shinokubo, H.;
1. t-Bu02CNBr2, DCE, reflux
A
Ph
Klepacz, A.;
Org. Lett., 2001, 3, 2709.
2.12% N a 2 S 4 , l O " C 3. HCIDCE , 0°C + fl '
-
Tetruhedron Lxtt., 2001, 42, 4539.
C1
I
N\ Bu
L N H 2 - H C l Ph 83%
10% Sn112,TtIF/PhI1
S O T , 12 h
.. . Gottllch.; Noack, M. Tetmhedron Lrtt., 2001, 42, 7771.
54%
Compendium of Organic Synthetic Methods, Vol 11
604
c1
1. CuCI , T H F , 5OoC, 12 h
I
.. .
c
2. cow. NH3 , H2O
Bu
N \-
Section 354
Synthesis, 2000, 1526.
a-,
TiC13-BF3,-78°C deoxygenated DCM
Bu-
t-Bu
Hemmerling, M.; Sjoholm,
(13 1) 93% Tetruhedron Asynlnt., 1999, 10, 4091.
A.;
SECTION 354: AMINE - KETONE
mu \
Me Bennasar.;Roca, T.; Griera, R.; Bosch, J. J. Org. Chciii., 2001, 66, 7547.
++A
Bartoll.;Bosco, M.;
Bn2NH, c&13-7 HzO, NaI SO,, 4 5 h '
; Petrini, M.; Siunhri,
J. Org. Chem., 2001, 66, 9052.
(k
*
45%
91%
L.; Torregiani, E.
H z N o O M e , acetone
P hff I 0
DMSO,rt, 1d,20%
N H
COzII
Notz, W.; Sakthivel, K.; Bui, T.; Zhong, G.; Barhas
Ph 45% (86% ee)
IIX, C.F. Tetrahedron Lett., 2001, 42, 199.
Section 354
+
Amine - Ketone
a,,,
PhCHZNPh, Yh(OTf),
605
NIWh
TMSQ , T H F , r t , I d * ‘XHl7 CX% NHPh Kakuuchi, A.; m u c h i . T.: Ifanzawa. Y,Tetruhedron Lett., 2001, 42, 1547.
\
\
PhCOC1,Si02,4min micwwaves
*
Bz
. -
Sadeghi, M.M.; Safari, 1.; Minaeifar, A. Tetruherlron Ixtt., 2001, 42, 4363.
;-
I
63 %
2. BF3*OEtz 3. 15% HCI in acebne
-
Cihlat, S.; Canet, J.-L.; Troin..Tetruherlron Lett., 2001, 42, 4815.
-0
70%
a. LoMe
yadav. J.S.; Ahraham, S.; Reddy, B.V.S.;Sahitha, G. Tetruliedron L.ett., 2001, 42, 8063.
PhCN
, .
(&u.
1. Et3BHLi, TIIF, rt
*‘
*
,rt , 5 h
90%
Ph
Synthesis, 2001, 828
S.-S.P,; Hung, C.C. Synth. Conwun., 2001, 31, 1007.
606
Compendium of Organic Synthetic Methods, Vol 11
Section 354
2. p-TSA ,toluene ,heat 3. rI+ , acetone
H2N
0 Glasson, S.R.; Canet, J.-L.;
AN/... \
Ph
49%0verall
Tetruhedron Lett., 2000, 41, 9797.
1. CH2=CIIMgBr1THF , rt * Phi i / \ , , O M e 2. H2O
Me G o r n t u Org. Lttt., 2000, 2, 11.
I
77% Me
n
c3H7 I,
NH
Ph
Sklenicka, H.M.; Org. L.ett., 2000, 2, 1161.
1
Ph
EtOAc ,toluene, 2 d 150"C, sealed tube ,,@\ 64% (75:25) Me Ph ; Wei, L.-L.; McLaughlin, M.J.; Gerasyuto, A.I.; Degin, S.J.
HNEt2 , I-ICIIO, EtOH , 10 mi11
*
m i m w aves
Gadhwal, S.; Baruah, M.; Prajapati, D.;
I
PhLNEt2
60%
Synlett, 2000, 341.
OMe
CU@Sk, H20,O"C Kohavashi. S.; Ueno, M.; Suzuki, R.; Ishitani, H.; Kim, IL-S.; Wataya, Y . J. Org. Chem., 1999, 64, 6833.
65 %
Section 354
mAC
Amine - Ketone
a
607
1. EtzAlCI , DCM , 0°C
2.AcCl ,DCM,O"C
I1
86%
*
Okauchi. T,; Itonaga, M.; Minami, T.; Owa, T.; Kitoh, K.; Yoshino. Org. Lett., 2000, 2, 1485.
L
M~O-
Ph
N E ~ , , La(0Tfh-n II,O
* Ph+NEtz
a chiral bis-naphthoxide
. ..
Yamasaki, S.; Iida, T.;
#
53% (30% ee)
Tetruhedron Lt.tt., 1999, 40,307.
1. 2 CII,=NMe,+ CT CIIzClz, -30"C, 5 h P
2. HCl Arend, M.;
H
fL
h
70%
v NMe,
Tetruheclron Lett., 1999, 40, 6205.
PhNIIz, THF , 0°C Bu,SnClH-IIMPA, Suwa, T.; Shihata, I.; Nishino, K.;
2h
5%
Bz
Org. Lett., 1999, 1, 1579.
acetophenone, PhNH, , 2 3 " C , 12 h
NHPh
0
P hCI 1 0 10% dodecylhenzenesulfonic acid in water Manahe, K.; Kohav. ashi. S.Org. k t t . , 1999, I, 1965. +')TMs PhA N - P h
Ph
,0.1 HBF4
phu
p
NHPh
aq MeOII, 30 min * PhuPh M y r n a . T.; Takaya, J.; Kegishima, €1. Synbtt, 1999, 1045.
h
"%
0
96%
GO8
Compendium of Organic Synthetic Methods, Vol 11
A N-Ph Ph
Aklvama.;Takaya, J.; Kagoshima, H.
0
HZO , 0°C
Chem. Lett., 1999, 947.
MeNI-I:!, NEt3 , McCN ,rt
OII
NHPh
4 O T M S , PhCHO , MeCN Ph
2 qBF,*OEt,, 10
Section 355
s
-
-
97%
moE
0 84% F m k a w a . 1.; Fujisawa, H.; Ahe, T.; Ohta, T. Synth. Continun., 1999, 29, 599.
NHMe
OMe
I
20% HCI
dioxane
-
OH & . . &.iDoi, dM.; ;Shimizu, If.; Etoh, H. Heterocycles, 1999, 51, 2415.
-
SECTION 355: AMINE NITRILE
/"" Kumar, K.A.;
-
1. Chloramihe-T*3 H 2 0 , dark , 8 h
AgN03 ,TIlF,
d c N 4 2 x 5 6 %
2. NaOH , TIIF, 3 h sealed tube, reflux 4CN ; Umesha, K.B. Tctrulzeclron, 2001, 57, 6993.
A O w N F i
82%
clay, EDC , reflux Shaikh, N.S.;
.B .
~
d Tetruhedron, u 2001, 57, 9045.
Section 355
609
Amine - Nitrile
-0CqMe
, toluene
TMSN, ,cat P~l~(dha)~.CHCl, dppe , C O T , 1 h * OMe
2 Ma 99%
Karnijo, S.; Jin, T.; Yamamoto. Y. J. Ant .Clzent. Soc., 2001, 123, 9453.
d>
*'
,HzO
/
cH2(CNh
\
CN
ce tyltrine thylammonium 0 2 b chloride
. . Balllnl.; Bosica,
G.; Conforti, M.L.; Maggi, R.; Mazzacani, A,; Righi, P.; Sartori, G.
Tctruliedron, 2001, 57, 1395.
1. 10% SC(R-BINOL)~L~ ,TMSCN
*
toluene, -2O"C, 9 11 ph>N-Bn
F%qNIl13n
2. H20
>95% (88% ee) Chavarot, M.; Byrne, J.J.; Chavant, P.Y.; VallCe. Y, Tetruhcdron Asymm., 2001, 12, 1147.
0m
F%
/J
Bu,SnCN, 0.1 ZifOt-Bu), 0.3 R-6-Br-BINOL , 12 h toluene , PhH, -65°C
-
0°C
1
92%(91%ee)
Ph
CN
Ishitani, H.; Komiyama, S.; IIasegawa, Y.; Bohavas,hi. S . J. An1. Chent. SOC.,2000, 122, 762.
i-PrCHO
PhNIIOH , MqSiCN ,rt 5M LiClO, , ether 15 min
-
/INP
i-19
I OH
WA.: Lavijani, 11.; Emami, J.; Kararni, B. Tetruliedron k t t . , 2000, 41, 2471.
97%
2
ma r
Compendium of Organic Synthetic Methods, Vol 11
610
NC
CH2=CHCN*MeCN hv (254 nm) ,rt
* a +
t
Section 356
"+.
Bn-N 52%
Ishii.;Shimada, Y.; Sugiyama, S.; Noji, M.J.
26% Chetu. Snc., Pcrkin Truns. I, 2000, 3022.
*x
10% chiril Schiff base, bluene 10%Ti(0i-Pr), ,2 eq TMSCN
AN , C m
Ph
CN
82% (>99% ee)
1.5 i-PiOH (add over 210 h)
Ph NHCHPhz Krueger, C.A.; Kuntz, K.W.; Dzierha, C.D.; Wirschun, W.G.; Gleason, J.D.; Snapper, M.L.; J. Am. Chcni. Sac., 1999, 121, 4284.
N-CHPh2
NHCHPh,
N
H
2. HCN , 0 . 2 M in toluene -4O"C, 20 h
Ph
*
IIIII
H
Ph 96% (86% ee)
Corev.; Grogan, M.J. Oi-g, Left., 1999, I , 157.
-
SECTION 356: AMINE ALKENE
Ph 2eq Ph-Et , 100°C 5% Pd(OAch, LiCl, 36 h i-Pr2NEt, Bu,NCl
Roesch, K.R.;
Et
J. Org. Chem., 2001, 66, 412.
mNrnoc PhOTf , Pd(OAc)z, dppf MtCN , KzCO3, 9@l°C
*
N ,(H )F3oc Ph
70% Olofsson, K.; Sahlin, H.; Larhed, M.; J-lnllher~ A. .I. Org. Chetn., 2001, 66, 544.
75%
Section 356
61 1
Amine - Alkene
>95%
Blackhum, L.; Tavlor. R .J.YOrg. Lett., 2001, 3 , 1637.
1
-
Bu,
N/
t-Bu
30% CuI,NEt3 DMA , 110°C
4
Bu
t
86%
I
t-B u Kel'in, A.; Srornek, A.W.; Gevorevan. V. J. Am. Cheni. Soc., 2001, 123, 2074. Ph
0-rnentiyl
I
COC)&r<
Phd/N-ph
Ptl
20%GaQ3, DCE , I V ~ ~ U 3X ,h
Pfi
" I . ,
-
menthyl-0
60% (76:24 truns:cis) J. Ant. Clteni. Snc.. 2001, 123, 7182.
Kagoshima, 14.; Okamura, T.;
eC3H7F H7a0N BuLi ,TIIF, 0°C
82%
€B
c3
N(Bnp11
T,; Kawakami, M.; Fukui, M.; Yamashita, A,; Urano, J.; J. Am. Cheni. SOC., 2001, 123, 7734. d.
Bn,
BnNIIMe, P,l+ EtOH B(OW2 , It
,Me
Ph% 81%
Petdsls.; ... Boral, S. Tetrulze(lronLett., 2001, 42, 539. -SiMe,
PhCHO
ChzNH2, BF3QEt2 , MtCN
++L NNCbz
NI-ICbz
a
(84
Billet, M.; Klotz, P.; Miinn. A. TetruherlronLett., 2001, 42, 631.
I
16)
62%
612
Compendium of Organic Synthetic Methods, Vol 11
PEe
Section 356
-
(CH2=Q1),CuMgBr, I'IIF BF3*OEt2,-78°C
N
Me
QMT
I
Et Me ~ c . s . ; Simpson, I.D. Tr.truherlronLett., 2001, 42, 1179.
45%
NHEt
cat P m z ,K a , D i m ,
BnII%,
IOO"C, 6 h
I
Bu Bn Liu. f,.T.;Huang, 11.-L.; Wang, C.-L.J. Tetr-uhecfr-orrLa., 2001, 42, 1329.
V.
53%
S.X;Kobelikova, N.M.; Shchetnikov, G.T.; Kolomiets, A.F.; Bruneau, C.; Dixneuf.
ELL Synlctr, 2 U U Z ,
621.
/ococ6F5
10%Pd(PPh3)4, DMF
5 eq NEt3, MS 4A 110"C, 30 inin Kitamura, M.; Zaman, S.;
Ph-
CHO
's'
a
Ph
K. Synlett, 2001, 974. NIINHBz
NHzNIIBz , Sn(CIIzCH=CH2), 5% SC(OTf), , I-I,O/TIIF 30°C, 20 h
Kohavashi. S.;Hamada, T.; Manahe, K. Synlett, 200Z, 1140.
Ph 85%
Amine - Alkene
Section 356
rc"'
Me3si--<
613
L-
AcOII , PhMe ,50"C
MeOZC
Meo 79%
M.C.; Dale, J.W.; Bower, J. Synlett, 2001, 1149. In toluene, ethyl ester, catalyzed hy 15% ZnBr;? (90%). Ohnesorge, M.; Philips, N.G.; Bower, .I. Synlett, 2001, 1523.
*m
toluene ,pressurt: tube cat Pd(OAc), ,dppf
N I IPh
N
t-BuONa, Ar ,9o"C, 15 h
&
COzEt
81%
\
u; Yee, N.K. Tetruhedron Lett., 2001, 42, 2931. N €ITS
; Dale, J.W.; Hughes, D.D.;
0.2TsNHz , DMF , 1 h 2 KzC03 ,90"C
*
&
y
E
Fh
t 76%
I ( l m . ; Lee, 1I.F.; Lee, K.Y.; Kim, H.S. Tetruhedron Lett., 2001, 42, 3737.
PhNIIZ
-f
, PhNII,-IIC1,9 h
OH
cat [Ru3(CO),,J , 140°C. neat
Tokunaca. M.; Ota, M.; IIaga, M.-a.; Wakatsuki. Y. Tetruherlr-onLcltt., 2001, 42, 3865. OMe
Pt1-N.
pll
, DCE,rt
*
10% Srn12(thf), , 1 d
TMSO
61% Ph
Collin. J.; Jaher, N.; Lannon, M.I. Tetruherlr-on lxtt., 2001, 42, 7405.
Y,.
Singh, S.;
DNP-NIIOII , I j t C I ~ / F t C l ~ DNP = 2,4-dinitrophenyl
. Synrh. Coninnin., 2001, 31, 3087.
NHDNP
75%
614
Compendium of Organic Synthetic Methods, Vol 11
C6H13\
K
In, MeOH ,reflux, 4 h
XI
Ph
*
Section 356
J?
H/I///,/
87%
Ph
Yadav.; Bandyopadhyay, A.; Reddy, B.V.S. Tetruhedron Lett., 2001, 42, 6385, OMe
+
QMe 0.3 YhCI3, toluene 7ST,6 h
TMSO TMSO Ray, C.A.; Risherg, E.; m f ai. P. Tetruherlron Lett., 2001, 42, 9289.
..+ JN-NMe2 NMe,
3-
Me0
+ M ; k m e 2
TIIF,rt , 16 h
Ph
Me0
53% Breuil-Desvergnes, V.; Gore. J. Tetruhedron, 2001, 57, 19.5 1.
P
N
L
Me
P
h L
j
Rezaei, 11.; Marek, I.;
PhNIIN€I2
*
1 . 2 q M-Wr 2 . 3 cq ZnBr, 3. €130+
I
Tetruhedron, 2001, 57, 2477.
c
Me
ph
62% (88/12 dr)
acetophenone
\
Reheiro, G.L.;
me 22%
M%
Me-
55%
Ph
,N-BBu/Na3
,185"C, 1 h
*
ionic liquid medium Synthesis, 200Z, 370.
73%
Section 356
615
Amine - Alkene
4
E
PhffIO
t
O
2
n
Q
E
t
90%
4
urea, microwaves , 3 min
H Yadav, J.S.;Redy, B.V.S.; Reddy, P.T.Synth. Cointitun., 2001, 31, 425.
Bieliaca clay ,40"C, 5 h
Cl Sartori. G.; Bigi, F.; Maggi, R.; Mazzacani, A,; Oppici, G. Eiir. J. Org. Chem., 2001, 2513.
A
Ph
piperdine ,TIIF ,rcflux , 2 0 h
13
phmN
/
cat Rh(cod) BF4, 2 PPh3
55%
Tillack, A.; Trauthwein, H.; Hartung, C.G.; Eichberger, M.; Pitter, S.; Jansen; A.; &lh&. Monut. Chern., 2000, 141, 1321.
[CpZTi / P(0Eth
J3
1 2 , 0.03 M
THF
y ! + S P h
I
Bn
Takeda. T. Heterocycles, 2000, 52, 147. Fujiwam, T.; Kato, Y.;
Kardon, F.;
; Knausz, D. Tetruhedron Lett., 2000, 41, 8937.
1. 1.5 CpzTih4ez * 1.1M toluene, 110°C
phI[N3(f
2. flash chromatography Tehrani, K.A.; De Kimr,e.
N.Tetruherlron LcJtt.,2000, 41, 1975.
63~80%
0
61%
616
Section 356
Compendium of Organic Synthetic Methods, Vol 11
nph
4 JN-R
Ph ,TMSCI,It
25% Yb(OTf), ,DCM/TIIT: 0.25h
Ph
R=SOZTol R=Bn Org. Lett., 2000, 2, 159.
Yamanaka, M.; Nishida, A.;
D
B
F
1
2
,TIIF-H@
t
PdCl,(PPh3), , 40-80°C 2M NaZCO3 , 3 h
TfO
9
Ph
90%
0%
6rEt
Occhiato. E.G,; Trahocchi, A.; Guama, A. Org. Zm.,2000, 2, 1241. ph
N I ICOCF,
Pd2(dha)3, TIIF, ttinpp 80°C , 2 h , K,C03
t
ICHZCOzEt
/
ttmpp = tns(2,4,6-trimt:thoxyphenyl)phosphine Arcadi, A.; Cacchi, S.; Fahrizi, G.; Marinelli, F. Synlett. 2000, 394.
BCH,COzEt, hP f (
NHCOCF,
KzO3
DMSO, 80°C ,3.5h
+
H
73%
OTPm,.
Arcadi, A.; Cacchi, S.; Fahrizi, G.; Marinelli, Synlett, 2000, 647.
‘I
69%
f4GH7 52% Takeda, A.;Kamijo, S.; a o t o . Y.J. AIII.Clzeni. Snc., 2000, 122, 5662.
Section 356
Amine - Alkene
617
73% (95% ee)
; Villani, C. Tetruherlron Asyinrn., 2000, 11, 1681
Messina, F.; BQlliL M.:
(102i-h
1.3.5 q Na NII,/THF, --78"C 2. Me1
C02i-Pr
3. NH4Cl
i-PIo,C
dr
Donohoe. T .J.; McRiner, A.J.; Sheldrake, P. Org. Lett., 2000, 2, 3861.
a1
=
1. TMS , CUI PdClZ(PPh3)z
-
2. POCl, , i-PrzNH 3. 2 . 2 q Bu3SnH, AIBN 4.HjO" Ranler.;Kennedy, A.R. J. Org. Chern., 2000, 65, B213.
N''CHo
,MtCN
D
O
T
f
Pd(0Ach , dppf , KZCO3 -NMez tube, 80°C sealed
Olofsson, K.; 1-arhed, M.;
Bn-N
\
/
N
H
93~82~82%
Bn\N 40%
J. Org. Chrni., 2000, 65, 7235.
/H
\
99%
--
11
0
, 1S%TiC14
10% DMF,BOC CpRu(MeCN)yPFS *
rrost.; Pinkerton, A.B.; Kremzow, D. J. Ant. Clzeni. Soc., 2000, 122,
A0
12007.
618
Section 356
Compendium of Organic Synthetic Methods, Vol 11
fi
Ph
Martinez, I.;
ChTiMel, toluene ,70°C
*
0.25 M
Boc
Tetruhedron Lett., 2000, 41, 5607.
gBO
Ph
1. CHzClz 2. NEt3 ,reflux
B,HC
76%
b
Ph,C=GNPh 90%
. . . Shlmlzu.; Gama,Y.; Takagi, T.; Shihakami, M.; Shihuya, I. Synthesis, 2000, 517. MeH),
E:yozEt
10% 5% BuLi Pd(OAc),(PPh3) , THF , 2 0 T
3h Ph Me with CuI rather than Pd - 89% in 2 h Tetrahedron Lcttt., 1999,40, 1301.
I
Clique, B.; Monteiro, N.;
79%
acetophenone ,KOt-Bu
':I
DMSO , 2 h
NH,
Moskalev, N.; Makosza, M. Tetrulierlron Lett., 1999, 40, 5395.
H
5M 0.95eq LiClO,.ether &TFA N%*
N
co. P A ; Kaufman, M.D. J. Org. Cheni., I Y Y Y , 64, 6041.
1) 53%
Section 356
Amine - Alkene
5H
=
PhHN
619
i-Pr2NH , (WHO),, , CuI
*
dioxane , reflux , 11 h
c N - P h 75%
Jayaprakash, K.; Venkatachalam, C.S.;Balasublamanian,K.K. Tetruhedron Lett., 1999, 40, 6493.
Ir
Me cat Pd(PF%3)4 , 4 PhI
4 K2C03,dioxiuie rEflux
ph$
*
Ph
N-Mts
N-Mts
+
NHMts
18) 80%
Ohno, €I.; Toda, A.; Miwa, Y.; Taga, T.; Osawa, E.; Tainaoka, Y.; Fujii, N.; J. Org. Chem., 1999, 64, 2992.
p
h
=
Bn2NH, dioxane , 100°C 5% Pd(Pl’h3)4, 10% l’hC02II
*
Ph
NBn,
aTs
98% Kadota, I.; Shibuya, A.; Lutete, L.M.; Yamamoto. Y,J. 01-8.Cliern., 1999, 64, 4570. 1. BuCrCI’s, DCM , rt , 5 h 2. 2 NJ L D A , TIIF, -78°C
NI-IBn
*
3. hasic alumina
Back.;Nakajima, K. Org. Lett.. 1999, 1, 261.
94%
I
Bu
Bn
87% (84:16 E:Z) IIhai‘eh, S.; Latiri, Z.:
Synrh. Cnr~urzun.,1999, 29, 981.
REVIEWS: “Addition of Cabon-Centered Radicals to Irnines and Related Compounds,” Tetrulierlron, 2001, 57, 5461.
620
Section 357
Compendium of Organic Synthetic Methods, Vol 11
"RecentDevelopments in Imino-Diels-Alder Reactions," Buonora, P.; Olsen, J.-C.; Tetruhedron, 2001, 57, 6099. "Generationand Reactivity of a-Metalated Vinyl Ethers,"Friesen. R.W, J. Chem. SOC., Perkin Truns. I , 2001, 1969.
SECTION 357: ESTER - ESTER
81%
Ixe, C.W.; Gruhhs. R.H,J. Org. Chem., 2001, 66, 7155.
w
c
r
r
o
2eqAczO
-
0.2%FeC13 0°C ,30min Eost. B M ; Lee, C.B. J. Ant. Chem. SOC.,2001, 123, 3671.
67% OAc
73% (99% ee ,99: 1 syn:anti) Evans. D.A.; Scheidt, K.A.; Johnson, J.N.; Willis, M.C. J. Am. Chem. SOC., 2001, 123, 4480. Ac@ , zeolite H Y , 10 h
Kamesh, P.; Reddy, V.L.N.; Venugopal, D.; Suhrnhmanyam, M.; u t e s w a r l u . Y, Synth. Comniun.,2001, 31, 2599.
Section 358
621
Ester - Ether
LOTS
4
Ph
Ph -30°C Hirt, IJ.11.; Schuster, M.F.H.; French, A.N.; Wiest, O.G.; Wirth. Eur. J . Org. Chcm., 2001, 1569.
3% VOC13, 2 eq Z n , 2 eq Ac20
PhCIIO
~
80°C
65% ee
T.
'uPh
Ph
OAc
85% (80:20 dkmeso)
Uirao. T.; Takeuchi, 14.; Ogawa, A,; Sakurai, H. Synlett, 2000, 1658.
'0 Cho, C.S.; Back, D.Y.; Kim, 11.-Y.; Shim. S.C.: Oh, D.H. Synth. Conzmun., 2000, 3% 1139.
R EV I E WS : "1, 2-Diacetals: A New Opportunity for Organic Synthesis," L y . S.V.; Baeschlin, D.K.; Dixon, D.J.; Foster, A.C.; Ince, S.J.: Pnepke, 1I.W.M.; Reynolds, D.J. Chem. Rev., 200Z, 101, 53. Section 312 (Carhoxylic Acids - Carboxylic Acids) Also via Dicarhoxylic Acids: I1 ydrox y-esters Section 327 (Alcohol - Estcr) Section 323 (Alcohol - Alcohol) Diols
SECTION 358: ESTER - ETHER, EPOXIDE, THIOETHER PhSC02Me Bu-
t
'"h
Pd(FQ3h , 110°C phs toluene, octane I-Iua, R.; Takeda, €4.; Onozawa, S.-y.; Abe, Y.; Tannka. M. J. Ant. Cliem. Soc., 2001. 123, 2899.
96%
COzMe
622
Compendium of Organic Synthetic Methods, Vol 11
@c"' /
ax C02Me
1% Ru catalyst, hexane
-
-5"C, 72 h
Oi-Pr
/
98% (98% ee)
; Grdzini, M.V.A.; Aouad,
O H -o1F
Section 358
E. Org. Lett., 2001, 3, 1475.
-
Dess Martin periodinane
CH2C12,rt , 3 5 inin
QOh
92%
Roels, J.; Metz. P, Synlett, 2001, 789.
HO,C
PhSeSePh , DDQ MeCN , 3 0 T
*
&SePh
0
Tiecco. M.; Testaferri, L.; Ternnperini, A.; Bagnoli, L.; Marini, F.; Santi, C. Synlett, 2001, 1767.
c;"
DCMIhexane , 4 h
[PhS€I/BuLi], -50°C
E O 2C
95%
;""%F * 2 v s f i
cogt
CO2Et
PhS
(40
60) 91%
K i m h u A ; Kawahara, F.; Omata, Y.; Murakanii, N.; Morita, R.;Otake, H.; Mitsudera, H.; Shirai, M.; Kakehi, A. Tetruhedron Lett., 2001, 42, 8497.
5% Grubbs' catalyst II 0.05 M , DCM , 4 0 T
-
CH2€ IIPh
0
4
4 81%
Choi, T.-L.;
n
Chent. Contmun., 2001, 2648.
HNYo
PhSH , GH70II ,C,H,ONa 6h
*
PhS
. . 0 L* h h.J.u J L ; Uegaki, M.; Sakai, M.; Takeda, Y. Tetruhedron, 2001, 57, 21 15.
NH2 98%
623
Ester - Ether
Section 358
bP
0
-
(---J?
<M,-40°C-+
rt, 12h
Ph
*
Me
I
Me
63% (33% ee) Rudler.; Parlier, A.; Certal, V.; Frison, J.-C. Tetruhedron Lett., 2001, 42, 5235.
phj
N,=CHCOzEt, DCM
*
h,,\\+' C C O Z E t
1% Rh@)catalyst , 40°C
-D
SPh
Ph
+
(66
phLc €
B
SPh
:
34) 81%
Kitagaki, S.; Yanamoto, Y.; Okuho, €I.; Nakajima, M.; Heterocycles, 2001, 54, 623. ,8%[Pd(OAc)zK] 13% NPMoV
0 2
MeSO-14. M d H 50"c, d h NPMoV = molybdovanadophosphate Lett., 2000, 2, 523. Kishi, A.; Sakaguchi, S.; - 0 r g .
)yl
OMt:
hv,MeO€I rt.10h
Ji, S.-J.; JIoriuchi. C.A. Bull. Chem. Soc. Jpn., 2000, 73, 1645.
CozPh
PhMgC1, TIlF, -45°C
-
OMe
rt
0 Jung, M.E.; Mengel, W.; Newton, T.W. Synth. Conzmun., 1999, 29, 3659.
95%
Section 359
Compendium of Organic Synthetic Methods, Vol 11
624
1. Cp2TiC12/i-BuMgBr,T€IF PhSSh
-10°C
-.,
0°C
PhSCHZC02Et
/
2. BICII2CO,Et, THF-HMPA
HuanL1.; Zheng, W.-X.
80%
Synth. Contmun., 1999, 29, 1297.
I
I
56% (>98:2cir:trrms)
OMe OMe Crousse. B.; B6gu6, J.-P.; Bonnet-Delpon, D. J. Org. Chem., 2000, 65, 5009.
(LC1
Ce(SO.+)4*41 1 2 0
0 2 ,
He, L.;
--
&OH, 5 0 T , 8 h
0
MtO
m.C..ABull. Chern. Soc., Jpn., 1999, 72, 2515.
SECTION 359: ESTER - HALIDE, SULFONATE
Rozen. S.; Ben-David, I. J. Org. Chem., 2001, 66,496.
Ph
y
o
--
10% ammonium salts, TIIF -78°C + It, 3 h
c1
* p h - c O 81%
Q
Wack, €1.; Taggi, A.E.; IIafez, A.M.; Drury J. Am. Cheni. SOC., 2001, 123, 1531.
c
l
1TI, W.J.; Lctka. T.
(99% ee)
C6Q5
65%
625
Ester - Ketone
Section 360
FeCb ,NaI , MeCN
*
reflux
go 76%
Oavan. s9,; Sharma, A.K. Tetrahedron Lett., 2001, 42, 4923.
dilmroyl peroxkle
PhH , reflux 89% (5.4:l dr)
Ollivier, C.; Bark, T.; Renaud. P. Synthesis, 2000, 1598.
I, , aq MeCN , 16 h
t
reflux 98% (919 fruns:cis)
& d 6
0 Ua. H.-J,; Lee, S.-Y.; Park, Y.-S. Synth. Comiiiun., 2000, 30, 3645.
SECTION 360: ESTER - KETONE OBZ D 10%Ybc1~ CM,rt
10%TsOIJ MeN02 ,It
t
4
84% (96%Jee)
Zhu, Y.; Shu, L.; Tu, Y.;
77% (97% ee)
. I . Org. Chent., 2001,
Curulu~uunturcticu lipase B 10 torr ,40"C
Ph CBrdova, A,;
oBz
66,1818.
* Ph-0
K.D. J . Org. Chern.,2001, 66,1906.
AA 95%
Compendium of Organic Synthetic Methods, Vol 11
626
4
C
N
>.!
C6H13
pph3
D; Yu, C.-W.;
2
Ph
Section 360
,MeOH, acebne It
-u 0
82%
Yuen, W.-H.; Yang, D. J. Org. Chem., 2001, 66, 3606. -78°C ,CHzClz
_(OTBS
i
-
k
ui-pr (t-Bu)S
88%, 79% II 0 Harada.;Iwai, H.; Yakatsuki, €1.; Fujita, K.; Kuho, M.; Oku, A. Org. Lett., 2001, 3, 2101. S(t-Bu)
9
BIC13zC0zMe, PhH AIBN ,80"C, 4 h Miura, K.;Fukisawa, N.; Saito, H.; Wang, D.;
ph 86% Org. Lett., 2001, 3, 2591.
*
1. EtzZnCHzI 2. cat TMSCl
Me 0
Hilgenkamp, R.;Tercher. C.Y, Org. Lett., 2001, 3, 3037. &COZEt Ph
Ac@ , MgJDMF +
TMSCl
63%
Ph
64% COZEt
flazcy:\
Ohno, T.; Sakai, M.; Ishino, Y.; Shihata, T.; Maekawa, H.; &d&&LL Org. Lett., 2001, 3, 3439.
-
1.2.5 eq TMSCl, THF 2.4.5 -78°C eq S d z ,-10°C THF *@rZc6H13
Me-
N Ph
3 . 4 eq IIMPA 4.1120
McDonald.;Galka, A.M.; Green, A.I.; Keane, J.M.; Kowalchick, J.E.; Micklitsch, C.M.; Wisnoski, D.D. Tetruliedron Lett., 2001, 42, 163.
Ester - Ketone
Section 360
627
2 eq IZn(CHz),C02Et1 20°C 7'IIFJtolueneJDMF , 2 2 h
* L
1.5% P d S
C7H15
C
C7H15
0
PhI(0Ach ,TsOH
O
T
s
~
&:
t
Ph+rs
microwaves, <1 min
Lee., Choi, J.-H. Synlett,
E
91%
Shimizu, T.; Seki. h.1, Tetrahedron Lett., 2001, 42, 429.
PhL
2
88%
OTs
2001, 234.
SmIz, THF , IIMPA
80%
-78"C, 10 min
Chung, S.11.; Cho, M.S.; Choi, J.Y.; Kwon, D.W.;
Mn(OAc), , PhH ,reflux
* &OAc
10 h '
64%
. ; Sezen, B.; Iyigiin, C.; Ehnnali, 0. Tetruhedron Lett., 2001, 42, 6397. 0
, NaOt-Bu
-Br
CO2Et A1203,
COzEt
t-BuOH , 180°C
in vmuo , 2 h
&
Bhar. S.; Chaudhuri, S.K.; Sahu, S.G.; Panja, C. Tetruhedron, 2001, 57, 9011.
NaH ,MeOCOzMe
*
Jung, J.-C.; Jung, Y.4.; park. 0.-S. Synth. Comzniun., 2001, 31, 1195.
0
84%
628
Compendium of Organic Synthetic Methods, Vol 11
Section 360
0
II
X I 4 , i-Pr,NEt , DCM
i-Pr-C02Ph
-2O"C, 3 h Tanahe.
Y,;Hamasaki, R.; Funakoshi, S. Chem. Commun., 200Z, 1674.
JX I
Ph
72%
b N
1. CII2=CHC02Me, TIW,6 h 10% RhCI(PPh3)3,135"C 2. aq HCI
* I'h LCOzMe
&:
Willis. M . 6; Sapmaz, S. Chem. Commun., 200Z, 2558.
Mn(OAc), PhH, 8h
*
73%
61%
El0 El0 m v e l i . C,; Sezen, B. Tetruhedron Lett., 2000, 41, 7973.
d
*
65%
LHMDS
Krdus.; . . Dneprovskaia, E. Tetruhedron Lett., 2000, 41, 21.
w; Kiihler, V. Org. Lett., 2000, 2, 1597. .
1
0 3
Ph Mahmood, S.J.;McLaughlin, M.;
, Me011 , DMS
-78°C
w
C02Et
77%
ynth. Cotnmun., Z999, 29, 2967.
Section 361
Ester - Nitrile
629
C02Me
Ph
=
CO, Rhb(C0)16, MeOH
Ph
130°C. dioxane
Yoneda, E.; Kaneko, T.; Zhang, S.-W.; Onitsuka, K.; Tetruherlron Lett., 1999, 40, 781 1 .
'9
0
DCE , 0.1 M ,rt , 2 h 5% [Rh(dppb)Cl],/AgSbF6
Lev. S.V,; Thomas, A.W.; Finch, €1. J. Chcm. Soc., Perkin Truns. I , 1999, 669. 1 . Zn(OAc)2, aq AcOII XOOC, AcOH
OMS
2. Ac@ , Py
Nagasawa, K.; IIori, N.; Koshino, H.; Nakata. T. Heterocycles, 1999, 50, 919.
70%
Section 320 (Carboxylic Acid - Ketone) Section 330 (Alcohol - Ketone)
Also via Ketoacids Hydroxyketones
-
SECTION 361: ESTER NITRILE
TMSCN ,THF ,4h 5% LiOMe ,22"C
CN oms (96 4) >99% Wilkinson, H.S.; Grover, P.T.; Vanddenbossche, C.P.; Bakale, R.P.; Bhongle, N.N.; Wald, S.A.; Senanavake. C.H. Org. Lztt., 2001, 3, 553. 0
Section 362
Compendium of Organic Synthetic Methods, Vol 11
630
Dcc
*
t-BuOH Org. Lett., 2001, 3 , 3733.
75%
COzf-Bu
EtOzC--CN ,-24"C, 4 h modified Cinchona alkaloid Tian, S.-K.;
1
ph
Snndherg, M.;
OAc
-1
J. Am. Chetn. SOC.,2001, 123, 6195. Me-,SiCN -78°C
,TiCi, , DCM 4
rt , 2 h
Org. LEtt., 2000, 2, 687.
5 eq MeOzC-CN, THF
A
Berthiaume, D.;
76% (95% ee)
20 eq DIPA, r t
. Tetruhrdron, 2000, 56, 5995.
7c
92%
CN
*zxl
cat Cp2-Sn(thQz, toluene ,rt , 3 h c-)Ho
Ph
94%
-
'
86%
Kawasaki, Y.; Fujii, A.; Nakano,Y.; Sakakaguchi, S.; Ishii.Y..I Org. . Chem., 1999, 64, 4214. 10 eq M e 0 2 C - C N , THF
20eqDIPA,rt, 18h ; Berthiaume, D.; Boivin, R.P. Synlctt, 1999, 1423.
SECTION 362:
ESTER - ALKENE
This section contains syntheses of enol esters and esters of unsaturated acids as well as ester molecules hearing a remote alkenyl unit.
Ester - Akene
Section 362
b+ 63 1
PhSH , CO , P~(OAC)~/RR-DIOP phs 400 psi ,DCM ,110"C
1n.4~
Xiao, W.-J.;
5% Pd(OAc)z, 6 eq bpy AcOI1,6O"C, 10 h
0
0 Zhang, Q.; JA.-&;
71% (89% ee)
0
J. Org. Chem., 2001, 66, 6229.
-
A& -
Nan, X. J. Org. Cheiit., 2001, 66, 7676.
?H
QH MqSiC-CH ,2S% SnC14, 3 h
&
SO% BuLi, PhCl, 105°C
T"J\i..
Kohayashi, K.;
'
90%
Org. Lett., 2001, 3, 241.
%iY%%?&S5"C, * 12 h
/ Ilu, Y.;
Org. LcJtt., 2001, 3 , 1387. NaOMe , MeC€I(C02Me)2
5% Pdz(dhah-CIIa3,TIIF* Ci DPEphos ,70"C, 3 h Ogasawara, M.; Ikeda, H.; Nagano, T.; CqMe
/(=c ..
53%
=c94%
- 2 T C 0 2 @
C02Me Org. Lett., 2001, 3, 2615.
1. DABCO, H@/THF rt , 15min
C02Me
(ph2. NaBI-14,rt , 15 min Br BdSnVdirlh.; . Kumaraguruharan, N. TetrulzedronLett., 2001, 42,477. Ph
i-Pr
j
83%
632
Compendium of Organic Synthetic Methods, Vol 11
i
(75 86% ee: . H.M.L; Ren, P.; Jin, Q. Org. Lett., 2001, 3, 3587. OMe
mso]
PhCHO
=-
10% CuF*S-tol-BINAP
-
Pp Br
NHAc I I\L COzEt
cqa
67%
3, xm +
-
Ph
Bluet, G.; Bazhn-Tejeda, B.;
25) 66% ee
Section 362
Ph
(86 14) 85% Org. k t t . , 2001, 3, 3807.
,E M
t-BuOK 10% Pd(dha)z IR-BINAP
Ogasawara, M.; Ikeda, H.; Nagnno, T.;
- c=AN Ph
C02Et C0,Et
98% (75% eeR) J. Am. Chenz. Soc., 2001, 123, 2089.
Ru enoic carhene complex CII,CI,, refhx, 3 h
Buo+
€3 u 0
0 87% Choi, T.-L.; Lee, C.W.; Chatterjee, A.K.; Gruhhs. R . f t J. Am. Chem. Soc., 2001, 123, 10417.
Ph
=
SMe
1 . TsOII ,CI12C12,r t , 17 h 2. so,
0Ts -A.I,.; . . Emmerich, D.J.; Silveira, C.C.; Matins, T.L.C.; Rodrigues, O.E.D. Synlett, 2001, 371.
82%
Section 362
633
Ester - Alkene
SiMe, CO/H2, PhH ,90"C , 3 h
*
0.25%Rhd(C0)12 "OH Fukuta, Y.; M,&&J,
PhSII , a t Pd(OAc)2/dppp P-TsOH, THF, llO"C, 6 h
-
C3H7
92%
; Itoh, K. Tetrahedron L.ett., 2001, 42, 1301.
co
300 psi
* C3II7
%sB
0 El Ali. B.; Tijani, J.; El-Ghanam, A,; Fettouhi, M. Tetrakedron Lett., 2001, 42, 1567.
86%
cat R u ~ ( C O )5~atm ~ , CO V
o
1
l
0
NEt, ,rt
71% Yoneda, E.; Zhang, S.-W.; Onitsuka, K.; Takahashi. S. Tetrahedron Lztt., 2001, 42, 5459.
.
.
90% (955 E:Z) Syntk. Coiitniu., 2001, 31, 2055.
TMSOTf , PhH
C0,Me
reflux, 30 min
Ph 86% (97:3 Z E )
Ravichandrnn, S. Synth. Coiitrnrrn., 2001, 31, 2345.
P h =
C O , MeOH , &Br2 PdBr,
Me02C Li, J.; Jiang.;Chen, M. Synrk. Coinmu., 2001, 31, 3131.
76% (77:23 Z E ) C02Me
634
Section 362
Compendium of Organic Synthetic Methods, Vol 11
4% CuCl , MeOH
co2rI
reflux, 2 h
h k L ; Yu,Z.; Wu, S. Tetruhedron, 2001, 57, 1585 TiC13 ,LiAlH, ,THF
C02Me
C02Me
reflux, 1 h
Ph*
46% (88: 12 E:Z)
Shadakshari, U.;Navak. S.l(. Tetrdiedron, 200Z, 57, 4599. hv , DCM , -40°C HOCHzCI IzNMe2 COzR*
R*=
0 ,&)
81% (83% de)
Ph Bargiggia, F.; Piva. 0,Tetrahedron Asynim., 200Z, 12, 1389. B K H 2 C 0 2 E t , toluene, K2C03
*
PhCHO
2% PEG-supported TeBu , cat P(0Phh
IIuang, Z.-Z.; Ye, S.; Xia, W.;
mCqEt
Ph
Cheni. Commun., 2001, 1384.
1. -%Me3 ,Gaa3 methylcyclohexane 2. THF, 10M HCI
EtS
%
98% (>99:1E:Z)
EtS
Ph
T M s o k p h Arisawa, M.; Miyngawa, C.; Yoshimura, S.; Kido, Y.; Cheni. Lett., 2001, 1080.
5% MeC02H ICpRuCl(cod)] ,imprene, ,40"C 20h m > e :
2
O H,+=
*
HO La Paih, J.; DCrien, S.; Bruneau, C.; Demerseman, B.; Toupet, L.; pirmeuf. P.H . Angew. Chern. Int. Ed., 2001, 40, 2912.
85%
Ester - Alkene
Section 362
AB*
635
e- ,Bu,N C D 4* p h + P h
Ph
phw;;
+
PhC4
0
Pb cathde/MeCN 65% 0% Sn cathde/MeCN Klse.;Ueda, N. Bull. Chern. SOC. Jpn., 200I, 74, 755.
24% 78%
pH
MeS
)=c=o
C1
57%
xylene ,reflux , 8 h
Lleh.;Benet-Buchholz, J.; FLcke, T.; Fischer, R.; Graff, A.; Lefehvre, LM.; Stetter, J. Tetruherlron, 2001, 57, 4133.
-
LiBr, AcOH ,80"C C02Et
Ma. S.; Li, L.; Wei, Q.; Xie, €1.; Wang, G.; Shi, Z.; Zhang, J. Pure. Appl. Chcm., 2000, 72, 1739.
Q
cat Cu-Na-€la-320
zeolite
lph
O O ' B
-
%Me
,80"C, 21h
60%
t-B"/Ob Carloni, S.; Frullanti, B.; Maggi, R.; Mazzacani, A,; Bigi, F.; Sttrtori. G , Tetruhedron Lr.tt., 2000, 41, 8947.
(m)5% M a
TEIF,heat roEl ,3.25 h
'Ac
Good, G.M.; Kemp, M.I.; Ken. W.J, Tetrahedron Lett., 2000, 41, 9323.
69%
636
Section 362
Compendium of Organic Synthetic Methods, Vol 11
1. CpzZrEtz 2. ClC0,Et
P h = P h
*
3. HCI
phvph 70%
\
COzEt
Takahashi.; Xi, C.; Ura, Y.; Nakajima, K. J. Ant. Chem. Soc., 2000, 122, 3228.
5e q o , l o % Pd(OAc), 5 eq NaIIC03 ,Bu4NCl DMF ,60°C
'"I*,,
Gagnier, S.V.;Larock. R.CI.J. Org. Chem., 2000, 65, 1525. 1% R u ~ ( C O )100°C ~~, 10 atm CO , dioxane 0
Yoneda, E.; Kaneko, T.; Zhang, S.-W.; Onitsuka, K.; polymer- supported triflating reagent i-Pr,NEt
-
99%
ooT 95%
Wentworth, A.D.; Wentworth .Ir. P,; Mansoor, L J . F . ; nOrg. Lett., 2000, 2, 477. PhSH , Pd(OAc)Z, PPh3
Rs
400 psi CO ,DCM * llO"C, 60h 0 Xiao, W.-J.; Vasapollo, G . ; Alper. H. J. Org. Chem., 2000, 65, 4138.
83%
Et c 3H7
EtI , Pd( PPh,), , KZCO3 MeCN ,70"C, 5.5 h COZH
ROISI.;Bellina, F.; Biagetti, M.; Catanese, A.; Mannina, L. Tetruherlron Lett., 2000, 41, 5281.
0
Ester - Alkene
Section 362
a
637
Ph
I
,DMF , Py
Pt1-m
5% Pd(OAcb, BudNCl, 2 d *
OH
Kadnikov, D.V.;
I
Org Lett., 2000, 2, 3643.
qMe, )tn/. EtzMtSiII , DCM slow addition ,25"C, 1 h * Me02C
Ph
OCOzMe
93% Muraoka, T.; Matsuda.; Itoh, K. J . Am. Chem. Soc., 2000, 122, 9552.
hC1 C02Et
1. 2 eq SmI, ,THF , rt 2.1MHCl
C7k11.5
* C7H15
Me
T
CO&t
75%
Me
Concell6n, J.M.; Pbrez-AndrBs, J.A.; Rodriguez-Solla, €1. Angew. Chem. Int. Ed., 2000, 39, 2773.
Ph
=
1. Cpgzr(rI)a 2. co
3. Ph.%SePh
*
fi\
R-
0
ep
76%
Synrh. Commun., 2000, 30, 887.
Zhong, P.; Xiong, Z.-X.;
NaBH4,10% Pd(OAc)z, 20% PPhS, THF , =flux
m;Savic, V. Chem. Commun., 2000, 2381. PI1
=
1. CpzZr(H)CI 2. co 3. PhSC1
Zhong, P.; Xiong, Z.-X.; lluang.
t
Ph-Ysph
Synth. Commun., 2000, 30, 2793
II 0
80%
Section 362
Compendium of Organic Synthetic Methods, Vol 1 1
638
w
4 eq Mn(0Ach ,AcOH Ac20 ,reflux ,20min
=
78%
0
Montevecchi.; Navacchia, M.L. Tetrahedron, 2000, 56, 9339. 1. LiAIH,, NaOMe 2. I,
,-/
3 . cat PdC12(PPh3)2,5 atm CO KzCO3, TIIF, 1 d
HO Liao, B.;
d
-’
Heterocycles, 2000, 52, 1241.
(CIIZhPh
0
1. 1% Pd(PPh3)4, CO , MeOH rt, 18h
2.2.2eq MezCuLi, ether -78°C- 4°C
40
76%
(CH2la
J . G . Ainge, ; S.W.; Baxter, C.A.; Eastman, T.P.; Harwood, S.J. J. Chcnt. Soc., Perkin Truns. I , 2000, 3188. ~
cc
52~54%
-”%”
PdQ(PPh3)2, K2C03 ZnCI2, NMP ,19h
Ph
80-90°C
Iver.;Ramesh, C. Tetruhedron Lett., 1999, 40, 4719.
Mingo, P.; Zhang, S.;
Ph
J. Org. Chem., Z999, 64, 2145.
61% (3:lE:Z)
Section 362
639
Ester - Alkene
PhSII , CO ,THF , 6 h cat Pd(OAc), ,dppp
SPh
*
76%
110°C
J. Org. Chem., 1999, 64,2080.
Xiao, W.-J.; Vasapollo, G.;
Ph Li, J.;
CO ,MeOII , PdC1, , 3 CuC12
=
*
Jianl..;Feng, A.; Jia, L. J. Org. Chem., 1999, 64,5984.
"YZ Ph
aCozMe ,DMF , lOO"C,
Me-t-Bu
/
2% Pd(OAc)2, 4% P(o-TOl)s 0.3% NEt3 , NaOAc , 1 d
I
+
Larock. R.C,; Doty, M.J.; Han, X. J. Org. Chem., 1999, 64,8770. c71115
4 ~XJ CUClZ , McCN
CO2II
*
25"C, 50 h
t-Bu
I 72% &
b0 52%
c7H 15
Ma. S,; Wu, S . J. Org. Chem., 1999, 64,9314.
M%NCIiO, 50°C, 6 h C 8 H 1 7 w I + p BFih
YChldl.; . .,. Yamamoto, S.; Sato, K. Chenz. Conzmun., 1999, 1363. = 2 - B
PhCOOZI, dioxane ,rt 5% RuCl(cod)(CSMq), 15 h
83%
Ph-fyOBZ
98%
Ph
Le Paih, J.; Dkrien, S.; m e u f . P.H. Chenz. Comnzun., 1999, 1437. P hCI I 0
EtOzCCIIzCN , 5 min microwaves
*
P h T c ( ? ? E t
CN
Mitra.;De, A.; Karchaudhuri, N. Synth. Cornrnun., 1999, 29, 2731.
97%
Compendium of Organic Synthetic Methods, Vol 11
640
Lu
OTBS
Section 363
&
OAc
OTBS
1.03
2. *OM" OLi
Keck.;Li, X.-Y.; Knutson, C.E. Org. Lett.,
0
89%
1999, 1, 411.
Arcadi, A.; Cacchi. S.; Fahrizi, G.; Marinelli, F.; Pace, P. Eur. J. Org. Chem., Z999, 3305.
P h = Li, J.;
CO/MeOH ,PdClz ,CClZ
64%
NaOAc, PhH Jia, L. Synth. Continun., 1999, 29, 3733. Ph
I
/ \
DMAC ,100"C , K z O 3 , 8h 0
Uernura, K.; Shiraishi, D.; Noziri, M.; b o u e . Y. Bull. Chem. SOC. Jpn., 1999, 72, 1063. Related Methods:
Section 6OA (Protection of Aldehydes). Section 180A (Protection of Ketones). Also via Acetylenic Esters: Section 306 (Alkyne - Ester). Alkenyl Acids: Section 322 (Carbxylic Acid - Alkene). p-H ydroxy-esters: Section 327 (Alcohol - Ester).
SECTION 363:
-
ETHER, EPOXIDE, THIOETHER ETHER, EPOXIDE, THIOETHER
See Section 60A (Protection of Aldehydes) and Section 180A (Protection of Ketones) for reactions involving formation of Acetals and Ketals.
Section 363
Ether - Ether
641
PVC anode, Pt wirecathod e- ,0.1 M EtdNOTs ,THF 30% MeOH ,2,6-lutkline
Sun, Y.; Liu,
OMe 94% B.; Kao, J.; Andre d'Avignon, D.; J4oeller. K.D. Org. Len.,2001. 3, 1729.
05
CH(0Me )2
TI(N03), , MeOH, 0°C
5 min
*
87%
%
rerrdz.;Silva Jr., L.; Vieira, T.O. Tetruhedron, 200Z, 57, 1709. 4
,
SEt
Vi-In], 2 eq Zn , DCM ,rt , 1 h ~
SEt
P$h,
Ph SEt 95% (49:51 dkmeso) Chem. Lett., 2001, 640.
Yoshimura, N.; Igurashi, K.; Funasaka, S.;
Et,NSiMe, , 2 eq Me1 toluene, 90°C Ohshita, .I. Iwata, ; A.; Tang, H.; Yamamoto, Y.; Matsui, C.; Cheni. Lett., 2001, 740.
1. Bu3SnH, toluene BEt, ,-78°C 2. air, -78"C, 3 h 3.1M NaOII , it , 12 h
-
76%
OSiMe3
65% (>98% ds)
Villar, P.; Equey, 0.;Penaud. P. Org. lxtt., 2000, 2, 1061.
OMe Yadav. J.S,; Reddy, B.V.S.; Hashim, S.R. J. Chern. SOC.,Perkin Truns. 1, 2000, 3082.
Section 364
Compendium of Organic Synthetic Methods, Vol 11
642
PhCHO
Mn/TMSCIICpzTiC1,,THF
*
Phq
P
0°C. 1 d Dunlap, M.S.;
SECTION 364:
O -H Yang, X.-F.; Mague, J.T.;
Synth. Conunun., 1999, 29, 1097.
b
oms
73% (13:l dr)
-
ETHER, EPOXIDE, THIOETHER HALIDE, SULFONATE
PhCHO ,InC13, DCM + It ,overnight
(>, @@\
u.C . J . J. Org. Chem., 2001, 66, 739.
Ph
85%
Gomtsvan. A,; Koenig, R.J.; Lee, C.-H. J. Org. Chem., 2001, 66, 3613.
BF,.OEt,, AcOH 61%
hexane ,-78°C Jaher, J.J.; Mitsui, K.; w v s k v . S.D. J. Org. Chem., 2001, 66, 4679.
1-0
Me0 Me0 b v . S.C.; Guin, C.; Rana, K.K.; Maiti, G . Synlett, 2001, 226.
87%
Ether - Halide
Section 364
Li, J.;
643
95% (3: 1 cis:trans)
u.C . 4 , Tetruhedron Lett., 2001, 42, 793.
Albert, S.; Robin, S.; Bousseau. G , Tetruhedron Lett., 2001, 42, 2417.
Br
Talyhov, G.M.; Mekhtieva, V.Z.; Karaev, S.F. Run. J. Org. Chem., 2001, 37, 600. 0 $% .%
QSiC13 -
SiCl, , i-Pr,NEt CHZClz, -85°C
---
fiB
&h
* Ph
5% fluorinatedarene ligand
Ph
88% (94% ee)
--
C1
Tao, B.; Lo, M.M.-C.; Fu. G.C. J. Ant. Cheni. Soc., 2001, 123, 353. OSiMe3 Bn-NnN+CF3 - H ph
Ph
+
10%CsF, 0°C , glyme, 5h
86% CF3
; Blond, G . Tetruhedron Lett., 2000, 41, 8777.
-013
NaIO, / NdI SO3
Okimoto, Y.; Kikuchi, D.; Sakaguchi, S.;
MeCN
-06
% I
61%
Tetruhedron h t t . , 2000, 41, 10223.
Section 365
Compendium of Organic Synthetic Methods, Vol 11
644
MeOH , dioxane, rt ,0.75 I2
0.25 C e ( 0 T G
O
l %' ##
M
Y
~ Z X J LShekarriz, ; M. Tetruhedron Lett., 2000, 56, 5209.
L
P hCI I 0 ,IIIC13
-
APh 81%
PI1 Ph Yang, J.; Viswanathan, G.S.; Li. C-L Tetruhedron Lett., 1999, 40, 1627. Et,NSiMe, , 2 eq Me1 80-90°C , 5 h ; Yamamoto, Y.; Matui, C.
Ohshita, J.; Iwata, A,; Kanetani, F.; J. Org. Chern., 1999, 64, 8024.
81%
SECTION 365: ETHER, EPOXIDE, THIOETHER - KETONE
6'
"
tlco
e
+
R
, cat TMSOTf
0
MtCN , -30°C
-
rt , 10 min
* &SMe
94%
Matsugi, M.; Murata, K.; Gotianda, K.; Nambu, H.; Anilkumar, G.; Matsumoto, K.; U t a . J. Org. Chem., 2001, 66, 2434.
pms f
1. c3rr+xo,
Y.
M ~ S Ort~ ,
2. (EtOzCkO, EtOII , rt 3. BF3.OEt2, DTBMP EtO,C/ DCM ,0°C
C ,€I, Cohen, F.; MacMillan, D.W.C.;
7 2 ~ 8 7 %(87% ee)
; Romero, D. Org. Lett., ZOOZ, 3, 1225.
Section 365
Ether - Ketone
645
-4
PhSH , TIIF, LiAl-ply2a 30 min
-G;. 7
SPh
Prahagaran, N. Org. Left., 2001, 3, 389.
.
95% (41% ee)
APh
chiral phase transfer agent, PhMe
Ph
*PhA
aqNaOCl,lt
P 98% (86% ee)
Lvea.;To, D.C.M. Trtruhedron Ixtt., 2001, 42, 1343.
=+ OEt
OEt
-kPh OEt
=(OTMS Ph
1% Sc(OTfb
*
m a t s u . M.; Kurihayashi, M.; Koike, T. Synlett, 200Z, 1799.
Schmitt, A.; &&igJJ-
-
J
h
Eur. J. Org. Chan., 2001, 1169.
'\
1. MeOTf, DCM ,0"C 2,6-di-t-Bu-Py . aq N a H 0 3
*
57%
0
86% (61:39 kznscb)
'p
-A.;Draffen, A.G. J. Chem. Soc., Pmkin Truns. I, 2001, 2861.
81%
Compendium of Organic Synthetic Methods, Vol 11
646
1. 0
Section 365
2 ,Mn(Q abietate PhH, rt
Ph
0
Kulinkovlch.;Astashko, D.A.; Tyvorskii, V.I.; Ilyina, N.A. Synthesis, 2001, 1453.
TS
1. BCl3 , DCM , -78°C
Ph
2. pH 7 buffer
E
OMOM
H
n.,,E
Gasparski, C.M.; Hemnton, P.M.; Overma Tetrahedron Lett., 2000, 41, 943 1.
.
85%
+-)
.; Wolfe, J.P.
Ph
1. m ~ o H B F 3 - o ~
8 5 T ,90 nun
P hCH,C 0,H
* Ph
2. BF3eOEt2, DMFPCls rt,lh Balasuhramanian, S.;
L
Hollmann, C.; &&r&t&
Synth. Commun., 2000, 30, 469.
CO/II2 (80 bar) ,W"C, 2 d [Rh(cod)Cl]z, DCM
-
0
80%
GS
64% (1:l dr)
Tetruhedron, 2000, 56, 1685.
CAN ,MeOH , rt
n \
Ph
flair. V.; Nair, L.G.; Panicker, S.B.; Sheeha, V.; Augustine, A. Chem. Lett., 2000, 584.
5% Sc(OTf)3 , 10%Me011
,-),
..
\ /
/
N,
CHza2
Jain, R.P.; Bhattacharyya, A. Tetruhedron Lett., Z999,40, 5255.
OMe
647
Ether - Nitrile
Section 366
A
COzEt
COzEt
Br
2. K2C0,, acetone, rt
65~75%
0
n. P,V,; Krzeminski, M.P. Tetruhedron Lrtt., 1999, 40, 7879. Me&( OMe)SPh SnCl,
;-
* O M *.
62%
with TiCI4, RSPh is obtained in 86% Dronelles, L.; Silveira, C.C.; Wessjohann, L.A. Synthesis, 1999, 562.
. .
A
aJp,, CHO
, LiOH-H@
10%chiral phase transfer agent Bu,O, 4"C, 60 h
Arai.;Shirai, Y.; Ishida, T.;
e
P
h 80% (53% ee)
Tetrahedron, 1999, 55, 6375.
REVIEWS: "Epoxy Ketones as Versatile Building Blocks in Organic Synthesis," Lauret.C. Tetruhcdron Asynini., 2001, 12, 2359.
SECTION 366: ETHER, EPOXIDE, THIOETHER - NITRILE 10% Ti coinpkx, TMSCN
THF ,-5°C , 3 6 h 88% (76%ee) IIamashima, Y.; Kanai, M.;
'
Tetruhedron Lctt., 2001, 42, 691.
Lo*.
TMS-CN , h B r 3 ,CHzClz i
Ph
rt,3h
L Ph
O
A
c
CN 97% Bnndini, M.; Cozzi. P ,G; Melchione, P.; Umani-Ronchi. A. Tetruhedron Lctt., 200Z, 42, 2041.
648
Compendium of Organic Synthetic Methods, Vol 11
Section 366
-x
his-Ti-sakn complex (0.5%) MqSiCN,DCM,ld
A
Ph quant (66% ee) Ph CN Belokon, Y.N.; Green, B.; Ikonnikov, N.S.; North. M,; Persons, T.; Tararov, V.I. Tctruherlron,2001, 57, 771.
1. [DCM , EtZAlCl, rt , 2 h whohydrate phosphine oxide ligand]
PhCI10
-78°C 2. TMSCN , -60°C Kanai, M.; Hamashima, Y.;
96% (80% e e , S)
* Ph1 : N
>yny) '
Tetruhcdron Lett., 2000, 41, 2405.
Do
N
N
b '.
Th4SCN ,CIIc13 , -45"C,Ph 4 d * u , ( 9 1% ,% , e e )
Schaus, S.E.; Jacohsen. E& Org. Lett., 2000, 2, 1001.
A
TMSCN , 10% Ti(0i-Pr), , THF
K
TMSO,
-
10% chiral phosphine oxide Ph 85% (92% ee) -30"C, 36 h ' Hamashima, Y.; Kanai, M.; J. Am. Chem. Soc., 2000, 122, 7412. Ph
n
PhCIIO ,phase transfer catalyst NaOH
Makosza.; Pr.yborowski, J.;
d,
+q 0
Klajn, K.;Kwast, A. Synlett, 2000, 1773.
SePh
,,,,*I>*'
CI12=CIICN, Bu,SnII N B N , PhH , heat
I1IIIIl)
0
z
P
8
0
C02Me
Nimkar, K.S.;
-dfi 46% (2.1: 1 trunsxis)
cN
C1
--i
53% CO2Me Tetrulieclron,2000, 56, 5793.
+
CN
8
4 15%
C02Me
CN
Section 366
Ether - Nitrile
0
PhwcN 1. - 0 K O E I 10 eq\-(-)H
CN
Xie, R.L.;
5% Pd(PPh,), ,rt , Id 2.5%Gruhhs' catalyst, DCM CH,=CH, atmosphere, 1*d
649
ph6 81 X94%
Hauske.J.R.Tetruhedron Lett., 2000, 41, 10167.
N
M4SiCN , 3 M LiQO,/ether
Jinur.&
_".. ,
0.1 mPa
Ph
98%
Tetruheclrnn Lett., Z999, 40, 491.
TMSCN
0.1%chird Ti (salen) complex PhCHO
YTMS
86% ee
%,,,
CHzC12,rt , 1 d
Ph CN Belokon', Y.N.; Caveda-Cepas, S.; Green, B.; Ikonnikov, N.S.; Khrustalev, V.N.; Larichev, V.S.; Moscalenko, M.A.; North.; Orizu, C.; Tararov, V.I.; Tasinazzo, M.; Timofeeva, (3.1.; Yashkina, L.V. J. Am. Chetn. Snc., 1999, 121, 3968.
Testafeiri, L.; Santi, C. Eur. J. 0 1 - g . Chem., 1999, 797.
;-
PhCIIO
TMSCN ,Zr(Kpo,)z, DCM
90%
XO~S
reflux * 98% Ph Curini. M.; Epifano, F.; Marcotullio, M.C.; Rosati, 0.; Rossi, M. Synlett, Z999, 315. M q S i C N , 1d
b
1% chiral Ti salen complex
Ph Belokon. Y.N.; Green, B.; Ikonnikov, N.S.; Porth. M.; Tarapov, V.I. Tetruhcdron LEtt., 1999, 40, 8147.
quant (62% ee)
650
Section 367
Compendium of Organic Synthetic Methods, Vol 11
SECTION 367:
phx -
ETHER, EPOXIDE, THIOETHER ALKENE
Enol ethers are found in this section as well as alkenyl ethers.
EtOzC
C0,Et
Y,
PhI, 25°C , THF ,0.25 h InULYHCRCCHZOH]
[5% PdClz(PPh3)@uLi]
-
COzEt
89%
Bottex, M.; Cavicchioli, M.; Hartmann, B.; Monteiro, N.; J. Org. Chem., 2001, 66, 175.
MC7""
B IIOH, 5 % Pd(PPh3)4 10%P(O-TOl)s ,THF
&
100°C,3 d
0
Ph
noT
Ph
C7H15
69% Y. J. Org. Chem., 2001, 66, 270.
H Camacho, D.H.; Nakamura, I.; Saito, S.; -to.
3. E $AcOII 2 ,Pd(0Ac)Z*
& o
& m e c o e c h e a . ; Pkrez, E.; Solay, M. J. Org. Chem., 2001, 66, 564.
I n , H,O--EtOII ,rcflux
-
* pho40 h Ranu.; Dutta, J.; Guchhait, S.K. J. Org. Chem., 2001, 66, 5624. /
OH
90%
,Id
a t Pdz(dha)3
Lahmsse, J.-R.; Lhoste, P.; ~
O
U
D,. J. Org. Chetn., 2001, 66, 6634.
chiral pyrmlidho-oxazolidine PhOTf , PhH , Pdz(dha)3 i-PrzNEt, 75°C , 3 d
S . k ; Xie, D.; Fu, 2. J. Org. Chem., 2001, 66, 7240.
85% conversion (82% ee)
Ether - A k e n e
Section 367
65 1
(CII,=CH)*Sn ,Cu(0Ach * P 0, , M e C N , r t , 2 2 h Blouin. M, ; Frenette, R. J. Org. Chem., 2001, 66, 9043.
h
e
\ /
O
7 93%
oom ,chiral P,N-ligand
Pd$dha)3 ,i-Pr2NEt, PhH 70"C, 22 h
t
Gilhertson. S.R; Ru, Z. Org. Lett., 2001, 3, 161.
Bu,NEir, BSA
+
-
~~
105"C, 4 h
%
quant (94%ee)
B SA = (his-trimethylsily1)acetamide
10) 90%
(90
Smietana, M.; Mioskowski. C. Org. Lett., 2001, 3, 1037.
.
Gruhbs' oltalvst PhH
.&I
1.
M.-P,; Baylon, C.; Nolan, S.P.;
'
Org. Lett., 2001, 3, 1989.
10% AgC13
Me
014 IIoffmann-Riider, A,;
Org. Lett., 2001,3, 2537.
Br
Lee.;Lee, K.; Kim, S. Urg. Lett., 2001, 3, 3205.
74%
65 2
Compendium of Organic Synthetic Methods, Vol 11
Section 367
C02Me
Me0
A&.
DCM Tic& , -30°C , 3 h SiI’h2tBu
* & @ :$% 69e
ButP h2Si
Yadav.;Balanuragan, R. Org. Lett., 2001, 3 , 2717. 1.
PhCHO
mlO2s
/=Iy2
, DMAD, 25°C
*
42%
2. NEt3 , 6 5 T
lohnson.; Cheshire, D.R.; Stocks, M.J.; Thurston, V.T. Synbtt, 2001, 646.
c,ri 1 7 , (3rci2 ~ ,H,O ~ MqSiCl ,THF ,25”C, 1 d -
L
P
~
*
h
. K.:Morita, R.; Sakiunoto, S. Synlett, 2001,
*
1614.
1. Ph2CIIO€I, LIIMDS THF ,-78°C
Phozs -so2F’h
Ph
80%
+
2. Na/Hg, NaH2P04, M&II
Ph,rrco
A \
93% Cahianca, E.; Chkry, F.; pollin. P,; Cossu, S.; Pe Lucchi. 0. Synlett, 2001, 1962.
kx 0
OMe
C€12=€IIOEt , MgBr2=OEt2 ether, it, 15 min
*
d
0
O
E 90%
Mannucci, S. Tetrahedron L.ett., 2001, 42, 2023.
;-
2 qi-Bu3Al , DCE , 5 h
*Lp
Ph Cahrera, G.; Fiaschi, R.; Napolitano. E. Tetrahedron Lett., 2001, 42, 5867.
Ph
=
Me
BnOH , 10%P C I ( P P ~ ~ ) ~ 10% PhCOJ-I, dioxane , 100°C
Kadota, I.; Lutete, L.M.; Shibuya, A,; -to.
t
*
Ph
78%
OBn 96%
Y.Tetrahedron Lett., 2001, 42, 6207.
Ether - Alkene
Section 367
653
3. PhI, cat Pd(PPh3)4 NEt3 ,60"C
. & .; 011 -
-
Perez, E. Tetruheron Lett., 2001, 42, 3839.
p
-
COzMe
a t Pd(MtCN)2ClZ
-0 I
O
O"C, 0.5 h
o C O z M e
,."'
95%
T
C02Me
Kato. K.; Nishimura, A,; Yamamoto, Y.; Akita. H. Tetruhedron Lett., 2001, 42, 4203.
- -
-1
0.5 YhSeSePh , 3 h NaBHdEtOII ,reffux
C6l113
PhSe
c61I13
; Baroni, A.C.M.; LenardSo, E.J.; Gianeti, T.R.; IIurtado, G.R. Tetrulzerlron, 2001, 57, 4271.
4C0zMe
''
DABCO , 1 1 2 0 , rt , 2 h Kavichandran. S. Synth. Commun., 2001, 31, 1233.
COzEt
PhS
Cp2T4P(OEt3]z1 2 h reflux
Ph
+
P
h
a p e
d 62%
-ao
Rahim, Md.A.; Sasaki, H.; Saito, J.; Fujiwara, T.; T a k e d a . C h e m . Commun., 2001, 625.
A
1. LiC-KOR , T I I F , -95°C 2. B B u ~, 4 5 " C
3. HzO , -95°C OEt Tivola, P.B.; Deagostino, A.; M.C.: V-
86%
Clzern. Commun., 2001, 1536.
654
Compendium of Organic Synthetic Methods, Vol 11
4 PI1
Section 367
,Mn(OAc), , 4 0 T
[bmim] BF4, DCM
OH Bar, G.;
; Thomas, C.B. Chem. Cornmun., 2001, 1350.
50%
1. PhCCH , 2 eq MeMgCl 2. cat Pd(PPh3)2C12
Chaplin, J.II.;
B.L. Cltern. Cornmun., 2001, 1594.
1. PhCI-I=CH2,TiC14, DCM
2. KOII , rIZo
65% (1 :1 cis:trans) Kervredo, S.; Loiseau, M.; Lizzani-Cuvelier, L.; Duiiach. E. Chem. Commun., 2001, 2284. SiMqPh HSiMe2Ph , 3 % Pt complex 3% Py , S O T , 9 h W' .; Yamamoto, S.; Kawagishi, S.; Hiraoka, M.; Ikeda, S.; Minami, T.; Ito, S.; Yoshifuji, M. Chcm. Lett., 2001, 972.
Bu
2% Pd(PPh,), , 5 h * 4% P(OBu), 1. V.K.; Alonso, E.; Hynd, G . ; Lydon, K.M.; Palmer, M.J.; Porcelloni, M.; Studley, J.R. Angrw. Chem. In?. Ed., 2001, 40, 1430. 0
Ether - Alkene
Section 367
K
MQCO
t
H
u
5% [Pd~(dha)~].CHCl~ , 2h 20% dppe ,dioxane ,50°C
655
'0'0,
&If
OMe
85 %
Angew. Chern. In.t. Ed.,2001, 40,616.
Yoshida, M.;
s; Ishiwata, A.; Suzuki, T. Bull. Chern. SOC. Jpn., 2001, 74, 569.
uoB OTMSOTMS
-
92'4Tcb
E M , MS 4A,-78°C
20°F
COZEt
w; Eckardt, T. Angew. Chern. Int. Ed., 2000, 39,4343. K
70% (>98:2 EtZ)
1. CkZ,r(H)Q ,THF ,rt , 3 0 min 2. Se ,I.t, 30 min
=
72%
3. B a r , 5OoC, 1 h Hunnp.;Wang, J.-I-I. Synth. Cornniun., 2000, 30,307.
P h =
l.ZICp2(H)CI,DCM
L
Ph
*
2. PhzTez Liang, C.-G. Synth. Comr,zun., 2000, 30, 1737.
'OZEt
Se-Bn
ph*
TePh
67%
EtO,C BnCIIzCl.CH, toluene
CuI , DBU , aqTHF
Ph
hrcadl.; Cerichelli, G.; Chiuini, M.; De Giuseppe, S.; Marinelli, F. Tetruhedron Lett., 2000, 41,9195.
91% 0
656
Compendium of Organic Synthetic Methods, Vol 11
Section 367
MiGS.; Gao, W. Tetruhedron Lett., 2000, 41, 8933
Gogonas, E.P.; Uadiiaranodou. L.P. Tetruhedron Lett., 2000, 41, 9299.
e. r\L; I ~ u x M.; , Hoffmann-Roder, A. Tetruhedron Lett., 2000, 41, 9613.
2 eq M e 3 k C H C N , toluene
PhCOZMe
100"C,2d
Nan, Y.;Miao, 11.;
Org. Lett., 2000, 2 , 297.
Ph
HCtCCHzOH , THF Pd(PPh3hCb , t-BuOK reflux
Ph Monteiro, N.; Balmc, G . J. Org. Chem., 2000, 65, 3223.
MtO
CN
Section 367
T
M
657
Ether - Alkene
s
4 V
i-Bu
O
SnBu,
2.1 Ce(NB~4)2(N03)6,25°C* MeCN-DCM, MS 4A
yo 88%
i-B u
Chen, C.; M ~ ~ L J L J.&Org. Chem., 2000, 65, 3252.
Younr.;Jung, L-j.; Cheng, K.-m. Tetruhedron Lett., 2000, 42, 3411.
Pale.;Chuche, J. Eur. J.
Org. Chent., 2000, 1019.
LiCl , Pd( PP h3)4
Ph
N
75%
Schaus, J.V.; Panek. J.S. Org. Lett., 2000, 2, 469. Ph-<
01I
Labrosse,
Pd2(dha), ,R-MeO-Biphep 25°C
J.-K.;Lhoste, P.; &OU.
PhSh PCarter, D.S.; Van Vr-
Pi1
99% (87% ee)
D, Org. h t t . , 2000, 2 , 527. MqSiCII=N2 ,DCE , 84°C 5% FeBr2PPh3, 2 h
Org. Lett., 2000, 2, 1303.
88% (85:15 dr)
SiMq
SPh
658
Compendium of Organic Synthetic Methods, Vol 11
Section 367
1. c o j m ) , SiMe3
2. toluene, heat, 12 h
70%
SiMe3
Dolaine, R.;
Org. Lett., 2000, 2, 1753.
Y
+do
RhAO-oct), , hexanes reflux
oms
83%
oms
-om
b v i e s . H . m; Calvo, R.L.; Townsend, R.J.; Ren, P.; Churchill, R.M. J. Org. Chcnr., 2000, 65, 4261.
0
PhOTf , 5 % Pd(dhah*dha, PhtI , 5 d
15% chiral P-conhining oxazoline ligand 81% (96% ee) i-Pr2NEt, 70°C IIashimoto.;Hone, Y . ;Hayashi, M.; Saigo, K. Tefruhedron A s y m . , 2000, 11, 2205.
OH
Anwar, U.; QggJ+;
Sridharan, V. Chern. Cornntun., 2000, 933.
P.T.; Nocanda, X.W. J. Chenz. Soc., Perkin Truns. 1, ZOUU, 1331.
Ether - Alkene
Section 367
659
3. 2.5 eq [(allyl)PdCl], ark. S.E.; Neuville, L. Org. Lett., 2000, 2, 3221.
1. PhzCuLi, TIiPOCEizCHO ZnC1, 2. TsOH ,THF MBndez-Andino, J.; paouette. L.4. Org. Lett., 2000, 2, 4095.
i-PICHO a t TMSOTf
SiMe2Ph
MeOzC
i-Pr
pha
86% (9; 1 yyn:anti)
h a n g , H.; Panek. J.S. J. Am. Chem. Soc., 2000, 122, 9836.
Clay, miaowaves , 6 inm
ph
85%
Ph
Meshrdm.; . , Sekhar, K.C.; Ganesh, Y.S.S.; Yadav, J.S. Synlett, 2000, 1273.
-
-Yk€i, -
cs1-I11
do C5Wl
0.7 M
MeOK
5% Pd(OAch, 2% TDMPP rt , 5.5 d Me02C * TDMPP = tris-( 2,6-dimethoxyphenyl)-phosphine Trost. B.M.; Frontier, A.J. J. Am. Chem. Soc., 2000,122, 11727. Ph,P=CHCO,Et, 90 S
61%
~ C
(20:80 E:Z) CHCOzEt ; Reddy, M.M.; Srinivas, D.; Yadav, J.S. Tetruhedron Lett., 1999, 49, 165. microwaves
660
Section 367
Compendium of Organic Synthetic Methods, Vol 11
fio2yT 2 9 PtCI2, MeOH , 2 d
Ph0,S
,,,MI
OMe
Ph Ph Mkndez, M.; Muiioz, M.P.; Echavruren, A.M. J. Am. Chem. SOC.,2000, 122, 11549.
EtCIIO, BF3.OEt2
70% (70:30 cis:trans)
& x e d E t Regis, D.; Afonso, M.M.; Galindo, A.;
.
.
Tetruhedron Lett., 2000, 41, 6781.
63% (11.8, DZ)
31%
Ishino.Y.;Kita, Y.; Maekawa, H.; Ohno, T.; Yamasaki, Y.; Miyata, Y.; Tetmherlron &It., 1999, 40, 1349.
vph Et,SiII, PBu3 cr.10 Tang, X.-Q.;
Ph
Ni(cod), , 4 5 T
&
J. Am. Chem. SOC., 1999, 121, 6098.
5%-RuCl(c0d)C.jMe.j OM *
30 min , rt OH at 80°C for 1 h, ohtain 80% of ally1 ether derivative Dtrien, S.; Ropartz, L.; Le Paih, J.; J. Org. Chem., 1999, 64, 3524.
80%
Section 367
Ether - Alkene
66 1
CkTiMe2, toluene ph+ 76% 75-80°C Dollinger, L.M.; Ndakala, A.J.; Hashernzadeh, M.; Wang, G.; Wang, Y.; Martinez, I.; Arcari, J.T.; Galluzzo, D.J.; &well. hB. J. Org. Chem., Z999,64, 7074.
PCU,, 2
KI, DMA
fi
*
25”C, 18 h
92%
0
ria, E. J. Org. Chem., 1999,64, 7687.
HC03-, MeOH *
+phyPha OMe
ON”KNH2 0 2576 ;- 1‘ Osterle, C.G. J. Org. Chem., 1999,64, 7756.
75%
PhJ+ BFd- , K2C03 MeCN , GOOC, 3 h
76%
b;mt . . S . - k Baik, T.-G.; Kulak, A.N. Synlerr, 1999,324. CH2-(Znlh, 4 eq Tic12 , 4 h C7H15
8 eq TMEDA, TIIF, 25°C
OEt
LOEt 75%
C7H15
MdtSUhrlTd.; . . . . IJkai, K.; Mizuno, T.; Utimoto, K. Chem. Lett., Z999,825. Ph ;-
=
1. Cp2Zr(H)Cl , THF
* P h m s p h 2. PhSCl Zhong, P.; Guo, W.-r. Org. Prep. Proceed. Int., 1999,31, 201.
85%
(CH20), , toluene, reflux, 1 h Ph P
T
3\0
/
Qkuma.; TanAa, Y.; Shuzui, 1.; Shioji, K. Heterocycles, 1999,50, 125.
90%
Section 368
Compendium of Organic Synthetic Methods, Vol 11
662
I-Iilagenkamp, R.; Brogan, J.B.;
3.P-TsOH, PhH ,80°C
Heterocycles, 1999, 51, 1073.
Related Methods:
SECTION 368:
22%
Section 180A (Protection of Ketones)
HALIDE, SULFONATE - HALIDE, SULFONATE
+;
IIalocyclopropanations are found in Section 74F (Alkyls from Alkenes). BrZ, [bmim] Br
+
M9
M
%
Br A
%
ionic liquid medium
Br
Br
Et
(>99
Et
0
e- , Et,NI, NEt,-THF CHlCl2, rt
e
Kobayashi, S.; Sawaguchi, M.; Ayuha, S.; Fukuhara, T.;
PhCHO
1) 95%
0;
Oiappe. C.; Capraro, D.; Conte, V.; Pieraccini, D. Org. Lett., 200Z, 3, 1061.
90%
,* .
Synlett, 2001, 1938.
PhCH=CHZ, BC13 , CHZCl2 Phu
p
h
9wo (53:47RR(SS):RS(SR) Kahalka. G.W.; Wu, Z.; Hu, Y. Tetruhedron Zxtt., 2001, 42, 5793.
CAN, KBr , H z 0 , DCM rt ,20min
BuyB
Br Nalr.;Panicker, S.B.; Augustine, A.; George, T.G.; Thomas, S . ; Vairamani, M. Tetruherlron, 2001, 57, 7417.
82%
Section 371
Halide - Alkene
SECTION 369:
663
HALIDE, SULFONATE - KETONE
Yorimitsu, H.; Shinokuho, €1.; Matsuhara, S.; J. Org. Chem., 2001, 66, 7776.
; Omoto, K.;
6 e q K g 0 3 , S e q B r 2* u
r
+
0°C , 5 h
I&
97%
Zhang, W.-C.; Li. C.-J, J. Org. Chem., 2000, 65, 5831. 1. LDA, TfIF 2.TsCl
Ph
*
Ph
a
61%
Brummond.,Gesenherg, K.D. Tetruhedron Lett., 1999, 40, 2231.
A
Ph
1. IIMB ,MeCN ,reflux 2. SiiIT2,THF ,rt
* PhL
I
82%
HNIB = (hydroxy-p-nitrobenznesulfony1oxy)benune Lee. J.C.; Jin, Y.S. Synth. Cornmun., 1999, 2Y, 2769.
SECTION 370:
-
HALIDE, SULFONATE NITRILE NO ADDITIONAL EXAMPLES
SECTION 371:
Bu
Dahdo
=
HALIDE, SULFONATE - ALKENE
SnBu3
1. CpzZr(H)CI ,THF ,rt 2.2.15 eq I2 , TfIF ,rt
*
BuH1 78%
H
I
I ; Dahdouh, V.B.; Baroni, A.C.M. J. Am. Chem. Soc., 2001, 123, 9694.
664
Compendium of Organic Synthetic Methods, Vol 11
Section 371
C7H15
OAC
1.5% Pd(OAc)z , 4 0 T 2.5 eq LiBr , AcOH , 25 h acetone
Horviith, A.;
-
J. Org. Chem., 2001, 66, 8120.
+lJ
C5H1 1
85 %
SWe3 1.2.5 eq CPZzZr(WC1
ITIF, 53°C 2.12 , DCM ,It
3. MeZnCl , Pd(PPh,)4-THF 4.12 ,DCM Arefolov, A,; Langille, N.F.;
50~95~75%
Org. Lett., 2001, 3, 3281. 1. Zn,DMAC
F Liu, Q.;
Ph
2.PhI,CuBr,rt Ir cat Pd(PPh3)4 , 4 h DMAC Tetrulzedron Lett., 2000, 41, 8045.
A/
Ph
76 X 74%
AccC1 , ZnClz/SiOz ,DCE
3 0 T ,1 h
-+
PhL
M
e
91%
KKodomari. M.; Nagaoka, T.; Furusawa, Y. Tetrahedron k i t . , 2001, 42, 3105.
Bu
=
Su, M.; Yu, W.;
SPh
TMSBr ,CH2Q2, -40°C MaH,1h
- Buq-sph
Tetruhedron Lxtt., 2001, 42, 3771.
NBS , K-10 Monhnorillonite MeOH
99%
Br
Br 60%
665
Halide - Alkene
Section 371
V.G : Balenkova, E.S. Synthesis, 2001, 2081
Shastin, A.V.; Korotchenko, N.; =nko.
K:
AczO , MgBq ,T H F
CqMe Ph+
*
It,lh
Ph
86% (100%Z)
handran . S.; Synth. Corrlnzun, 2001, 31, 2059.
M
cetylMe,NBr, DCM , KzCO3 0°C-
It
=
Chem. h t t . , 2001, 290.
Bose, G.; Barua, P.M.B.; Chaudhuri, M.K.; Kalita, D.;
Bu
NCS
*
70%
&Br
&Bu
Br 82%
IIoshl.;Shirakawa, K. Tetruhedron Lett., 2000, 41, 2595. 1. CCI3COzII, Cl3COzNa DMF ,35"C
2. AcZO, 25°C 3. Zn , AcOM ,6O"C 92% C1 Wane.;Campagna, S.; Xu, G.; Pierce, M.E.; Fortunak, J.M.; Confalone, P.N. Tetruhedron Lett., 2000, 41, 4007. CHCb ,6O"C, 34 h BF4;.T-
. .
/-/I
Fujita, M.; Gronheid, R . ; Lodder, G. Tetruhedron I L K , 2000, 41, 5125.
93%
666
Compendium of Organic Synthetic Methods, Vol 11
<
Yu, W.;
=
o z 3 1 r , MeOH, DCM ,-40°C 89%
J. Am. Chem. Soc., 2000, 122, 9840.
0
Section 371
CF3COOH
Br
83%
MouEhamlr.K.; Mezgueldi, B.; Atmani, A.; Mestdagh, 11.; Rolando, C. Tetruhedron Lett., 1999, 40, 59.
1. SnQz , NEb ,CHglZ, rt 2.12 COzB n Kitagawa, 0.; Suzuki, T.; Fujiwara, H.;
(k.
1. DMD, acebne ,rt 2. NaBr , Amherlyst-15 1t,12h ; Sperandio, A.
96%
Tetruhedron k t t . , 1999, 40, 5889.
2 eq SmI, C7H15
*
t
AI
C7H15
88% (94:6 Z E )
I
Qncellcin.
J.K; Bernad, P.L.; Pkrez-Andrks, J.A. Angew. Chem. Int. Ed., 1999, 38, 2384. 1. dilauryl peroxide, PhH ,reflux 2 . 5 eqEtSOZN3, PhCl 0
dilauryl peroxide, 100°C
80% (74:26 exo:endo) N3 Huanp.;Wang, J.-H.; Yang, D.-Y. J. Chern. Soc., Perkin Truns. I , 1999, 673.
667
Ketone - Ketone
Section 372
Br+(collidine)2 PF6-, DCM C7H, 5
* C7H15
-40°C
C02Me 92%
Roussedu.; . . Marie, J.-X. Synth. Commun., 1999, 29, 3705. REVIEWS:
"AnEfficient New Methodology For The Synthesis Of 1-Functionalizd-2-Halo-2-Alkenes Via Hydrohalogentation Reaction Of Electron-Deficient Allenes," Ma.;Li, L. Synlett, 2001, 1206.
SECTION 372:
-
KETONE KETONE
+(y-c;? @ \ /
$
$:
OMe
PIFA = phenylbdine (In)bis(trif1uororlcetate)
85% Arisawa, M.; Ramesh, N.G.; Nakajima, M.; Tohma, H.; fita. Y. J. Org. Chem., 2001, 66, 59.
0
Ph
'''h
TMSO chir d qua ternary ,10h
ammonium s a t 50% KOH ,toluene -20°C
Ph
h p$+
81% (99% ee)
Zhang, F.-Y.; h s y , L , L Org. Lett., 2001, 3, 639.
Pei, T.;
J. Am. Chent. SOC.,2001, I23, 11290.
% Ph
9% (90% eel
668
Compendium of Organic Synthetic Methods, Vol 11
Section 372
01-1
l.
2.
, 2% PdC12(PPh 1% CUI, NEt3, heat ==J-Ph
NC-@H
Ph
CN
y+
20%
88% I-
Me
Braun, R.U.; Zcitler, K.; Miiller, T.J.T. Org. Lett., 2001, 3, 3297.
1.5 “(1
rcc, DCM L
84%
rt, 10h
Ren, S.-K.; Wang, F.; Dou, 11.-N.; Fan, C.-A,; IIc, L.; Song, Z.-L.; Xin, W.-J.; Li, D.-R.; Jia, 2001, 2384.
Y.-X.; Li, X.; Tu. Y.O. Synthesis,
, V O C I ~MS , 4A
Ph
, EtOII , DCM
=3<0TMS-75°C-
63%
-30°C
Kurihara. M.;Hayashi, T.; Miyata, N. Clieiiz. Leu., 2001, 1324.
=
I%
11:
.
J. Aim
I’h
(CU*)RUO~(CO~CF~) , MeCN
*
0 . 2 TFA, rt
+T
PI1
0
. W.-Y,; Chan, P . 4 4 . ; Chcng, W.-C.; Peng, S.-M.; Lau, K.-C.; Li, W.-K. Clrc~iir. 122, 11380.
’._
,
.
98%
u. Soc., 20U0,
AN
111
DMF, rt , 8h
Baek, €1.; Lee, S.J.; Yno. B.W. ; KO, J.J.; Tetruhedroir Ldt., 2000, 41, 8097.
-
4rfi 62%
PI1
; Kim. J.1-I.
0
Section 374
Ketone - Alkene
669
acetone ,ZnCl,*Et,NII r-BuOH , PhH ,rt , 3 d Br Nevar, N.M.;
64%
Br
Synthesis, 2000, 1259.
REVIEWS: ; Ruhinova, I.L.; Akhrem, A.A.
"Chemistry of 2-Acylcycloalkane-l,3-diones," Cheni. RL'v., 1999, YY, 1047.
SECTION 373:
KETONE - NITRILE 0
II
1 . 0 3 , Me011 ,M q S
A /CN
2. TsOH
Flemine. F.F.; Huang, A.; Sharief, V.A.; Pu, Y. J. Org. Chent., 1999, 64, 2830.
SECTION 374:
KETONE - ALKENE
For the oxidation of allylic alcohols to alkene ketones, from Alcohols and Phenols)
see
For the oxidation of allylic methylene groups (C=C-CHz Section 170 (Ketones from Alkyls and Methylenes).
Section 168 (Ketones
4
C=C-C=O), see
For the alkylation of alkene ketones, also see Section 177 (Ketones from Ketones) and for conjugate alkylations see Section 74E (Alkyls form Alkenes).
.
.
u i a r u ; Leconte, S.; Bknard, A,; Brown, E. Synbtt, 2001, 147.
Section 374
Compendium of Organic Synthetic Methods, Vol 11
670
C02i-Pr 0.1 yh(oTf), ,40"C DCM, MS 3 A . 96 h
C02i-Pr
eP
99% (34:GG syn:unti)
-Abraham, . .
Bu
-
L. Org. Lett., 2001, 3, 49.
=
O (T
1.
Ph
)= Cr(CO),
Me0
2. Ce(IV) 3. PhBr , dioxane p w
0
(mf)
-
Ph
/
66~98%
Ph
0
Davies, M.W.; Johnson, C.N.; w v . J . P . A J. Org. Chem., 2001, 66, 3525. 1. B-0-
U
Q
C
-&
P ,h-78"C, 5 h
Y
0
L?
2. PhIi, SiO, ,reflux
74%
Shlndo.;Sato, Y.; Shishido, K. J. Org. Chem., 2001, 66, 7818.
@
N B S , €40,THF
1.1
H2S04,rt,5min
OMe Kim, D.W.; Choi, H.Y.; Lee, K.-J.;
H
TMSO
Arisawa, M.; Akamatsu, K.;
0
, GaC13
2. R .
I
80%
Org. Lxtt., 2001, 3 , 445.
1. TMS-
CO2Et
,@
-ij, COzEt
'
Org. Lett., 2001, 3, 789.
74%
Ketone - Alkene
Section 374
67 1
2.5%Co2(C0)8 ,30a&nCO DCM,130"C, 18 h
TIPS
0
Son, S.U.; Yoon, Y.A.; Choi, D.S.; Park, J.K.; Kim, B.M.; Org. Lett., 2001, 3, 1065.
75%
Ph I
5% Ira(CO)(PPh3)2 CO, xylene , 120°C
B nOzC
c
@ 86%
Ph
Shih,lta.; Yamashita, K.; Ishida, If.; Takagi, K. Org. Lett., 2001, 3 , 1217.
Ph
Jja mi. . .
11
Ph
i-PrNO, MtC ,DBU, N rt
0
; Bosica, G . ; Fiorini, D.; Gil, M.V.; petri .
Org. Lett., 2001, 3, 1265.
5% Pd catalyst, 130°C 2 eq Nu$JOAc , DMF
MeCN, H20.16 h Br Hiigenauer, K.;
*Q /
72%
Org. L ~ t t . 2001, , 3, 1495.
c s CLi Ph
Me1 TMEDA , ether *
Ph%
50%
Murai.; Mutoh, Y.; Kato, S. Org. LEtt., 2001, 3, 1993.
77%
672
Compendium of Organic Synthetic Methods, Vol 11
Section 374
MtCN ,30"C
CO atmsphere ,reflux , 1d
Cvdns.; ' . . Rohinson,
(7 : J.E. J. Am. Chem. SOC., 2001, 123, 4609.
1) 88 X87%
MeCN, 80°C 2.1NHC1,DCM Martinez, S.; Suhrez-Sohrino, A.L.; Tomis, M. J. Am. Chem. SOC.,2001, 123, 11113.
;-
cat rRh(dppe)zlz(BF4)2
-
CIOH21
MtCN ,100"C 67%
Tanaka, K.; Fu. G . C , J. Am. Chem. SOC., 2001, 123, 11492.
&
*
,co,1 atm
-0Ac
/
MtCN , 8 0 T , 4 h Chatani. N.; Kamitani, A.; Oshita, M.; Fukumoto, Y.; Murai. S. J . Am. Clzem. SOC.,2001, 123, 12686.
-
5% Co catalyst, CO ,70°C
Ts-
N
L
n f F , 1d
n
-
a
80%
0
84% Comely, A.C.; Gibson. S.L; Stevenazzi, A.; Males, N.J. Tetmhedmn Z ~ t t .2001, , 42, 1183.
Section 374
Ketone - Alkene
673
1.
4 eq Li naphth ,-78°C
99%
2. BnBr , 2 0 h 3. P-TSOH, PhH ,reflux
Tai, C.-L.; Ly, T.W.; Wu, J.-D.; Shia, K.-S.; Liu. H.-J,Synlett,2001, 214.
cogt 42% (>98:2 fruns:cir)
NaH, TIIF, 55°C PW3
OEt
Lancer.; Kracke, B. Synlett, 2001, 1790.
Pd(0Ac)z , MeCN , 1 0 0 min
COzMe
rt
79%
Tetruhedron LEtt., 200Z, 42, 1555.
2 . 2 q Co2(CO), , DMSO CHZ=CH,, 110°C , 4 d
*
Rausch, B.J.; Gleiter. RL Tetruherlron Lett., 200Z, 42, 1651.
Hanzawa.;Kakuuchi, A.; Yahe, M.; Narita, K.; Tahuchi, N.; Tetruhedron Lett., 200Z, 42, 1737.
1 ~ 2 . E:Z 4
U
Section 374
Compendium of Organic Synthetic Methods, Vol 11
674
1. CodCD), , MS 4A
2. M%N-0, It
b/J
OH Blanco-Urgeiti, J.; Casmubios, L.; Domhguez, G.; Tetruhedron k t t . , 2001, 42, 3315.
,DMF,6O0C,30he
OH
60% (I: 1 ciF:&m)
&$(
10%[CpRu(MdN)3] PF6 71%
Yoshida, M.; Sugimotot, K.; U T e t r u h e d r o n Lett., 2001, 42, 3877.
1
l,proline,DMF,rt,6h 2.45 h ,
3. HZO 4. PhH , reflux ,p-TsOH , 2 h Rajagopal, D.; Narayanan, R.;-athan.
70% (76% ee) S, Tetruhedron Lett., 2001, 42, 4887.
acetaphenone , MeOH ,18 h
+ PhCH=CHBz 98% natural phosphate, N&O3 Sehti. S.; Solhy, A,; Tahir, R.; Boulaajaj, S.; Mavoral. J.A.; Fraile, I.M.; Kossir, A.; Oumimoun, H. Tetruhedron Lett., 2001, 42, 7953. PhfflO
. .* . IShlZdkl.; Iwahllra, K.; Niimi, Y.; Satoh, H.;
H
Tetruhedron, 2001, 57, 2729.
Section 374
Ketone - Alkene
675
0 1. CojCO), ,DCM
*
2.NMO,OoC+ rt
d
I,ovelv.; Seshadri, H.
7
3
%
Synth. Cornniitn., 2001, 31, 2479.
Ni(cod), , TMSCl CO , toluene
o-rlGarcia-Gcirnez, G.; Moret6. J.M. Eur. J. Org. Chem., 2001, 1359.
0 HC'
AlCl:, ,IC1,O"C
1.5
DCM ,45 min
Sha. C.-K.; Lee, F.-C.; Lin, 11.-H. Chem. Cornmun., 2001, 39. CH2=C=CH2, 5 % Ni(cod), Ph
SnMe:,
Shlrakawa.; Nakao, Y.;
6"
toluene , 1.5 h
*
64%
Ph
Chem. Commun., 2001, 263.
, Gruhhd catalyst II
DCM ,45"C, 6 h
Randl, S.: Connon, S.J.;
83%
'
Chem. Continun., 2001, 1796.
86%
Section 374
Compendium of Organic Synthetic Methods, Vol 11
676
collodial cobalt , 5 am CO EtOz
TI-IF, 130°C , 10 h
97% Kim, S.-W.; Son, S.U.; Lee, S.S.; Hveon. T.: Chune. Y .K. Chem. Commun., 200Z, 2212.
L
*wo
cat C ~ ~ ( C O ~ ( ~ ,~toluene CII)
P -/h 0
P
20 atm CO ,95"C
h
70%
Ph
Sueihara. T.; Wakahayashi, A.; Takao, H.; Imagawa, H.; Nishizawa, M. Chent. Commun., 2001, 2456.
P&rez-Serrano,L.; Casmuhios, L.; Dominguez, G.; P&rez-C&&d Chem. Commun., 2001, 2602.
4
siMe3
3 eq mcpha , 4 eq H 2 0 , DCM
OMe
3 eq TiI4, PhCH(0Me)Z -78°C -+ -20°C
Hayakawa, R.; Makino, H.; m
t - p 1 0 SiMeIPh
u
Am
. M.Chem. Lett., 200Z,756.
'0
Me0
65%
eq AcOII , toluene, 70"C, 12 h
5% [RhCKm)zlz Yamane, M.; Amemiya, T.; Narasaka. K. Chcnr. Leff., 200Z, 1210.
77%
677
Ketone - Akene
Section 374
u; Watanabe, T. Heterocycles, 2001, 54, 73.
79% (38%de) 0
0-
,TCE, 60°C ,5
0
I Ph
,cat[Rh(0)2C12]
Wentler. P.& Gamber, G.G.; Scanio, M.J.C. Angew. Chetn. Int. Ed., 2001, 40, 3895.
J-Lc1
a
82%
toluene , DBU , 1 d C02Me
MLO~C Lavoisier-Gallo, T.; Charonnet, E.; Pons, J.-M.; Rajzman, M.; Faure, R.; &drip uez. J. Chetii. Eur. J., 2001, 7, 1056.
CIIO MtO2CCICC02Me 20% Py ,DME
NO2 Nair. V.; Sreekanth, A.R.; Vinod, A.IJ. Org. Lett., 200Z, 3, 3495.
72%
678
Section 374
Compendium of Organic Synthetic Methods, Vol 11
7 0
,LiBr,DMFM Q oe)
,01H
Y /
10% CpRu(NCMeh+PF,-
CdI 13
15% SnC14*5H 2 0 , 60°C MeO-- r L C H O
W
t
Po
\
Br
Br
52%
20%
Trost.;Pinkerton, A.B. J. Am. Chem. Soc., 2000, 122, 8081. PhOTF ,chiral Pd catalyst i-Pr2NEt, TIIF, 50"C, 2 d
=
m P h
87% (85% ee)
0
Ogasawara, M.;Yoshida, K.; IIavashi. T, Heterocycles, 2000, 52, 195. cat Co ,charcoal, 18 h
E D 2C
0
20 atm CO, 130°C ,THF
Son, S.U.; Lee, S.i.; ChunpAngew. Chenz. Int. Ed., 2000, 39, 4158.
98%
MeO
Ph
OMe PhOCH,THF
reflux
0 71%
0
mushroom tyrosinase , 6 h phosphate buffer (pH 6.8)
Me
Me Gupta, R.; Mukh eriee. R. Tetruhedron Lett., 2000, 41, 7763.
85%
Me
Section 374
Ketone - Akene
,80°c
679
phT+ phT /
1% (Rh(cod)(MeFh2P)z]OTf MeCN , sealed tuhe , 19 h
Ph Muraoka, T.; M&&&
0 (55
:
0 45) quant
; Itoh, K. Tetmhedi-on Lett., 2000, 41, 8807.
xlr=
Co/silica (9-10% CO wt%) 20 atm CO 130°C 6 5 h , THF
D-
Kim, S.-W.; Son, S.U.; Lee, S.I.; Hveon. T,; Chung, Y.K. J . Aiii. Chein. Snc., 2000, 122, 1550.
JO 1111111111
Park, S.-B.;
96%
0.1 Pd(0Ac)z. 2 eq Py toluene, S O T , O2 MS4A,4h
Org. Lett., 2000, 2, 147.
1. (qz-C31&)Ti(OiPr)2
0
2. S-BuOH
\ GH11
62% (93%ee)
Urahe, 13.; Hideura, D.;
Org. Lett., 2000, 2, 381.
Li , t-BuCHO
4,4-di-t-hutyl-hiphenyl * -hP Hashernzodeh, M.;
45% Tetmhedron Lett., 2000, 41, 1855, 1859.
680
Section 374
Compendium of Organic Synthetic Methods, Vol 11
Fe,(C0),2
1. B u N H ~ ,THF 2. C~M,,ClCII
*
3. CUCl2'2 H20 Rameshkumar, C.;
fil
61%
( 3 1 1
Tetruhedron Lett., 2000, 41,2719.
.,
Pbrez-Seinno, L.; Blanco-Urgoiti, J.; Casllrrubios, L.; Dominguez, (3-;. J. Org. Clic~111.,2000, 65, 3513.
0.05M, DME ,60%CyNII2 10% [CO,(CO),21 , co ,70"C 18 h
92% L.V.R. Angew. Clirrrr. hit. Ed., 2000, 3Y, 3676.
t
hmcine N-oxide , DME -60"C, 5 d 63% (11:89 er) W.L; Lindsay, D.M.; Rankin, E.M.; Scott, J.S.; Watson, S.P. Tetruheilron Lxtt., 2000, 41,3229.
PhCIIO
a
11
,TiCb,DCM
It, I d
Ph
I.i.LL; Gao, J.; We, I-I.-X.; Enright, M. Org. LEtt., 2000, 2, 617
92% L
l
Section 374
Ketone - Alkene
68 1
*gD H
m
o
w
4
, 3 atm CO ,THF
e
[RUCI~(CO>,]~, NEG , 120°C, 5 h
0
Morisaki, Y.; Kondc>.T.: Mitsudo. T .-a. Org. Lett., 2000, 2, 949. 0
80% (100% em)
1. CF,(CF35-C,€I&kCl 2. H202
86%
3. Na2S205 4. fluorous extraction Crich.;Barha, G.R. Org. Lett., 2000, 2, 989.
IICrCCII20Me , 0 S M DCE
-+ -(Lo
0.5% [Rh(c0)~Cl]2,80"CII P
92%
Wender.; Dyckman, A.J.; Husfeld, C.O.; Scanio, M.J.C. Org. Lett., 2000, 2 , 1609.
Bartoll.;Bcllucci, M.C.; Petrini, M.; Org. Lrrtt., 2000, 2, 1791.
; Samhri, L.; Torregiani, E.
2 eq PhCICH ,30 atm CO
5% CO~(CO),, 130°C D C M , 18h
-
0
Son, S.U.; Choi, D.S.; m c . Y.K.; Lee, S.-G. Org. k t t . , 2000, 2, 2097.
68%
682
Compendium of Organic Synthetic Methods, Vol 11
4
&
Pd(dba)z, MeCN ,50"C
Ph
*
20 h
Section 374
98%
Ph Okumoto.; Jinnai, T.; Shimizu, H.; Harada, Y.; Mishima, H.; Suzuki, A. Synlett., 2000, 629. 0.02 DME ,35% CoZ(CO), 1.5 CyNHz , 60°C
EtOzC
w
Nz atmovheE
EtOzC
80%
Okumoto. H.; Nishihara, S.; Yamamoto, S.; Hino, H.; Nozawa, A.; Suzuki, A. Synlett, 2000, 99 1.
C,H,
=
SeEt
1. C p g l c l , DCM 2. BzCl , 15% CuBr-SMe,
*
82%
GH7 .Synthesis, 2000, 789. Suwa, T.; Sugiyama, E.; Shibata, I.; Baha. 4
160°C. Ph20, 1 h
H
*
76% 0
Ovaska. T.V,; Roses, J.B. Org. Lett., 2000, 2, 2361.
- ,Me !02C'
u
JeonL..; Sung, B.S.;
Me
3% [RhCl(CD)z] ,9%S-BINAP ML92 12% AgOTf, 2 a h n C 0 , TIIF 30"C, 20 h
MeO-C'
91%(62%ee) H Choi, Y.K. J. Am. Cheni. SOC.,2000, 122, 6771. PhCIIO ,In/InCI,, rt
*
aq TIIF Kmg, S.; Jang, T.-S.; Keum, G.; Kang, S.B.; Han, S.-Y.;
phT 0
69%
Org. Lett., 2000, 2, 3615.
Section 374
Ketone - Alkene
"'2&T-
C o d 2
z;:
EQ& Hayashi, M.; ; Ymamoto, Y.; Usuki, J.; Angew. Chem. Int. Ed., 2000, 39, 631.
683
Et0,C
909i
15 atmCO, 110 atmCI12=CI12, 85°C
P h =
3% cO~(CO),,[P(oPh3)),41 h
Jeong. N.; Hwang, S.H. Angew. Chem. Znt. Ed., 2000, 39, 636.
2 eq o-iodoxybenzol: acid 65°C. 10 h
eih
(1 Nicolaou. K.C.; Zhong, Y.L.; Baran, P.S. J . Am. Chem. SOC., 2000, 122, 7596.
210% q PPd(OAc), h I , S O T,20% , 12 h ,PPh3 DMF
* Ph
2) 76%
2 eq Nu4NCI , 2 e q i-Pr2NEt
I,arock.; Reddy, Ch.K. Orx. Lett., 2000, 2, 3325.
"XBu 1.4 q t-BuLi , -78°C
Bu
Bu
2. CO, , -78°C
+
-30°C
u; Song, Q . 1. Org. Cheiit., 2000, 65, 9157.
A
Ph ;-
I
.
.
A
Bu
*
Bu
70% Bu
,soT,o.~~ SnMe3
S11Me3
5% Ni(codh, toluene 0 72% Nakao, Y.; Yoshida, H.; J. Am. Chem. Soc., 2000, 122, 9030.
Section 374
Coinpendium of Organic Synthetic Methods, Vol 11
684
0
, 3 0 atm CO, 110°C
5% Coz(Co), , D C M , 18 h 80% Son, S.tJ.;
; Lee, S.-G. J. Org. Chem., 2000, 65, 6142.
PhCsCH , Coz(CO)6, toluene pulegone phosphin&B H, complex 50°C
Verdaguer, X.; Moyano, A,; lhk&Jf& Riv&; J. Am. Cheni. SQC., 2000, 122, 10242.
1.
€1 99%(99%ee) Maestro, M.A.; Mahia, J.
y,
solvent free , KOH
rt,3 h 2. 3M HCl
Miyamoto, 11.; Kanetaka, S.; Tanaka, K.; Yoshizawa, K.; Toyota, S.; Toda. F, Chenz. Len., 2000, 888.
L
Ph
Mukaivama.
1. LDA ,TIIF,-78°C
Ph 2. Ph(Cl)S=Nt-Bu, THF ,-78°C* PhL
1; Matsuo, J.-i.;
P
h
95%
Kitagawa, H. Chem. Lett., 2000, 1250.
,ultrasound
COZ(CQ )6
NEt, ,toluene, 15 min I
H
99%
Ford, J.G.; J ~ K W.J.; . Kirk, G.G.; Lindsay, D.M.; Middlemiss, D. Synlett, 2000, 1415.
Ketone - Akene
Section 374
-3
Ph
1. TMSC(Li)N2, TIIF -78°C- rt
*
2. 1NHC1,O"C
0
. ..
Sakai, A.;
685
'
82%
Tetruhedron Lett., 2000, 41, 6859.
Brown, D.S.; Campbell, E.; Kern. W.J.; Lindsay, D.M.; Morrison, A.J.; Pike, K.G.; Watson, S.P. Synlett, 2000, 1573.
=
Et
1 . BuLi , CHCl, , TIIF, -78°C
Et
2. HC1
*
& ,
Et - ; Rise, F. Synth. Conzniun., 2000, 30, 1767.
Netland, K.A.;
90% Et
OMe
MnO, , bentonite
92%
microwaves, 15 min
OH 0 Gciinez-I,ara, J.; GutiCrrez-PCrez, R.; Penieres-Canillo, G.; L6pez-CortCs,J.G.; Escudero-Salas, A.; Alvarez-'I'oledano, C . Synth. Cnniniun., 20U0, 30, 2713.
w
MLO
1. sec-BuLi ,THF , -78°C 2. CuI , DMF 3. l-MSCl 4.
5 . *rBAF,3 II,O, THF Bemen, J.-F.; Raymond, M.-N.; Moskowitz, €1.; Mavrareue. J, Tetruhedron LEtt., 1999, 40, 1313.
'
95% (G5:35 Z E )
Compendium of Organic Synthetic Methods, Vol 11
686
Section 374
1. Bu(2-Th)CuCNLiz , TIIF
B F3 -0Et-2
ATeBu
Ph
Ara~jo,M.A.; Bmientos-Astigarraga, R.E.; Ellensohn, R.M.; Terruheclron Lftt., 1999, 40, 5115.
Lee.;Park, J.; Lee, K.; Kim, H.-C. Tetruhedron Lett., 1999, 40, 7109. 10% Pd(0Ach
Ph W
P
h
P Y , MS 3 A , toiuene 0,,80"C, 2d
Nishimura, T.; Ohe, K.;
J . Am. Chem. SOC., 1999, 121, 2645.
0
fiost. B&;
60%
-%-I
* CP,, 10%CpRu(cod)Cl, DMF 15% cecb-7 frzo,600c 55% 10% EtCrCffI,CH,O€I Pinkerton, A.B. J. Am. Chem. Snc., 1999, 121, 4068. MqAlCl
*
D-?
0
93%
SiMq SiMe3 R.F.; Zaporowski, L.F.; Rogers, M. J. Org. Chem., 1999, 64, 9307.
PhCHO
acetone, microwaves
/J(
aq NaOH , 15 min * Ph Kad.;Kaur, K.P.; Singh, V.;Singh, J. Synth. Commun., 1999, 2Y, 2583.
80%
Section 374
Ketone - Alkene
msoh -
687
1. M q S i G C I I , GaC13
Ph
;-
2.H+
Ph+
75%
Tsukagoshi, T.; Arisawa, M. J. Am. Chein. SOC.,Z999, 121, 4074.
, .
+w
[Rh((RR)Me-DuPI 10s) )cod)] PF6 5 atin CO , DME ,55-60"C
GIt
6-20 h
0
.
99% (78%ee, SS)
; Itanii,
K.; Ito. Y. J. Am. Chem. SOC.,1999, 121, 4130, \
1.
I1 @Me 0
,hv , pentane
2. 200-240°C , BIIT ,PhII sealed ! d i e , 2-4 h \
Randall, M.L.; Lo, P.C.-K.; Bonitatehus Jr., P.J.; J. Ani. Cliern. SOC.,1999, 121, 4534.
Ho72
2. 1. COACO), NMO ,CIIzC12*MOh%',,
,,,d I 1 0
b0 rr
(
Mukai.; Kim, J.S.; Sonobe, 11.;
91x411
Me
:
,5 : 9 5 ) 88%
1111,,1~1~1
J. Org. Chein., 1999, 64, 6822.
Compendium of Organic Synthetic Methods, Vol 11
688
Section 374
q
2% A1 38 C 2 , buffer (PH 7.4) MeCN , 2 d
Org. k t t . , 1999,I , 59.
List, B.;
>95% (42% ee)
1. C02(CO), MS 4A , -10°C ,toluene * Br 2. TMANO
Br
90%
PCrez-Serrano, L.; Casarruhios, I..; Dominguez, G.; --Cast-
Synlett, 1999,587.
Ishizaki, M.; Iwahara, K.; Kyoumura, K.;
KTrn
0
Org. k t t . , 1999,1, 1187.
p 2 ( ~ ) ,
3.5 eq PhSMe , DCE 83"C, 10 min
;-
.
;
,
Yamada, M.;
@ /
'
; Nishizawa, M. Synlett, 1999,771.
4 eq4 CoF3 e q € I z, 0dioxane ,rt ,rt
/
OMe Tomatsu, A.; Takemura, S.; IIashimoto, K.;
-
@ / 0 Synlett, 1999, 1474.
87%
Section 376
Nitrile - Alkene
689
-
SECTION 375:
NITRILE NITRILE
/"
PBu3 ,300mPa, 50"C, 1 d
quant (77:23 trum:cis)
Jenner. G. Tetruhedron k t t . , 2000, 41, 3091.
-
SECTION 376:
NITRILE ALKENE
8-6
COzMe
COzMe
40%
Chavan.;Shrma, A.K.; Ethiraj, K.S. Synlett, 2001, 857.
=
Me
NEtz
MqSiCN ,DCM ,20"C
M q s i . c N NEtz
59%
15 h Me . N.V.; Kazantsev, A.V.; Borisenko, A.A.; Beletskaya, I.P. Tetruhedron, 2001, 57, 10309.
/x
"m,,,cat Bu4N HS04
50% aq NaOH, cyclohexane ether, 55"C, 5 5 h BA.; ,. Gierczak, A.H. Synthesis, 2001, 93. Ph
PhCI I 0
*
ba 71%
Ph
CIIz(CN),,NaZCO,,MS4A
*
,qCN
97% CN Siehenhaar. B.; Casagrande, B.; Studer, M.; Blaser, H.-U. Cun. J. Chem., 2001, 79,566. 70°C
PhCHO
CHZ(CNk ,TEBA , neat
Best., .. Narsaiah, A.V. J. Chem. Rex (S), 2001, 36.
* PhCH=C(CNk
88%
Section 376
Compendium of Organic Synthetic Methods, Vol 11
690
CH2(CN), , umtmpine PhCHO
P h T C N mimwaves , 2 min CN Wanp.; Wei, B.; Hu, Y.; Liu, Z.; Kang, L. J. Chern. Res. (S), 200Z, 146
j & /
20% CsOH*H@, NMP
Koradin, C.; Rodriguez, A.;
I
1. 3
CN
,LDA,THF
C6H13
-90°C 4 -60°C 2.2M aq HCI Tetruhedron Lett., 2000, 41, 6201.
cat CpzVC12 CN
MqSiCl, Zn DMF,rt,2h
-
Ph
Ph
NC
NII2
Zhou, L.; Ilirao. T. Tetruhedron Lett., 2000, 41, 8517. CH2(CN), , NH40Ac, 6 min
.-
hasic A1203,microwaves
Balalale.~.; Namati, N. Synth. Commun., 2000, 30, 869.
PhCHO
NC 43)
Y.;Nishizaki, Y.; Sugi.
Y, Chern. Lett., 2000, 998.
NH2 72%
phvm 80%
CN
CHz(CN), , PhH ,20"C, 6 h (HDTMA+-[Si]-MCM-41
Kuhuta.
Ph
; *hp
(57
PhCHO
80%
Synlett, 2000, 1452.
c1
PhI IC*cN
-+ pL rt
Ph
cp-7-C6Hl CP Kasatkin, A.N.;
87%
CN
Section 377
Alkene - Allcene
-
SECTION 377:
ALKENE ALKENE 0
w
avo.
CHZSHCN, Pd(0Ac)Z t-amyl alcohol ,8372
y OEt OEt
O
69 1
K2C03,2 h
Y.;Arisha, A.H.I. J. Org. Chem., 2001, 66, 4921. ]LLCO2Me
H” , PhH (degassed) sealed tube, 240°C
,,&”
’b,,
H
‘e,
1 S e q BHT
Tf3so
*9: 34%
,,\”’
mso
Deak, H.L.; Stokes, S.S.; w n e r . M .L,J. Am. Chem. SOC.,200Z, 123, 51.52.
T f 2 0 ,DCM , Z64utidine
(10
:
I) 65%
Harmata.;Bohnert, G . ;Barnes, C.L. Tetruhedron Lett., 2001, 42, 149. 7% [CpRu(NCMqhYPF6-
-)=41(””
acetone/THF , H20 , - 2 0 T , 4 h
Trost. B.M; Rudd, M.T. J. Am. Chem. SOC.,2001, 123, 8862.
77%
0
Meo27
MeOZC
P(c12, dioxane 7 0 T , 20 h
MCndez, M.; Mufioz, M.P.; Nevado, C.; Ckdenas, D.J.; J . Am. C h m .
SOC.,2001, 123, 10.511.
Compendium of Organic Synthetic Methods, Vol 11
692
Section 377
10% CpRu( MeCNbPF6 15%CeC13.7 H 2 0 1.5MVK, DMF 60°C, 6 h
Trost. B.M,; Pinkerton, A.B.; Seidel, M. J. Am. Chem. SOC.,2001, 123, 12466
DMF , Ru catalyst, rt
oq
86%
Trost. B.M.; Pinkerton, A.B.; Toste, F.D.; Sperrle, M. J. Am. Chem. SOC.2001, 123, 12504. 0
PhCI I 0
~
wSi
Ph
TMSCl 2. H30' ,-78°C Lee, B.S.; Gil, J.M.; Qh. D.Y. Tetruherfmn Leu.,2001, 42, 2345. 10% CpRu(MeCmPF6 MeO2C
0.2M acetone, It
M
78%
e
0
2
c
Meo2C
Trost.;Toste, F.D.; Shen, H . J. Am. Chem. SOC.,2000, 122, 2379.
87%
a
Alkene - Alkene
Section 377
693
BocHN
BocHN
NIIBoc
10%C ~ R U ( N C M C )PF6~+
0
Trost. B.M.; Surivet, J.-P. Angew. Chent. Int. Ed., 200Z,40, 1468.
SiMe.,
Tf20 ,-60°C
2,6-lutidine CH,Cl,
-
+
(88 12) Suzuki, H.; Monda, A.; Kuroda, C, Tetruhedron LRtt., 2001, 42, 1915.
b.
CP2
“‘3Y
2 eqEtCuCl , THF Et , 1 h ‘
Xi, C.; Kotora, M.; Nakajima, K.;
*
81%
bEr
J. Org. Chenz.,2000, 65, 945.
1. Me(ZnI)z, 2% Pdz(dba)JCHCIs &33% 10%P(3,5(CF3)2C,H,h
2.
66%
111111
*
&Br
Matsubara.; Ukai, K.; Toda, N.; Utimoto, K.; Oshima, K. Synlett, 2000, 995.
\
Compendium of Organic Synthetic Methods, Vol 11
694
mSMeFz CuCl ,DMF ,air
Ph
*
rt,3h
Nishihara, Y.;Ikegashira, K.; Toriyama, F.; Mori. A.: ITiyama, T. Bull. Chem. SOC.Jpn., 2000, 73, 985.
10% Ni(PPh3)4, toluene
/co2Et
-15,C
+
-10°C ,30min
Section 377
om
Ph
98%
*
71%
COZEt Saito. S.; Hirayama, K.; Kabuto, C.; Yamam oto. Y, J. Am. Chem. SOC., 2000,122, 10776.
TBDM mD SnBr3
0
* M e 3S i d G H 1 '
1.1, ether, r t , 1 h
Me3Si&
OSnBr3 2' B u 3 S n \ / l i L , ~ d l l DMF ,PdQZ(MeCN)2 60"C, 6h 3. Si02 ; Parrain, J.-L.; Aharbri, M. Lunot, S.A.; nibonnet, J.; Tetruhedron Irtt., 2000, 41, 8893.
C0,Me10% CpRu(MeCN)3BF6
64%
t
0.1 M acetone, rt, 4 h
Trost.;Toste, F.D. J. Am.
Chem. SOC., 1999, 121, 9728.
1. BuLi, -78°C 2. CQI13Br M+Si
3. heat
*L c61T13
82~70%
B t = henzotxiazyl Katritzky, A.R.; Serdyuk, L.; Toader, D.; Wang, X. J. Org. Chem., 1999, 64, 1888.
P hCI I 0 ~
R
.
dsiMe3 , BuLi , ZnCl, .r
Ni(cod), Ph F Zaporowski, . ; L.F.; Rogers, M. J. Org. Chern., 1999, 64, 9307.
58%
Section 378
695
Oxide - Akyne
cr: 4-
10% Rh(PPh3hOTf bluene , 110°C 0.01M
MeO2C
Wender.;Dyckman, A.J. Org. Lett., Z999, 1, 2089.
SECTION 378:
96%
C02Me
OXIDES - ALKYNES
*fl-
S02Ph
:l;:u;:
~
Ar = 3,541nethylphenyl Me rurstner.; . . Mathes, C. Org. Lett., 2001, 3, 221.
Ph
Ph PhCPCfI , MeOH, NEt, 20% PdCl2,20% CUI
Ph B uTe
rt,8h
0
u; de Andrade, L.11.;Silveira, C.C.; Moro, A.V.;
73%
a;
Tetrahedron Lett., 2001, 42, 8563.
0
1 . NaH 2. NaH ,(EtO)zP(OfH
THF , CCh
EtO-P,
* EtO/
II
o \
L
Ph
62% (>95% ZE) Kahalka. G.W,; Yang, K.; Wang, Z. Synth. Conintun., 2001, 31, 511.
Section 380
Compendium of Organic Synthetic Methods, Vol 11
696
0
1. C a r ,THF,<5"C
II
0
(EtohP-CFzZnBr Zhang, X.;
Bu-c+~
2
P(OEt),
2. B u G C - W , <s"C + fi
F
Tetruhedron k t t . , 2000, 41, 7791
51%
REVIEWS: "TheChemistry of Acetylenes and Allenic Sulfones,"
w.T.G. Tetruhcdron, 200Z, 57, 5263.
-
SECTION 379:
OXIDES ACID DERIVATIVES NO ADDITIONAL EXAMPLES
-
SECTION 380:
OXIDES ALCOHOLS, THIOLS
-Br
OEt
THF
*'.-kI '-0Et OEt
93%
A
Ranu.; Samanta, S.; Hajra, A. J. Org. Chin., 2001, 66, 7519. MgS04, MeOH, NaNOz 4.5 h
Ph
*
Ph
75%
NO,
Kalita, B.; B;lrua. N.C,.;Bezhilrua, M.; Bez, G . Synlett, 2001, 1411
EtNO, ,BnMe3NOH C
l
O
C
H
O
~
a
fl , 10 min
Bulhule, V.J.; Jnaneshwara, G.K.; Deshmukh, R.R.; Borate, H.B.; Synth. Connniun., 200Z, 3 , 3623.
e
\ /
E
91%
t
phoa Oxide - Alcohol
Section 380
;;:",1
~
p
A Do
Jh&ng&L;
h
697
b
O
H 47% (8020 trans:cis)
BEkvall, J.-E.; Leijonmarck, H. J. Chenz. SOC.,Perkin Trans. 1, 2001, 2051. MeN02,20% NEt, ,Cu(0Tfh
*HXo:
cat S-tBu-bisoxazoline ligand Co2Et Christensen, C.; h h l , K.; Chem. Conzniun., 2001, 2222.
>95% (92% ee)
1. PhSH , IIFIP
1
2.H202
84% (65:35 truns:cis) 0 HFIP = hexafhoroivopropanol Kesavan, V.; Bonnet-Delpon, D.; &$ye. J. -PATetruhedron Lett., 2000, 41, 2895.
Ph
dO~1
10%LiNI14, ,TIIF,60°C h *0 2 N EtNO,
Youn, W.; Kiln. Y .H. Synlert, 2000, 880.
4- O2NJOH
Me
(2.1
1)
:
0 98% (86:14 S,S:S,R) Nakamura, S.; Kuroyanagi, M.; Watanabe, Y . ;Toru, T. J. Chern. Snc., Perkin Truns. I , 2000, 3143.
BuCHO, KOM (powder) no wlvent
*
.. Balllnl.; Bosica, G.; Yarrini, M. Chem. Ixtt., 1999, 1105.
~
OH
B OH
91%
65% u
698
Kisanga, P.B.;
PhCI I 0
Compendium of Organic Synthetic Methods, Vol 11
Section 382
J . Org. Chem., 1999, 64, 4298.
EtNOz , Mg-AI hydrotdcite t
ph+N02 87% (3.25:1 threo:erythro)
Bulhule, V.J.; Deshpende, V.H.; Velu, S.; Sudalai. A; Sivasankar, S.; Sathe, V.T. Tetruhedron, 1999, SS, 9325. REVIEWS: "The Henry Keaction; Recent examples,"
SECTION 381
Tetruhedron , 2001, 57,915.
OXIDES - ALDEHYDES NO ADDITIONAL EXAMPLES
SECTION 382:
OXIDES - AMIDES
/\oms
(49 51) 95% Yoon, C.H.; Zaworotko, M.J.; Moulton, B.;Ju_nE. K.W, Org. LEfr., 2001, 3, 3539.
Oxide - Amine
Section 383
TMso
N ‘’
+
0-
NHPMP
PMP
+
E ‘t
699
‘L
2% c u catalyst, -100°C C02Et
C02Et
THF Et
94% (25:1 eryfhro:threo) 95% ee erythro Knudsen, K.R.; Risgaard, T.; Nishiwaki, N.; Gothelf, K.V.; Jmgensen, K.A. J. Am. Cherii. SOC.,2001, 123, 5843. 0
0
NsONHC02Et cao ,CH2CI2
!-OEt
*
‘OEt
rt,ld Fazio, A.;
EtOg!
40%
nTardella, ; P.A. Tetruhedron Lett., 2001, 42, 2185.
PhCIIO
&J.;
N /
s\ ,OMe
1. Cbz-NH2, MeOPClz
*
2. EtOH , NEt,
Z
O
CbzHN
E
+
t
Ph
\o\
A‘oH ph
CbzHN
47%
39%
Fun, N. J. Chem. SOC., Perkin Trans. 1, 2001, 1223. 0
II
/OMe
0
II ,
stage II B. bmsiunu
P-
OEt 43%
pH5.0,2O0C,7d
* &OH J. Org. Chem., 1999, 64, 6312. SECTION 383:
-
OXIDES AMINES
0
II
(s\N//\/o*s t- BU Tang, T.P.; Vollunan, S.K.; &an.
EtMgBr , TIIF
*f-BuH
P E
0
II
s,
N H
i\/ oms
.I.A. J. Org. Chem., 2001, 66, 8772.
91% (91:9 dr)
Compendium of Organic Synthetic Methods, Vol I1
700
Section 383
PhANl12
, €IOP(OEt)2
PhCHO
montmrillonite KSF microw aves , 3 min
fi'
b *l ~ . v J.S.; . Suhha Reddy, B.V.; Madan, Ch. Synlett, 2001, 1131.
P hNIIOII
* i-Pr
OEt
0
Me3Si0,
LPICHO , 5 M LiC104/ether (MeO)zPO(SiMe,>, It, 15 min
85%
.r
Ph
/ Ph
A/
97%
/ \
Me0
OMe
UA.; . . Zarei, M.; Alijanianzadeh, R.; Tavakol, H. Tetruhedron Lett., 2001, 42,3629. 0
EtO/
\OEt --
N
Et2NH , EtOH, refhx
E t O l
il,
Ph
42%
,to/'\
cat CuI , 3 0 min
NEt2 Tctruhedron Lett., 2001, 42, 4365.
Pananna, A.E.; Dugadina, A.V.; Zakharov, V.I.; N-TS
R
MeN&,5% Yb(0CPrh
*
i-PIOK ,TIIF, rt
E Ph
N
0
2 quant
Qian. C,; Gao, F.; Chen, R. TetruhecfronLett., 2001, 42, 4673. PhNH2, (EtOhP-OII 10% TaCls-Si02 ,DCE Ir
rt,22h
a
T
Chandrasekhar. S .; Prakash, S.J.; Jagadeshwar, V.; Narsihmulu, Ch. TetruherlronLJtt.,2001, 42, 5561.
l
92%
O
8
E
'OEt
0
PhCHO
II
PhNHz , A1203 , (EtOhP(0)H microwaves, 6 min
*
P h y \ \ O OEt Et NHPh Kaboudin.; Nazari, R. Tetruhcdron k t t . , 2001, 42, 8211.
87%
t
Section 383
Oxide - Amine
701
rt,lh
*
BnNHOH-HCl , EtOH , NEt3 93% (JNeil L&; Clator, E.; Southern, J.M.; Bickley, J.F.; Tapolczay, D.J. Tetruhedron Lert., 2001, 42, 8251. Ph
€IOP(OBt)2, ZXClA, McCN
*
It ,3.5 h
€I &\Bn
Bn
87%
0 YdddV.; . . Reddy, B.V.S.; Raj, K.S.; Reddy, B.; Prasad, A.R. Synthesis, 2001, 2277.
H.
CSHI,CI-IO
1.
/
OEt
0 k
.
1
o ~A1203, NH4OzCI-I *
microwaves, 3 min 2. P-TsOH, € 1 2 0 3. NaOII K a h n u d l n . B . h e m . Lett., 2001, 880.
,OEt
CsI4 1
66%
&\OEt 0
Et
92 9l%ee
Nishiwaki, N.;Knudsen, K.R.; Gothelf, K.V.; Angew. Chern. Int. Ed., 2001, 40, 2992. 1. NaH I
*
3. rncpha 4. t-BuOK, t-BuOH
:
8 erythro:threo 85% ee
xo2B I
N
85 X93%
Ph Burley, I.; Bilk, B.; Hewson. &T.; Newton, J.R..A. Tetruhedron Lett., 2000, 41, 8969.
702
Section 386
Compendium of Organic Synthetic Methods, Vol 11
OEt PhNH2, HOP(0Eth ,InC13
PhCHO
THF , ultrasound, 5 h Ph
Ranu. B.C,; Hajra, A.; Jana, U. Org. Lett., 1999, 1, 1141.
OXIDES - ESTERS
SECTION 384:
0
0
II
II
PhCHO , 0 . 2 S m ,TI-IF-HMPA
phYL?
rt,3h
p
h
~
'
8556 ~ ~
OBz m a k i . K; Itono, Y.; Nagafuji, A.; Naito, Y.; Shishido, T.; Takehira, K.; Makioka, Y.; Tankguchi, Y.; Fujiwara, H. J. Org. Chem. 2000, 65, 475. 0
A
1. F'(OMeb ,0°C -P 70°C 2. B z 2 0 , DBU , THF ,0°C
4
x
rt
ONp
P
3. chiral his-phosphine ,25"C /\ Rh(cod)OTf, 4 atm Hz O= MeOH, 2 d Burk. M.J.; Stammers, T.; Strauh, J.A. Org. Lett., 1999, I , 387.
c1
100%conversion 84% ee
SECTION 385: OXIDES - ETHERS, EPOXIDES, THIOETHERS 0
II
( K s \ P h
t-BuOK, t-BuOIi r t , 5 min
*
* q ' P h
Mukai.; Yamashita, €I.; Hanaoka, M. Org. Lett., 2001, 3, 3385.
SECTION 386:
OXIDES - HALIDES, SULFONATES
quant
t
Oxide - Ketone
Section 387
703
1 . 2 eq LDA
0
II
2. MqSiQ , THF , -78°C
E0-1 p
4
0
*
3. (PhS02)2NF, CzC16 El0 CzC14Brz1IZ 4. EtOLi , E O H , TIIF, 0°C Iorga, B.; Eyrnery, F.; Savignac, P. Synthesis, 2000, 576.
1J
PhS02Br, MeCN
NI
0
CMq
Wane.; Russell, G.A. J.
mzzfN
I
CM%
93% (115, cidtmns) Org. Chem., 1999, 64, 2346.
OXIDES - KETONES
SECTION 387: 0
II
-r\OEt
hv
89%
Ac20 ,TMSCl , Mg , DM*
x [ \ O E t
OEt
Kyoda, M.; Yokoyama, T.; Maekawa, H.; Ohno, T.;
'
ZnCrz07*3I-i,O
-p---c)Et
OEt Synlett, 2001, 1535. 0
0
1 I
*
neat, rt
-fi;yII
0 94% or. K; Sahhani, S.; Sardarian, A.-R. Tetrahedron Lett., 2001, 42, 4369.
OH
MeNOz, t-BuOK , toluene PhA
45%
P
h
chiral quaternary ammonium salt
Kim.;Huh, S.C. Tetruhedron, 2001, 57, 8933.
Ph 90%(35% ee)
Compendium of Organic Synthetic Methods, Vol 11
704
1
,OEt
BU
1
MZo3/a%
"OEt
,OEt [IOEt
Bu
micmwaves, 2minc
0
bhoudin.;
1. 02NEt , 4 eq ClPhNCO NEt3 ,TIIF
II
2. LDA, TIIF EtO 3. AcOH 4. TiC13 , aq HQ , DMP Lee, S.Y.; Lee, B.S.; Lee, C.-W.; Oh. D.Y, J. Org. Cham., 2000, 65, 256. EtOH/pEtO
Ph
ph*
75%
0
Nazari, R. Synth. Commun., 2001, 31, 2245.
0
Section 388
OSnBu3
NO2
,Bu4NBr, TIIF
c
45"C,4 h
88~64%
phw Ph
0
NO2
94% (0% without TBAB)
Yasuda, M.; Ohigashi, N.;-
Clwrtz. Lett., 2000, 1266.
jilGp
MeNOZ,Mg-Al-Ot-Bu
hydmtalcite catalyst * Ph Ph Choudarv., Kantam, M.L.; Kavita, B.; Reddy, Ch.V.; Figueras, F. Trtruherlron, 2000, 56,9357. Ph
a
MeNOz , KF/PN , 2 h
*
Ph
Ph
P N = "natural mineral phosphate"
I,ounv.;RCgnier, S. Tetruhedron Lett., SECTION 388:
A
/ococ6F5
93%
02 Ph
98%
1999, 40, 6221.
-
OXIDES NITRILES NHP(O)Ph2 20% heterohiinetallic complex
Ph
Yamada, K.i.; Moll, G.;
*
EtNOz ,CHZC12, -4O"C, 2 d
PhL
E f
fiOZ '
Synlett, 2001, 980.
t 77% (6:l unti:syn)
705
Oxide - Alkene
Section 389
P
EtzAICN , THF 6 5 T , 15 min
Et 80% (>98% de)
Fuano. J.L.G.; Garcia, M.C.; Laso, N.M.; Castro, A.M.M.; Jbrnos. Angew. Cheni. Int. Ed., 2001, 40, 2507.
-
OXIDES ALKENES
SECTION 389:
II
J.H.R
1.
c1 85%
Uuane. Y; Liang, C.-G.; Xu, Q.; He, Q.-W. J. Org. Chem., 2001, 66, 74. 0 II 'ITp-H
-
C-.II13
, toluene, ZYC, 1 h
Ph
3% Rh(I)(PPh3)3
-
+P quant
& IA,-B.;Zhao, C.-Q.;
c
J. Org. Chent., 2001, 66, 5929.
Ph
Ph
\
\
4
i'fi
0
Ph
3 eq € I 2 0 2
M e R ~ a 3 , o " C, 1 h 70% 14% 85% NazW02, rt , 1 h Choi, S.; Yang, .I.-D.; Ji, M.; Choi, H.; Kee, M.; Ahn, K.41.; Byeon, S.41.; Baik, W.; J. Org. Cheni., 2001, 66, 8192. PhSOzNa, NaI ,CAN m S 0 2 R * Ph MeCN ,rt , 4 5 mki Hair. V.; Augustine, A.; George, T.G.; Nair, L.G. Tetruhedron Lett., 2001, 42, 6763.
A \
Ph
76%
Compendium of Organic Synthetic Methods, Vol 11
706
Section 389
0
II
OMOM
2. EtMgBr 3. (EtO)zP(O)Cl
OTES William, A.D.;
-
'
Org. LEtt., 2001, 3, 2017.
100°C Mirzaei, F.; U . - B . :
76%
Tetruhedron Lett., 2001, 42, 297. MeNOz ,90°C
P hCHO
/
MCM41-NHz silica catalyst Demicheli, G . ; Maggi, R.; Mazzacani, A.; Righi, P.; Tetruehcrlron k t t . , 2002, 42, 2401.
'
NO2
ph
; Bigi,
98%
F.
SOzCHBr2
I
Liu, Y.; Wu, H.;
Synth. Comniun.,2001, 31, 47
IUY //S-ph SiMe,
B-SiMe3
1. Cp2Zr(H)a9THF. rt
2. PhSOCl ,THF, 40°C
. rd;E;IIuang, X. Synth.
COnlInUn.,
2001, 31, 615.
0
83%
707
Oxide - Alkene
Section 389
Zhao, C.-Q.;
P h =
-
; Goto,
M.;
Angew. Chem. Int. Ed., 2001, 40, 1929.
1. Cp&r(€I)Cl, THF , It 2. H,O
s\ Ph
*
Ph
P
78%
u S , P h
Ph@swp
Zhong, P.; 1Iuanp.; Ping-Guo, M. Tetrahedron, 2000, 56, 8921. PhO;,S
) Lee.; Me
1. 2 eq BuLi ,TIIF, 0°C 2. (EtO),POCI, THF, 0°C
3. PhCHO
=
84%
Me Lee, C.-W.; Jung, J.H.; Bh. D.Y. Synth. Commun., 2000, 30, 279. MeN02,25”CI 10 min gel entrap+
base catdEt
m; Uppalla, L.S. Synth. Conzmun., 2000, 30, 2071. I
.
GH13
-
Han, L.-B.;
GH13
(PhOhP(O)SPh, toluene, 5 h 3% Pd(PPh3)4, 100°C
Chcm. Lctt., 1999, 863.
*
)=-.
PhS
/OPh
h O ‘ [
0
92%
REVIEWS: “a-Phosphonovinyl Carbanions in Organic Synthesis,” Jvlinami. T,; Okauchi, T.; Kouno, R. Synthesis, 2001, 349.
Compendium of Organic Synthetic Methods, Vol 11
708
SECTION 390:
Section 389
OXIDES - OXIDES
Allen Jr., A,; Manke, D.R.; J .in W. TefruhedronLeft., 2000, 41, 15 1.
+NO2 Ph
1. chirat TADDOL phosphite ,Et,Zn
TMEDA ,'ITIF, -78°C
2. TMSCl ,MeCN , reflux 3. DCM , H,O , rt
*
H HO'
o
89~87% (92%e e ) Cndtrb.; Tedeschi, L.; Bats, J.W. Angcw. Chem. Int. Ed., 2000, 39, 4605. 4
1
.
v Ph
O
Comvendium of Orpanic Svnthetic Method8 “
V
Michael B. Srnitk Copyright 0 2003 by John Wiley & Sons, Inc
AUTHOR INDEX
Aharhri, M. Ahazi, S. Ahhas, S. Ahhasi, M. Ahhoud, K.A. Ahdi, S.H.R.
U
bhe. M. Ahe, S. Ahe, T. Ahe, Y. Ahella, C.A.M. Ahernathy, C.D. Ahraham, L. Abraham, S. Ahrunhosa, I.
Aceiia, J.L. Ackermann, L. Acton, A. W. Adamo, M.F.A. Adams, N.D. Adihi, €I. Adiey, K. ,4clolfsson. H. Adrian Jr.. J.C. Adrio, J. Adude, R.N. k i l t s , S.L. Aelterman, W. Afanas'ev, V.V. Afunas'eva, L. Afonso. C . G M , Afonso, M.M. Ag ami,C . Agata, I.
Aghapoor, K. Aghapour, G . Aghiniz, A. Agrios, K.A.
190, 499, 694 436 257 382 476 129 350, 351 271, 346, 364, 49 1 343 374, 518 608 621 402 064 670 206, 270, 605 127 359 527 429, 456, 467 572 051, 343, 351, 353, 356, 391, 545 361 028 051, 416 099, 106 139 360, 582, 500 599, 602 46 1 472 460 382, 603 429 319, 329 077, 132, 533 660 452 152 025, 053 211, 218, 234, 238, 240, 341, 361, 394, 654 096 367,555 127 256
Aguirre, S.
AhhIxL
ahman, J. Ahmed, A. Ahmed, G. Ahmed, M. Ahmed, Md.M. Ahmed, S. Ahn, C. Ahn, 11.
A h , Y. Ahrendt, K.A. Aihara, H. Aikawa, K. Ainge, S.W. Ajami, D. Ajamian, A. Akai, S. m a n c h i . K.G. Akanintsu, K. Akashi, M. Akbar, A. Akhmedov, i.M. Akhrem, A.A. fihreni. I. Akiba, D. Ntila, S. Ntins, B.G. ,4kita. H. Akita, K. Akiyma, R.
Ntula, M.R. Aladro, F.J. Alamdmi, R.F. ,41hanese. D. AlhCniz, A.C. ALbert, K. Albert, S . A1binj.J,4lcaide. B.
709
183 553 153 591 363 245, 267,460 045 170, 171 571 067 186, 195, 219, 350, 705 260, 268 180 395 429 034 638 088, 096, 097, 099, loo, 101, 112 427 389 510 106, 368,423 670 174 092 597 669 319,329 340 586 480 653 130 277, 500 040, 235, 278, 286, 569, 607, 608, 611 270 495 077,083 151, 253 455 091 643 375 033, 234, 307, 567,579
710
AUTIIOR INDEX
552 450 126, 195, 196, 205, 208, 557 Alexander, C.W. 579 Alfiiro, R. 482 ali Zolfigol, M. 094 498 Ali, I.. Ali, I.S. 473 093, 289, 390 ALImL Ali, M.M. 560 Ali, S.I. 259 Aliakhar, A. 092 Alijanianzadeh, R. 700 Aliyan, H. 107, 315, 415, 526 Allaire, F.S. 343 Allamand, J. 195 Allegretti, M. 137 Allen Jr., A. 708 Allen, D. 160, 378 Allen, J.V. 354 Allen, N.T. 069 Allenmark, S. 215 Allevi. P, 569 Allison, J.C. 254 Allwein, S.P. 455 Almeer, S. 479 Almendros, P. 307,567, 579 Alonso, D.A. 067 Alonso, E. 238, 341, 654 Alonso, F. 151, 236 Alonso, I. 175 Alonso, J.M. 307 253, 298, 325, &=-H. 564, 566, 600, 631, 636, 639 Alper, P.B. 286 Alptiirk, 0. 597 Alsters, P. 091 Altundas, R. 415 105 Allundns. .R: Alvarez, P. 090 Alvarez, R. I84 Alvarez-Builla, J. 449 Alvarez-Garcia, A. 40 1 Alvmz-Manzaneda, E.J. 094, 193, 333, 381, 387, 541 Alvarez-Toledano, C. 685 Aly, M.F. 307 Amantini, D. 074, 532 Ales, A.
Amaresh, R.R. Amedjkouh, M. Amemiya, T. h e y , A. h i i . H. Amini, M.K. Amrein, S.
AmLli. Anada, K.
Anand, N.K. Anand, R.V. Anastasia, L. Anatasia, M. Anathouju, S.R. Anderson, A.M. son. J.C, Anderson. S& Anderson, W.K. Andenson. P.G, Andes, C. Ando, J.-i.
AIldQ& AldLIL
AuLL
h d r a d e . C.K.Z, Andre d'Avignon, D. Andreae, M.R.M. Andrks, J.M. Andresen, B.M. Andreu, M.G. Andrews, A.T. Andrews, I.P.
-
Anilkumar, G. Anilkumar, R. Anjancyulu, S.
Anjum, A. Anlauf, U. Anoro, S. Anselmi, C. Anthony, L. Antilla, J.C. bntonioletti. R, Antoniotti, S. Antunes, A.M.M.
168 553 676 067 164, 271 080 178 619 130 426,485 113, 359 002 569 561 373 100 589 334 417 067,558 455 185, 484 442 183, 210, 457, 528,562 097 035 641 330, 356 395, 515 159, 304 142 060, 134 141, 147 178358 360 394,525, 529 355, 644 261 045, 047,301, 303 010 228 262 138 442 272, 276 445, 528, 533 399 569
AUTHOR INDEX
Anwar, U. Anzai, M. Anzai, S. Aoki, M. Aoki, T. Aoki, Y. Aouad, E. Aoyagi, T. Apaydun, S. Aponick, A. Appelhe, R. Appella, D.H. Appelt, H.R. Aprile, C. Aquino, L.B. Arahindoo, B. Aragoncillo, C. Arai, H. Arai, M.A. Arai, N. k a i * s. Arai, T. ,4raki. S. Araki, T. Araki, Y. Arason, K.M. Araujo, M.A.
Arcudi..
Arcari, J.T. Ardakani, A. Arduenlro m. A .I. Arefolov, A. Arerno, N. Arena. C.G. Arend, M. Arends, I.W.C.E. Arifuddin, M. Arikan, N. Arimura, K. Arisawa, M. Arisha, A.II.1.
&luJ. AxmuLL
558, 658 035 006 011, 393, 474 027 268 622 320 242, 685 597 266 300, 583 458 159, 201 030 547 526 402 097 567 542 524 416 433, 647 524 032, 506 332 078 326 686 137, 165, 208, 616, 640, 655 66 1 349 489 664 525 128,199 279, 607 330, 355, 356, 357, 361, 362, 390, 392 099, 106, 301 418 332 261, 586, 634, 667, 670, 687 69 1 083, 263 237,527
ArmstroneB, Amauld, T. Arnold, L A . h a n z , J. h a t e , M.
Arredondo, V.M. Arroyo, N. ,kterhurn. J& Artrnann III, G.D. Arm, M. Aruna, S. Arvidsson, P.I. Asadullah, M. Asai, M. Asakawa, K. Asano, T. Asano, Y. Asao, N. Asaumi, T. Asghari, J. Asghui, S. Ashford. S.W. Ashtiani, A.M. Askokan, C.V. Aso, N. Astashko, D.A. Ates, A. Atherton, J.C.C. Atherton, M.J. Atienza, C. Atkin, M.A. Atmani, A. Attolini, M. Au, S.-M.
AdLL
Aubert, D.
AuL!a
Augustine, A.
Augustyns, B. c o e c u Aulrekoetxea, N. Awry. M.A. Avila-16rraca. J.G, Axelsson, 0.
Ax.mmdL Ayers, J.T.
711
351, 360, 363, 570, 645 408,460 196, 199, 452 593 487 284 028 113,192 246 228 447 030 014 518 029,537, 539 057,060 468 181 428, 436, 438 274,331 048, 107, 372 439 014 114 334 368 549 646 086, 112 059 374 164 570 666 055 255 238, 256.257 339 042, 209, 463 376, 646, 662, 705 086 487, 650, 653 487 076, 297 312 142 248 334
AUTHOR INDEX
712
Avers. T.A. Ayuha, S . Azadhar, M.R. Azann, M.
Azevedo, N.R. Azizi, N. Aznar, F. &em. ti,
Baati, P. Baati, R.
A -.
Baba, A.R. Baha, K. Baha, Y. Bahu, K.G. Bahu, R.S. Bahu, S.A. $ach. T. Bachnann, S. Back, D.Y. Back, € I S . .rk. . .G. Bncknejad, €1. 7
Badarinuayana, V Badine, D.M. Bae, J.W. Bae, W. Baek, H. Baeschlin, D.K. Bagherzadeh, M. Bagnell, L. Bagnoli, L. Bahraini, K.
523 370, 662 093, 191, 411, 476 105 035 266, 596 678 100, 272, 379
108 034,037, 081 032, 066, 090, 156, 192, 267, 292, 377, 381, 384, 388, 409, 504, 547, 607, 682, 704 305 101 429 077 074, 112 109, 406 343,575 09 1 621 400 619, 696 095 130, 175, 453, 461, 500, 503, 509, 519, 664, 697 254 552 277, 296, 305, 599 063 668 621 413, 477 613 020 622 356
Bahwa. J.S. Bahzad, D.
€!An
Bai, K.H. Bai, L. Bai, Y. Baik, T.-G. Baik, W. BailCn, M.A. F. Baillie, C. Bajji, A.C. Bajpai, A.R. Bak, R.R. Bakale, R.P. Baker. D.C. Bakhtiilli, K. Bakke, J.M.
JbkCiL EhkQSJ
Bakthadoss, M. Bdagopal, L. Balakrishna, M.S. Bdakumar, R. Balamuragan, R. Balan, D. Balasubramanian, B .N. Balasuhramanian, S. Balhi, M. Balduzzi, S. Balenkova, E.S. Ball, Z.T. . . Ballm. R,
Bahne. G. Bnlork, I.M.
Balsells, J . Baltork, I.M. Bandarage, U.K. Bandcar. B.P,
083 373 504,506 277 492 166, 252 221, 224, 225, 536, 661 261, 277, 705 227,229 081, 281 140 172 418 308 472 629 594 423 294 517 194 104 458 376 477 018,383 257, 690 652 582 017 095, 586 619 044, 646 303 088 541 475, 665 010, 473,476 427 110, 170, 416, 481, 609, 671, 697 618, 650, 656 099 218 106 389 019, 043, 075, 078, 095, 111,
AUTHOR INDEX
Bandini, E. Bandini, M. Bandyopadhyay, A. Bandyopadhyay, T. Baneres, J.-L. Banerji, A. Banfield, S.C. Bang, K. Banik. B.K.
Banik, I. Bansal, G. Banwell. M, Bao, M. Bao, W. Bar, G. Barakat, K.J. Baran, P.S. Barathi, B. Baratta, S. Barha. F. Barha, G.R. Barbas 111, C.F. Barheris, M. Barhoni, L. Barbosa, F. Barhro, A. Barbrv. D. Barchin, B.M. Barcinia, J.O. Bardales, E. Bkfacker, L. Bargiggia, F. Bargon, R.M. Barhate, N.B. Brufidadi, R. Bark, D.Y. Bark, T. Barker, D. Barker, S.F. Barkin, J.L.
112, 143, 312, 322, 367, 389, 424, 471, 707 248 024, 033, 647 584, 614 383 260 308 45 0 560 038,554 067, 095, 110, 161, 277, 283, 296, 305, 306, 390, 472, 507, 576 283,306 138 447 228 447 038 654 161 683 346 135 602 68 1 022, 182, 203, 540, 604, 688 212 170, 416 513 204 278 449 145 446 20 8 634 3.56 314, 374 399 516 318 625 307 160 599,602
Barks, J.M. Barina, D.K. Bannan, D.C. Barnes, C.L. Barnes, D.M. Barnhurst, L.A. Baroni, A.C.M. Barragan, V. Barrero. A.F,
Bcurett, I.C. parriau1t. L. B airientosAstigarraga, R.E. Barros, D. Barros, M.T. Barthuber, A. Bartbk, M. Bai-toli. G.
Bartolozzi, A. Barton, D.H.R. Bartosch, M. Baiua, A. Barua. N.C, Barua, P.M.B. Baiuah, A. Baruah, B. Baruah. M. Barun, 0. Barzana, E. Barzilay, C.M. B a s k , A. Basavaiah. D. Baskaran. S. Bass, J.
713
083 119, 218, 561, 672, 678 034, 081, 108, 558 423, 441 69 1 210 098, 341 653, 663 263 094, 193, 333, 381, 387, 502, 541 030, 095, 212, 443, 460, 479 302 46 1 686 349,354 075 259 541 384 068, 184, 210, 368, 370, 503, 504, 506, 548, 604, 681 246 408 513 263 114, 263, 471, 696 665 47 1 448 020, 029, 384, 606 564 472 453 3 13 161, 180, 458, 531, 631 249 519 090 332
AUTHOR INDEX
714
Bastin, S. Basu, M.K. Batmen, B. Bates, C.G. Bates. R.W, pjjtev. R.4, ~ a t r ; lri. , Bats, J.W. Battaglia, L. Battle, G.M. Baucherel, X. Baudoux, J. Bauhy, M. Bauduin, C. Bauer, A. Baumstuk, A.L. Baxter, C.A.
BWLE.
Baylon, C. Bazh-Tejeda, B.
J&aLJ?. Beare, N.A. Beauchamp, P.S. Beaucheinin, A. Behhington, D. Beck, B. Beck, E.J. Beck, K. Beck, V.H. ec e
Becker, II. Decker. I.F. Beckniann, A. Beckmann, 0. Bedford. R.B.
B ~ ~ u J.-P. C,
Begum, F. Begum, S . Dehar. V. Behhahani, F.K. Behhahani, I.K. Beheshtiha, Y.S.
025 067, 110, 305 602 276 577 037, 041, 132, 222, 558, 572 429 170, 708 108 235 104 372 187 473 181 393 638 275 047, 651 632 266 233, 246, 516, 590 321 183 213, 219 192 568 445 456 086 110, 277, 283, 296, 305, 306, 390, 472, 507, 576 490 095 008
330 258, 371, 374, 580, 608 141 358, 517, 624, 697 311 311 074 345 526 079, 505
Bei, X. Belderrain,T.R. Belelie, J.L.
lkdLIsL
Bellassoue~
Lklkla
Bellesia, F. Bellettini, J.R. Bellucci, M.C. Belluti, F. Belokon'. Y.N. Belotti, D. Ben-Daniel, R. Ben-David, I. Ben-David, Y. Benach, E. Benacorse, H.G. BCnxd, A. Denati. J.. Bendale, P.M. Benet-B uchholz, J. Benhaim, C. Benhida. L Beni, Y.A. Bennahi, S. Bennett, D.M. Bensari, A. Benson, G.A. Bentley, J. Bentley, P.A. Bercuw, J.W. Berente, 2. Berger, D. m a n .
R.G.
Bergmann, D.J. Bergstad, K. BCrillon, L.
293 212 222 293,429, 689 163 498 104, 142, 187, 23 1, 254, 264, 271, 298, 327, 390, 421, 466, 496, 501, 615, 496 561,585 019 138, 323,636 210, 368, 506, 681 339 599, GOO, 648, 649 403 091 624 478 412 297 669 572 257,413 019 635 126, 195,08 148 10s 312, 356 207 397, 604 591 503 511 192 350,352 274 208 588 180, 272 287, 363 183, 270, 326 509 347
AUTHOR INDEX
Berkessel. Berlin, 0. Bernacka, E. Bernad, P.L. Bernardi, C.R. Bernardinelli, G. Bernasconi, S. Berrien, J.-F. Bertand, S. Berthelette, C. Berthiaume, D. Bertilsson, S.K. Bertoniere, N.R. Bertozzi, F. Bertus. P.
Besbore. D.C. Beslin, P. Bessnrtl. Y. Bessieres, B. Bessmertnykh, A.G. Besson. T, Bestetti, G. Betancort, J.M. Bethell, D. Betzemeier, B. Bez, G. Bezharua, M. Bezharua, M.S. Bhaduri, A.P. Bhalerao, U.T. Bhlunare, N.K. Bhanumathi, N.
Bhar. S .
Bharathi. P. Bhat, L. Bhatiu, K.A. Bhatt, A. Bhattachwyya, A. Qhawal. B.M, Bhongle, N.N. Bhosale, D.G. Biagetti, M. Bickley, J.F. Bieher. L.W. B i d , C.
330, 356 47 8 230 446, 666 578 205 353 685 600 441 630 558 269 463 005, 035, 216, 217, 278, 298, 380, 493, 494, 588 24 1 471 328 533 293 314 353 182, 203 349,354 095, 147, 362 114, 263, 696 696 114 287 084,088 417 084,516, 566 627 124, 284, 405, 564 45 8 100 050, 403 357, 366 646 267, 297 228 629 020 636 350, 352, 701 305, 363 055
Biehl, E.R. Bielawski, C.W. Bieniek, M. Biermann, U. Bigdeli, M.A. Bigi, F. Bilic, B. Qillard. T. Billet, M. Birikaki, L. Biscoe, M.R. Bisi, A. Bittner. S. Black, P.J. Black, S.J. Blackburn, L. Blacker, A.J. Blacker, J. Blacklock, T. Blacklock, T.J. Blackwell, J.M. Blake, A.J. Blanco, O.M. Blanco-Urgeiti, J. Blankenstein, J. Blankinship, M.J. Blann, K. Blaser, H.-U.
EibsLE
Blay, G. Blazek, J.M. 3lechert. S, Blomgren, P.A. Blond, G. Bluet, G. Bluhm, H. Bluin. .I. Bohhitt. J.M. Bodas, M.S. Bode, J.W. Bochnann, K. Boebel, T.A. Boesten, W.H.J. Boezio, A.A.
BwlaLn
Bdgevig, A.
715
168 456 458 188 412 615, 635, 706 701 643 611 548 273 339 327 176 479 440, 611 130 054, 234 083, 308 010, 308, 373 086, 240 333 163 467 674, 680 158 4 10 323 061, 689 243 075 412 100 436, 456, 457, 463, 675 006, 146, 147, 148 643 65 1 550, 632 526 478 096 3 14 021,535 441 216 565 3 14 010 580
716
Bohm, V.P.W. Bohnert, G. Boivin, R.P. Bolesov, I.G. D o h . C. Bolourtchian, M. Bomnierijn, S. Bofiaga, L.V.R. Bonditatehus Jr., P.J. Bondock, S. Bonesi, S . M . Bonilla, R.J. Bonini, B.F. Bonini, C. Bonitatebus Jr., P.J. Bonitatehus, P.J. Bonioch. .I. Bonnert, K.V. Bonnet, V. Bonnet-Delpon, D. Booth, R.S. Borah, R. Boral, S. Borate, 1I.B. Borg, G . Borginann, C. Borisenko, A.A. Borowski, S. Boiwdon, E. Bortolini, 0. Bomah, A. Boruah, M. Boruah. K.C. Bosch. E. Bosch, I. Bosch, .I. Bosco, M.
Dose. D.S, Bose, G . Bosica, G
AUTHOR INDEX
003, 141 69 1 630 516 021, 026, 061, 091, 095, 096, 330 089, 093, 097, 102,593 178 680 460 340 372 160 556 512 687 465 242 394 139 358, 517, 624, 697 134 267 61 1 696 020 244, 496 104 689 158 43 1 369 351 262, 338, 448 299 170 386 302 307, 604 068, 210, 368, 503, 504, 506, 548, 604 161 106, 107, 308, 405, 419, 420, 689 108, 109, 665 110, 170, 481,
Bossart, M. Boston, T.S. Bothe, U. Boto, A.
€mkbL
Bottcher, A. Bottex, M. Boucard, V. Bouchu, D. Boukrat, L. Boukhris, S. Boulaajaj, S. Bourdon, J. Bourguet, E. Bourguir, F. Bouquet, C.
Bower, J. Boyall, D.
E!QmA Braea. A.L. Braihante, 1I.T.S. 1 ante. M.E.F, Braier, A. Branchaud. B.P, Branco, L.C. Brandi, A. Brands, K.M. Briise. S. Bratovanov, S.S.
rirma!L
Braun, R.U. Brauner, .I. Breindl, C.
&LFL
lhslLK’
Brkmond, N. Brenek, S.J. Brenner, E.
609, 671, 697 081 307 237 560 617 490 650 429 207 337 573 674 358 2(io 055 349,354 026, 563 3 15 445, 528, 533, 666 613 421 486 081 030, 095, 212, 460,479, 552 030, 310, 494, 578, 632, 647, 695 664 664 008 446 077 569 697 262, 414 154 311, 552 203 407 668 045,046 271, 298 105, 175 495 181 072, 159, 304 290
717
AUTHOR INDEX
Breno, K.L. Breuil-Desvergnes, V. Breuzard, J. Bricout, I I . Bridge, A. Bridge, C.F. Brielles, C. Bfigud. T, Brillon, D. Brinlunann, A. Brinksma, .I. Bmcud, .I. Brochu, C. Brogan, J.B. Broggini, G. Brook. M.AL Brookes, P. Brooks, C.A. Brooks, C.D. Browder, C.C. Brown, C.D. Brown, D.S. Brown, E. Brown, G.A. Brown, R.A. Brown, R.E. Brown, S.M. Brown, W. Browning, R.C. Broxterinan. Bruah. K.C. Brucud, J.
0.a
Brun, E.M. Bruneau, C. Bruneau, S. Brunel. J.M. Brunette, S.R. Brunner, M. Brunton, S.A. Brusse, J. Bryans, J.S. Brvson. T.A. Biqszcz, M. Buhert, C.
44 1 614 184 082 235 42 1 274 532 482 287, 307 284 359 053 181 662 306 088, 233 42 1 155, 295, 441 192 015 178 174 092, 685 669 069 053,071, 319 191 386 054, 097 26 1 254 276, 565 171 025 488 663 009, 229, 499 612, 634 429 058, 196, 199, 531, 533 169 490 245 323 243 020, 310 01 1 054
Buhnov. Y.N, Buhnov. Yu.N. Bucher, B.
Buck, M. Buckley, B. Bui, T. Bulhule, V.J. Bull, S.D. Bulliard, M.
J3uddxL
Bunlaksananusurn, T. Buono. G. Buonora, P. Bur, S.K. Burkart, M. Burkhal-dt, S. Burley, I. Burns, S.E. B.uton. D.J. Burton, K. Buschmann, N. Bustamante, J.M. Busujima, T. Butova, E.D. Bydlinski, G.A.S. By-11, S.-H. Bvers. J.N. Byme, J.J. Bytschkov, I.
Caheza, I.
269, 283 270 521 228 002,143, 149, 153, 159, 176, 177, 201, 245, 254, 272, 276, 280, 282, 285, 289, 290, 291, 294, 296, 327, 336, 347, 407, 437 012 349 022, 604 454 696, 698 241, 279, 281 323 389 254,449 078 422 058, 196, 199, 531,533 620 211 058, 702 328 06 1 701 449 528, 664, 696 214 457, 463 149 495 545,546 374 212 705 148 280, 609 264, 387
028 067
718
AUTHOR INDEX
Cahianca, E. Cabrera, G. CabEri, s.
. .
Caddick. S. Cadot, c.
Cai, D. Cai, K. Cai, W. Cai, X. Caillot, I;. Caizzo, A. Calahrese, J.C. Calahrb, G.P. Caldenjn, 0. Caldwell, J.J. Callaghan, 0. Calmes. M. CalB. v. M.& Calvo, R.L. Camacho, D.H. C~IIIIXI~E J.-M, W. Campagna, S. -,e. J.-U Camphell, E. Camphell, E.J. Camphell, J.E. Campi, E.M. Campo, M.A. Cumnos. K.R,
Camnos. P.J, Canet, J.-L. Caiiihano, V. Cao, B.
Cao, G.-A. Cao, P.
CW. y.-o. Capan, E. Capozzi, M.A.M. Capraro, D.
652 652 024 165, 208, 233, 466, 616, 640 003, 257 070 372 182, 347, 401, 449 425 405 390 072. 275 220; 221 137 211 457 489 199 499 316 568 062 185, 206, 217, 45 8 539 658 650 550 004,005, 665 632 685 045 148 287, 363 40 1 425 168, 276, 593 605, 606 37 1 594 490 333, 431, 432, 46 1 338, 421 547 48 1 036 662
Caputo, T.D. Caracoti, A. Carhallares, S.
Carhoni. B,
Cudellicchio, C. Cardenas, G.I. Cirdenas, D.J.
-10.
G,
Cardona, F. Cardoso, A.L. Curloni, S. Carrnichael, A.J. Carnell. A.J. Caro, M.
i2imllA
call.,G.
J.-F.
Cmura, F. Ira. E.EI,
Carreiio, M.C. Carretero. X.C, C m u a u x . F. Cani6, D. Carrigan, M.D. Carrillo, J.R. Carroll, T.M. Carter, C.A.G. Carter, D.S. Cartwright, C. Casagrande, B . Casanuhios, L.
Cascia, L. Casolari, S. Cassol, T.M. Castanet. Y, Castafio, A.M. Castedo. L,
Castellanos, L.R. Castello, c. Castillo-Colaux, c. Castrefio, P. Castro, A.M.M. Castro, I. Catalano, V.J.
554 549 450 032 481,482 268 691 241, 596 474 301 635 374 466 361 168 422 322, 323,400 331 341 021, 286, 426, 486, 488, 535, 485 371 024,175, 223, 46 1 032 215 078, 108, 110 165 017 412 448, 657 594 689 674, 676, 680, 688 165 547 067 123 400 452,460 226, 467 148 121,534 501 204 705 068 163
AUTHOR INDEX
Catanese, A.
636 135, 146 Catteau, J.-P. 479 Cavarischia, C. 336 Cavazzini, M. 095, 128 Caveda-Cepas, s. 649 Cavero, M. 602 Cavicchiioli, M. 163, 650 Cecchetto, A. 092 Cefalo, D.R. 454, 460 Cerezo, A.d.F. 145 Cerichelli, G. 655 Certal, v. 623 Ceschi, M.A. 112 043, 044, 068, 397, 679 Cha. J.S. 064, 090 Cha, J.W. 554 Chahoche, C. 449 Chaghamarani, A.G. 473 Chahhoun. R. 094, 193, 333, 381, 387, 541 Chaikovskii, V.K. 372 Chakrahartv. 248 aakrahorti. A.K 013, 077, 086, 313, 418 Chakrahorty, V. 020 Chamberlin, R.M. 192 374 Chamkers-Asman, D.M 236 Chan. A.S.C. 022, 023, 024, 025, 053, 056, 062, 157, 158, 196, 198, 201, 258, 423, 485, 530, 542 Chan, H-L. 328 Chan, J. 556 Chan. K.S. 026, 292 Chan, M.C.W. 404 Chan, P.-M. 668 Chan, P.W.H. 393 Chnn. TJI. 024, 038, 039, 040, 240, 507, 556,582 W.L 485 Chand, P.K. 107 . . . 25 8 Chandra, K.L. 076, 111, 140, 457
Chandraiah, L. Chandrasekhar, M.
Chandrashekar, V. Chandupatla, K.R. Chang, B.-R. Chang, D. Chang, G. Chang, H.-M. Chang, I.-H. Chang, J.-W. Chang, M.-Y.
Chang, V. Chang, W.-S. Chann, K. Chao, B. Chao, L.C.F. Chao, S.-D. Chaplin, J.H. Chapman, C.J. Char, A.S.C. Charette. A.B, Charonnet, E. Chmada, B. Chmuault, L. Chary, K.P. Chase, E. Chataigner, I.
Chatterjee, A.K. Chatterton, C. Chatti, S.
719
262, 287, 344 123,509 279 077, 082, 106, 245, 260, 261, 262, 267, 285, 287,300, 319, 344, 399, 563, 588, 700 53 1 180 253 050,051 367 186,555 314 136,596 253 253 006, 038, 094, 203, 423, 447, 492, 554 220,221 205 525 585 491 038, 314 654 402 128 181, 212, 213, 216, 219, 314, 441 677 517 139, 453 073, 101, 301, 305,530 303 041 249, 274, 331, 379, 404, 425, 435,581, 672 175, 461, 465, 632 131 393 520 054, 450 016
AIJIIIOR INDEX
720
Chaudhari, S.S. Chaudhary, K. Chaudhaiy, S. Chaudhuri, M.K. Chaudhuri, S.K. Chauhan, K.K. Chauhan, S. chaumeil. I-L Chavan. S.P, Chavant, P.-Y Chavarot, M. Che. C.-M.
,-
eL*
ChellC-Regnaut, I.
mau.L
Chen, B. Chen, B . 4 . Chen, B.-h. Chen. C.-T. Chen, D.4. Chen, D.-W.
LkaLJL
e" Chen, G. Chen, H . 4 -
Chen. J Chen, 1.-X.
Chen, M.-F. Chen, P. Chen, R. Chen, S.-F. Chen, w . Chen, Chen, Chen, Chen, Chen.
X. X.-M. Y. Y.-C. Y.-J.
106, 368, 423 513 399 665 627 087 287 063, 447 144 323, 415, 625, 689 280, 609 280, 609 255, 349, 404, 668 012 097 012,231 015, 088 408 42 1 31 1 147, 189, 220, 221, 657 038, 314, 318 41 1 039 107 106, 418 128, 330 053, 145, 213, 214, 217, 388 176, 193, 348, 45 1 412 416 009, 163, 489, 633 414 54 1 333, 334, 351, 700 229 131, 140, 410, 561 592 025 497 053 204, 476
Chen, Z. Z.-C. Chen,Y. m e . C.-H. Cheng, D. Cheng, D.-P. Cheng, 11.-S. Cheng, J. Cheng, K.-F. Cheng, K.-m. Cheng, K.-W. Cheng, T. Cheng, W.-C. Cheng, X. Cheng, Y. &on? CLS. Cheong, J.H. Cheong, J.W. Cherkdoui, €1. CherouVrier, F. ChCry, F. Cheshire, D.K. Chetri, A.B. Cheung, K.-K. Chevallier, F. Chhibher, M. Chi, D.Y. Chi, H. Chi, Z . Chiacchio, U. Chiang, J.P. Chiarini, M. Chiarini, M.
!2lhJL
Chiha, N. Chiha, T. Chick, J.E. Chieffi, A. Chinchilla, R. Chino, M. Chirsman, W. Chirstmann, M.
c2liuL
Chiusoli, G.P. Cho. B.TT.
311 167, 224, 225, 337, 411, 482, 185,394 226 117, 186, 555, 576 179,216 411 341 275 534 657 404 294 668 602 418 03 1 444 261 390 035 652
652
011 375 534
095
353, 358, 380, 670 419 042 415 360 662 208 655 124, 220, 317, 338,339 538 468 602 153, 407 227, 229 496 542 033 534 310 026, 027, 029,
AUIIIIOR INDEX
m. C.-G.
Cho, C.-W.
Cho, Cho, Cho, Cho, Cho, Cho,
D.H. J.H. M.S. S.-D. S.Y. Y.J.
Y.S. Choi, Choi, Choi, Choi, Choi, Choi, Choi,
B.Y. D.S. E. 11. H.G. 1I.Y. J.-11.
Choi, Choi, Choi, Choi,
J.S. J.Y. K.4-I. K.-I.
Choi, K.I.I. Choi, M.C.K. Choi, M.J. Choi, S. Choi, S.-C. Choi, T.-L. Choi, W.-W. Choi, Y.J. Choi, Y.K.
Chongwen, X. Choo, D.J. Choppin, S. Chou, M.-C. Chou. S.-S.P. Chou, T.-C. Chou. W.-C. Chou, Y.-C. Choucair, B.
05, 062 366 219 052, 167, 168, 170, 208, 251, 275, 277, 318, 406, 414, 621 205, 364, 379 308 627 338, 571 397 296, 305, 381, 599 132, 135, 301, 554 327 671, 681 492 380, 705 596 670 014, 188, 329, 627 126 189, 627 007, 451 007, 132, 301, 304, 451 554 022, 023, 030, 053, 056, 549 141 350, 522, 705 225, 411 175, 622, 632 328 260 260, 682 304 012, 122, 174, 222, 368, 492 419 048 031, 154, 345 229 605 417 229 314 280
Choudary, B.M. Choudhary, M.I. Choudhury, P.K. Cho,unan, Y. Chow, J. Chowdari, N.S. Chowdhury, C. Chowdhury, M.A. Chrisman, W. Christensen, C . Christoffers. J. Chrzanowska. M. Chu, C.-M. Chu, C.-Y. Chu, F. Chu, S.-F. Chuche, J. Chueh, L.L. Chui, S.-C. Chun, J.H. Chun, Y.S. Chung, B.Y. ChUIIg, C.-M. C ~ U I IJ.-H. ~, Chung, K.-G. Chung, K.-Y. Chung, S.11. Chung, S.K. Chung, T.-H. Chum. Y . y Chung, Y.M. Churchill, M.R. Churchill, R.M. Ciavnrri, J.P. Ciblat, S. Cicchi, S. Cighetti, G. w t . J.-C Cividino, P. Clapham, B. Clardige, R.P. I Clark, C.G. Clark, D.11.
721
304, 346, 479, 521, 704 275 319, 591 069 001 233 304, 479, 521 493 468 053, 172,410 697 052, 210, 408 274 221 123 316, 338 077 166, 241 657 536 53 1 090 026,029, 062 031, 304 205, 379 393 128 396 627 161 593 054, 438, 671, 676, 678, 679, 681, 684 555 154 658 039 605 474 569 381,582 207 471 448 479 235, 376 242 435 331, 404
722
m k . J.S, Clark, M.A. Clarke, M.L. Clator, E. Claver, C. den. J. Clerici, A. Clifford, A.A. Clinet, J.C. Clique, B. Cohh, A.J.A. Cohley, C.J. Coca, G.P. Coffey, P.E. Cogan, D.A. Cohen, F.
&h!aL
Coin, C. Coindet, C. Colasson, B. Colaux-Castillo, C. Colbry, N.L.
Cole, M.L. Coleman, K. Collet, s. Collier, T.R. Collin. Collins, C.J. Collins, S.K. Colmegna, A. Colucci, M.V. Cornasseto. J.V. Comel, A. Comely, A.C. Comes-Franchini, M. Comins. D.1,. Comoy, C. &lJpJldn. J.M, Confalone, P.N. Conforti, M.L. Connert, R.V. Connon, S.J. Constantieux, T. Conte, v. b j k e . G,
AUTHOR INDEX
578 080 130 70 1 104, 127, 197, 198 59 1 063, 415 464 086 618 024 257 509 352 244, 245 644 179, 216, 499 013 269 059 50 1 267 283 064 096 174 364 206, 613 270, 297 483 27 1 353 585 205, 495, 686 269 672 556 192 499, 523 341, 446, 587, 637, 666 494 004,421, 665 609 21 1 457, 675 196, 199 662 140
Cooper, J.A. Cooper, M.A. C o p h t , C. Coppe, M. coppo, p. Coradin, T.
i2l&mx& C6rdova, A. Corelli. F. Coretz, G.S.
!JxsLlX
Cornelius, L. Correia. CJLR. Corrette, C.P. Corsaro. A. Corsi, M. Cosp, A. cossu, s. cossv. J, Costa, A.M. Costa, I.M. Costa, M. Costantino, U. Costanzo, S. Coskun. N, Cotelle. P. Cottrell, I.F. Courillon, C. Courmarcel, J.
i2uLL
Coutrot, F. Coutrot, P. 1.G C , Couturier, D.
CQmL-E
Couve-Bonnaire, S. cox, c. Cox, J.M. Criunp, S.M. Cremers, J.G.O. Crettaz, R. Crdvisy, C. Crich. D. Cnch. D.X, Cridland, A.
176 231 360 096 375 079 262 625 617 311 521, 610, 667 250 224 438 415 474 330 652 026, 070, 308, 403, 503, 514, 235 083,302 599 310,587 088 271 418 479 154 326 057 060 523 5 23 236 460 159, 304 452 400 246 455 024,033, 647 450 443 022 328 391,537, 579 299, 681 365 552
AUTHOR INDEX
.
.
M.T, Cristau. K.1. Crow L.LJ. Croshy, J. -s.
Cruz, R.P.A. Cruz-Almanza. R. Cseripi-Szhcs, S. Cuadro, A.M. Cuerva, J.M. Cuervo, H. Cuff, A. Cui, D.-M. Cui, S.-C. Cui, W. Cui, X. Cuuico. R.F. Cupone, G. Curci. R. Cuiini. M.
Cursi.R.
Curtis, M.D. Cushnyr, B. Cuzens, J.R. Czerwonka. R. Czira, G. Czopp, M. Czugler, M.
513 422 148 054, 596 048 358,517, 624 015, 160, 378, 502 402 40 1 508 104 449 333, 502 341 250 200 540 507 128, 240 233, 686, 694 370
0.50
083, 085, 088, 109,516, 575, 649 521 473 233, 500 050,403 297 412 552 25 8 194
da Silva, M.F.
Da, C. Da, C.-S. Da, C.-s. Dahdoub. M.J, Dahdouh, V.B. Dabhade, S.K. Daga, M.C. Dahlmann, M. Dahmen, S. Dai, C.
QLG
Dai, J. Dai, L. Dai, L.-X.
Dai, R. Dai. W.-&
Dai huzono, K. Dakamin, M.G. Dale. J.W
Dallaire, C. Dallernagne, P. Dalmolen, J. Dalnozzo. R. Daly, A.M. Damavandi, J.A. Dang, If. Danion-Bougot, R. Dantale, S.W. Darcel, C. Darses, S.
QxdL D'Accolti, I,. D'Addaio, D. D'Amhrosi, A. Annihale. A. I
'
D'Sa, B.
da Costa, R.C. da Rosa, A. da Roza, J.K.
da Silva, F.M.
050 067 355 239 22 1 441,549 305 297 664 210
Das, D. Das, J. Das, K.K.
IhLLL
Das, U. Dauhan. Y, Dauhen. P, Daum G. Dave, B.
723
305 030 022 023 069, 653, 663 069, 663 304 307 446 311,552 145, 179 048 054, 144 043 211, 239, 284, 405, 602 248 025,483 244 478 613 070303 048 405 276 184, 370, 506, 548 349 166 136 59 1 174 174 159, 296 116 323 473 224 075, 313, 418 395 200,544 248 011,311 517 232, 598 258, 259 118 292 236 248
724
AUTHOR INDEX
Daverio, P. David, H. Davidson, F: Davidsson, 0 Davies, A.J.
I.W. Davies, M. Davies, M.K. Davies, M.W. Davies, R.G. Davis. B.& Davis, K.J. pavo11. P. De B a k e r , C. De Buyck, L. De Clercq, J.-P. De Geyter, K. De Giuseppe, S.
De I*a HQLA De Luca, L.
De L-ucchi. 0,
De Meese, J. De Nino, A. de Andrade, L.H. de Armas, J. de Cremiers, I1.A. de Frutos, 6. de Koning, P.D. de la Hoz, A. de la Nava, E.M. dc la Rosa, J.C. de Lange, B. de Leon, S. de Marigorta, E.M.
de Mesnil, F.-X. de 0.Viera, T,
de S6, A.C.P.F. de Saint-Fuscien, C. de Sohns, S.J.
066 046 489 030 064 153, 154, 211, 216, 220, 364, 456, 622, 632, 658 163, 164, 273, 302 537 39 1 670 599 241, 279, 281 282 084, 088 247, 250 490 561,585 603 603 655 382, 603, 615 467 091,387 652 364 184, 370 695 281, 375 140 164 030 165 509 223 276, 565 183 184 592 439 458, 462, 573 459 360 515 363 598 295
de Sousa, S.E. de V.F. Neder, A. de Vincente, J. de Vries, A.H.M. de Vries. J.G. De, A. De, P. De, S. de. Neves, E.A. Deagostino, A. Deak, H.L. DeBms, G.A. DeCarnp, A.E. Declercq, J.-P. DeCorso, A.R. Deganello, G. Degen, H . G . Degin, S.J. Wnnocenti. & Dehli, J.R. deK. Haynes, A.K. Deka, N. del Campo, C. Delacroix, T. Delaney, E. Delapiei-re, G. Delas, C. fileado. 4, Demartis, S. Demay, S. Dernhech, P. Demerseman, B. Demicheli, G. Demko, Z.P. Deng, G.-J.
lkULL Deng, X.-M.
l22QL.x
DeNino, A. Denis, C. Denisenko, A. Denisenko, S.N.
558 402 211,394 196, 199 257,351 413, 500, 639 106 106 123 653 691 065 487 260 530 430,437 351, 353 606 036 058, 066 257 074, 085, 108 101 347,401 252 196, 199 430 032 185 100
071
262 634 706 125, 445, 541, 546,597 513 123 219,375 025, 158 053 497, 630 145, 186, 388 152, 187 511 260,597 548 356 279 279
AUTHOR INDEX
Denisko, O.V.
Depritle, S. Mrien, s. Derrien, N. Desai, B. Desai, P. Desai. IJ.V. Deshmukh, A.R.A.S. Deshmukh, R.R. D e S h o d Deshpande, A.B. Desmarets, C. Desmurs, J.-R. Dessnnti, F. Detomaso, A. Deudon, S. Devasagayaraj, A. Deville, J.P. Devin, P. Dewkar, G.K. Dhao, L. Di Deo, M. Di Maartino, B. di Cosmo. A. Diaha, F. Dias, A.K.B. Dias, E.L Diasa, I1.V.R. D i n , D.D. Diaz, E. Diaz, N. Diaz-Ortis, A. Diaz-Requejo, M.M. Dicdcren, J.J.1 I. L)iedelich F PiGruez. M. Dieleinans, H.J.A.
170 023, 124, 186, 189, 282, 426, 526, 543, 551, 659 480 434, 634, 639, 660 06 1 159 020, 304, 306, 423 256 371 228 459, 696 133, 142, 149, 1.51 418 580, 608, 698 467 290 228 478 379 473 242 149 074 04 1 473, 498 107 368 504 458 242 402 44 1 489 490 482 223 467 165 212 188 484 104, 127, 197 565 169, 180, 571,
Dijksman, A. Dillinger, S. DiMichele, L.
RiluLL Ding, R.
R u L
Ding, 2.4. Dinhus, E.
JXllkJL
Dinsmore, C.J. Dirk, S.M. Discordia, R.P. er. D.C, Diver. S.T, Dix, I. Dixon, D.J. Diakovitch. L Dmitriev, D.E. Dneprovskaia, E. Do, Y.-K. Dijbler, C. Dockendorff, C. Doda, K.
l2sdLuL Dodsworth, D.J. Dohle, W. Doi, M. Dolaine, R. D o h , S. Dolhem, E. Dolling, U.H. Dollinger, L.M. Dorninguez, G.
.. . Donde, Y. Dong, J.
l2QULL
Dong, V.M. Dong, Vy.M. Dong, Y. Dongare, M.K.
725
579 390,392 493 487 027,028 204 485 162 484 25 1 241 473 247 585 430, 433 43 1 429, 434, 612, 634, 639, 660 621 452 525 628 584 390, 501 299 283 311,543 232, 258, 259, 307,598 227, 229 182 608 658 450 399 154 661 226 674, 676, 680, 688 568 29 1 590 294 5 17 584 568 596 314 276, 512, 617
726
Doring, M. LhKiSL
Dormer, P.G. Dorofeev, A S . Doty, M.J. Dou, I L N . Douglas, .I. Dowdy, E.D.
lhYLs-
QLlxkaE Draffen, A.G. Drauz, K.-H.
l2luLL
Droinmi, D. Dronelles, L. Drowns, M. Druiy ILI, W.J. du Mesnil, F.-X. Du, X. Duan, Z.
lhlmLL I2llbu.
Dub&, P. DuBois. J, Ducray, R. Dudiis, J. Duddu, R. Dueno, E.E. Duesler, E. Dueh, W. Duetz, W.A. Duffey, M.O. Dugadina, A.V. Dumas, C. Dumas, J. Dunieunier, R. Dumond, Y.R.
Duncan, D. Dunlap, M.S. Dunn-Dufault, R. Diinnwald, T.
AUTHOR INDEX
45 1 274, 335, 408, 534 163 525,528 639 668 028, 133, 137, 139, 288, 457 371 252 441 264, 387 321, 340 645 352, 354 332 128 647 243 256, 262, 624 4B2 177 167,448 478 243 159, 304 233, 252 190, 499, 694 470 304 248 316,338 220 05 1 050 510,518, 521 700 669 514 171 316, 443 48 1 013, 086, 307, 317, 399, 484, 654 582 642 482 541.546
J2Lumlu Dupuis, C. Dupuis, L.
Durden, D.A. Durst. T. Dussin, G. Dutta, D.K. Dutta, J. Dutta, P. Dwyer, M.P. Dyckman, A.J. Dyke, C.A.
J2Ybss
Dyson, P.J. Dzierba, C.D.
Earnes. J, Earle. M.J, Eash, K.J.
Eastman, T.P. Ehert, H.M. Ehitani, K. Ebrahimian, G.-R. Ehrahimian, G.R. fihavarren. A.M. Eckardt, T. Eckert, C.A. Eckert, M. Echnondson, S.D. Edwards, S.D. Eeckhaut, A. Efimova, I.V. Ehentraut, A. Ehrentmut, A. Eichberger, M. Eikawa, M. Eisler, S.
l2uL.B
El Azab, A S . El Bialy, S.A.A. El-Ghanam, A. El-Hiti, G.A. El-Qisairi, A.
134, 143 139 046 033 282 293 149 442 192, 650 013 413 453, 681, 695 3 10 184,431 161 610
414 466 loo, 108, 110, 410 638 228 096, 110, 362 114 111, 113 432, 460, 660, 691 655 191 390,496 280 464 382 429 142 187 615 102 298, 646 484 298, 633 087 231,468 633 065,373 331
AUTIIOR INDEX
El-Said, N.A.
Elguero, J. Elias, J.S. Elings, J.A. _. Ellensohii, R.M. Elliott, (3.1. ElIis, D.J. Wiian. J.A. Elmali, 0 . Elsenberg, I1.L.M. Emami, J. Emcrschitz, T . Emiabata-Smith, 1). Elninerich, D.J. Enders. D. Endo, M. Eng, 2. Engelhardt, F.C. England, D.B. England, M.D. Enholm. E .J. Enkelmann, V. Enright, M. Enriquez-Kim, V Epifano, F. Epstein, 0.L. Equey, 0. Ericsson, C. Escale, F. Eschavanen. A.M, Escher, 1.11. Escolano, C.
I3scudem-Salas,A.
Eslami, S . b s o n . J.& 1 .
.
529 426, 550 510 468 33 1 33 1 525, 528 686 070, 155 I61 180, 244, 245, 272, 496, 699 627 565 609 039 340 494, 632 311, 396, 508, 708 37 1 326 534 212 560 ox 1 178 066, 325, 382 509 680 288 083, 085, 088, 109, 516, 575, 649 120 64 1 006 260 178 418 372 062 45 2 199 242 214 685 078 10'8, 113 302, 412, 446,
Espino, C.G. Estrella-Jimenez, M. Etemadi, S. Ethiraj, K.S. Etoh, 11. Eustache, F. Evano, G .
Evamere, K. Eymery, F. J.J.V. Ezooe, A.
w.
Fahhrini, M. Fahi-izi, G. Fache, F. Fscke, T. Fadaei, 2. Fagnoni, M. Fagnou, K. Faja, M. Fakoorpour, M. Falck. J.R. FalguiCres, A. Fallon, L. Falomi. M. Familoni, OB. Fan, C.-A. Fan, J.-F. Fan. 0.-11. FaiionBs, R. Fang, G. J.-M. Fang, J.-Y. Fang, L. Fang, W.-K.
727
523 455 233, 252 454,532 102 689 608 503 452 485, 620 252, 253, 321, 344, 580, 672 322, 323 703 335 04 1, 505
092 208, 233, 466, 616, 640 249, 283 635 312 375 452,526 552 083 093 034, 081, 108, 139, 338, 558, 571 026 1 1 8,439, 483 073 018 232 542, 668 529 025, 158 487 238 317, 318, 417, 502 442 210 303
AUTHOR INDEX
728
Fang, Y. Fantin, G . Faraone, F. Farcas, S. Farhadi, S. F h e g h d h , K. Fai~ell,B. Farrokhi, A. Farshidipoor, S . Fasihi, J. Fassina, V. Flssler, R. Faure, R. Faurk-Trmneur, M. Favi, G . Favier, I. Fazio, A. Fazzolari, E. FedC, J.-M. Fedeiuv, A.Yu. Feducovich, S.K. Feglevich, G. Fei ten, 1-1.-J. Felix, L.dc A. Feng, A. F C I I ~L.-C. , Feng, Y. Feng, Y . 3 . Fensterhacnk, L. Fenton, G . Fenwick, D.R. Ferencic, M. Femandes, B.C.M. Femandez, D. Fernindez, A. Fernindez, I. Feniindez, M. Fernindez, J.-C. Feniindez-Acehes, A. Femindez-Fano, R. FernhickzHernandez, J.M. Femdiidez-Mateos. 4. Fernindez-Rivas, C. Femindz, I.
038, 389, 458, 517, 570,571 047, 413, 580 35 1 128, 199 166,512, 584 120
503
307 092 080 230, 326 462 486, 488 677 444 248 013 169, 699 445, 533 224 341, 279 525,528 194 050, 051 112 639 043 521,538,545 056, 057 013, 026, 540, 543, 551 04 1 279, 281 370 03 1 196, 197, 199, 359, 452 357 220 214 068 286 2x3 218 341 171 509 432 412
Feroci. M. Ferrahoschi, P. Fenara, M. Ferraris, D. H.M.C, Ferreira, E.M. Ferreira, F. Ferreira, J.T.B. Ferribres, V. Ferroud, C. Ferwanah, A. -R .S. Fettouhi, M. Feuerstein, M. Fey, T. Fiaschi, R. Fiaud. J.-C, Fiedler, C. Field, J.A. Fieldhouse, R. Fielding, M.R. Fields, J.D. Figueras, F. Figueredo, M. Filho, E.P.S. Filik, R.P. Filimonov, V.D. Finch, €1. Finet. J.-PL Fiorini, D.
Fischer, C. Fischer, H. Fischer, R. Fitzjohn, S. Flack, K. Flaherty, A. Flammang, R. Flanders, V.L. Flaniken, J.M.
Fleury, M.-B. Flood, R.W.
248, 263,338 073 238,240 256 360, 641 201 184 069 356 026 147 633 133, 137, 139, 288,457 091,096 652 400 462 064 218, 234 063,548 282, 362 704 592 157 376 372 629 279, 341 258 481, 671 078, 092, 093, 102, 108, 109, 110, 111, 113, 114, 305, 364, 367, 475, 476, 480,703 327,488 091 635 054 460 589 468 222, 234 270 415, 439, 550, 669 007,439 307 354
AUTHOR INDEX
Ploreancie. P.& Flows, A.F.C. Flores-Santos, L. Florey, P. F16rez. J. Florio, S. Floyd, R.J.
ElwLBL
Fochi, M. & g a ~ n o l o M. . Fokin. A.A. Folest, J.C. Fong, W.M. Font, J. Fontaine. Fontana, F. Fonteneau, N. Ford, A. Ford, J.G. Forget-Champagne, D. Forgione, P. Foiman, G.S. Forni, A. Forrester, M.T.
EsLx
Fortunak. J.M. Foster, A.C. Foster, K. Foster, K.1,. Foli, C.J. ~ o u h e l o .F.
Fournioux, X. Founey, J.-L. Fox, J.M. Fox, R.J. Fracchiolla, G. Fraile, J.M. Francib, (3.
W.
Franco, D. Francoeur, S . Frank, K.E. Frantz, D.
524 297 127 06 1 218 246 276,508, 549 222 462, 654 556 35 1 371, 374 512 399 491 592 275 092 183 062 465, 684 183 118,439 160 247 074 031, 122, 139, 141, 154, 290, 345, 382 004, 005, 06 1, 665 62 1 26 1 086 362 271, 319, 507, 508, 591 126 148 153, 407 602 482 215, 674 199 246 086,307, 317 213, 216 238 016,334 486
Frantz, D.E. FrBnzl, H. Freccero, M. Freiherg, D.A. Freifeld, I. Freitag, R.A. Frejd, T. French, A.N. Frenette, R. Frkre, S. Fretwell, P. Frey, D. Frey, D.A. Frid, M. Friend, C.L.
Frison, J.-C. Frolich, R. Frontier, A.J. Frost. C.G, Frost, T.M. 11.-W. Frullanti, B.
l3x-LL Fu, F.
l3LJ3.L
Fu, H. Fu, I.-P. Fu, Y. Fu, Z.
Fuchs, J.R. Fugami, K. Fuganti, C. Fujihaa, 1% Fujii, A. Fujii, €I. Fujii, K. Fujii, M.
729
072, 486, 488, 577 096 375 078 212 297 463 62 1 651 314 589 075 465 149 092 333 620 273, 619 045, 074, 302, 467,532 623 551 659 087, 402, 411, 48 1 170 188 635 205, 273, 377, 384 128 002, 040, 141, 145, 179, 190, 449, 456, 464, 643, 672 106,418 055, 057 492 180,650 002, 269, 297, 344 508,560 177 163 242 630 364 336, 598 059 035, 569, 590,
730
Fujii, S . Fujii, T. Fujii, Y. Fujikura, R. Fujimatsu, H. Fujimoto, K. Fujimura, Y. Fujioka, H. Fujioka, S. Fujioka, Y. Fujisaki, S. Fujisawa, 1-1. Fujisawa, N. Fujita, A. Fujita, K. Fujita, K.-i. Fujita, M. Fujita, N.
JLulbJ
Fujiwara, 1-1. Fujiwara, M. Fujiwara, N. Fujiwara, T.
Fukisawa, N. Fukita, S . Fukuda, K. Fukuda, M. Fukuda, T. Fukuda, Y. Fukuhara, H . Fukuharu, T. Fukui, M. Fukumachi, S. Fukumoto, Y. Fukuoka, K. Fukuoka, Y. Fukuta, Y. Fukuta, Y. Fukuyama, T. Fukuzawa, S-1. Fun, N. Funakoshi, S .
AUTHOR INDEX
619 553 218 348 320 04 1 663 343 495 398 33 1 538 497 132, 608 204 193 363, 509, 626 122 097,437,665 412 025, 027,125, 126, 127, 129, 130 182, 437, 666, 702 015 437 214, 216, 433, 451, 462, 467, 615, 653 01 1, 014, 434, 435, 466, 592 626 135 078 339 127, 173, 457 099 245 370, 662, 368 61 1 317 173, 331, 672 452 476 564 633 404 054 699 519, 628
Funasaka, S. Fung, S.1I.C. Funk, L.
. .
Furkawa, A. Fumess, K. Fumess, K.
Furugaki, H. Fluukawa. Id
Furuma, T. Furusawa, Y. Furuya, T. Fusco, C. Futiunura, J.
Gahriele. B. Gadhwal, S Gadras, A.
Gagnier, S.V. Gajare, A.S. Galahi, S. Galindo, A. Galka, A.M. Gallaagher, W.P. Gallagher, M.E. Gallagher, W.P. Gdla11d, J.-C. Gallardo, I. Galletero, S.
GaILG
Galli, E. Galluzzo, D.J. GaloniC, D. Giuna,Y. Giunber, G.G. Ganchegui, B. Gandon, V.
641 49 1 415 560 398 256 257 004, 213, 456, 695 348 044, 608 038 664 050 050 398
037, 136, 402, 403, 467, 489, 128, 288,
169, 310, 587, 661 029, 338, 384, 606 422 193,551 636 314
322
660 626 435 325 427 453 294,295 412 092 353 661 538,541 618 677 380 216, 217, 278, 588 080
AUTHOR INDEX
(ianesh, Y.S.S.
088, 305, 659 106 526, 554 Gao, F. 700 Gao, G. 325, 426 Gao, 1-1. 360 Gao, J. 680 Gao, J.J. 554 Gao, s. 420 Gao, w. 656 Gao, w.-%. 171 Ciao, 015, 036, 084 Garcia, C. 204 Garcia, G.V. 393 Garcia, J.I. 215 Garcia, M.C. 705 Garcia-Gnrihnv. M .4 136 Garcia-Gcimez, G. 675 Garcia-Martin, M A . 56 1 371 Garciu-Zayas, E.A. 496 Gayon, s. 163 Garg, P. 100 Gamctt, I. 363 400 Gairido, F. Giirtner, P. 03 1 Carvey, D.S. 389, 517 Gary, T. 480 Gaspairini, F. 208,466 Gaspnrski, C.M. 646 Gastner, T. 277 Gathergood, N. 531, 540, 570, 571 021, 025, 027, 549 Gaunt, M.J. 570, 577 Gautheron-Chapoulaud, V. 47 1 Gauthicr Jr., D.R. 021 Gautier, A. 086, 097, 112 Gauvry, N. 482, 499 Gavryushin, A.E. 475 Geis, 0. 285 Geislcer, V.J. 480 Celalcha, F.G. 391 Geller, T. 355 Gellihert, I;. 368 Genet. J.-P. 054, 139, 224, 453 Geng, F. 049, 389 04 1 004
x.
Genski,T. Gentili, P. Gentilucci, L. Geoffroy, O.J. Georc. G.& George, T.G.
Gerasyuto, A.I. Gcqek, Z. Geresh. S, Gerrits, P.J. Gesenherg, K.D. Geslin, M. Gessler, S.
Gettwert, V.J.
Ghaemi, E. Ghaffmadeh, M. Ghagare, M.G. Ghassemzadeh, M. Ghatak, A.
shdfLI2
Ghodrati, K. Gholizadeh, M. Ghorai, B.K. Ghorbani, M. Ghosh. A.K. Ghosh, K. Ghosh, S.K. Gianeti, T.R. Gianotti, M. Gihhins, T. Gibson, J.M. Gibson. S.E. Giehel, D. Gierczak, A.H. Giese, B. Giese, S.
W'
73 1
365 092 241, 596 379 098 376, 662, 705 205 167, 606 597 569 548 663 275 456,463 183 478 115, 118, 121, 129, 173, 394, 436, 493, 559, 611 473,477,479 278 304 079, 088, 096, 099, 100, 101, 107, 108, 112 095, 507,576 561, 585 048, 107, 372, 423 242, 413 092 536 358 069,523 388, 411 526 091, 387 131, 236 653 241, 596 154 479 020 467, 672 402, 403 689 513 187 377
732
AUTHOR INDEX
Gil, G.S. Gil, J.M. Gil, M.V. Gil, R. Gil, S. Gilardi, R.D. Gilhert, B.C. Gilhert.;on S & Giles, P.R. GiIlespie, K.M.
Giordano, L. Giorgio, E. Giovannini, R.
28 1 692 67 1 209, 463 009, 229, 499 248 083, 152, 575 180, 650, 651 097 354 349 215 090 048 359 024 149 313 260
u.
Giridhar, D. Girotti, R.
Giurg, M. Giuseppone, N. Glapski, C. Glass. R.S. Glasson, S.R. Gleason, J.D. Glorius, F. Glover, B . Goacoleu, K. Gohle, M.P. Gii@iann, M. Goddard, J.-P. Godfroid, J.J. Goeldner. h.1. Goerlich, J.R. Goggiamuni, A. Gogoll, A.
Gogonas,
E.P.
Goh, S.-€1. Giiksu, S. Gold, M.R. Coldfuss, B. Golding, B.T. Goldsmith, M.D. Golihski, J. Gornes, A.K.
415
023, 519 014 015, 016 206 600 257 606 610 427, 658 490, 673 153, 445,465 134 363 012 488 072 101 076 489 233 006 656 522 105 316 07 1 017 578 473 210
Comes, P. Goinez, L.
207 368 086, 127 G6mez-Bengoa, E. 338 Gbmez-Escalonilla, M.J. 136 G6mez-Lara. J. 685 Cbmez-Vidal, J.A. 074 Gomis, J., 046 Giimiiry, A. 104 606, 642 Gonplves, S.M.C. 363,548 Gondai, T . 191 Gong, H. 313,414 Gong, J.11. 165 Gong, L. 128 Gong, Y. 146 Gonsalves, A.M.d'A.R. 301 Gonzalez, A.M. 192 GonzBlez, E. 499 Gonzhlez, G. 371 Gonziilez, J.M. 561 214 Gonziilez, R.R. 509 Gonzlilez-Bobs, F. 561 Goolien. I ,..IL 141, 147, 388, 41 1 Good, G.M. 635 Gopalaiah, K. 260 Gopinath, R. 076, 126, 318 Goralski, C.T. 297 040 Gordon, G . 215 Gordon, G.J. 23 1 Gordon, P.E. 377 614 i&BL!& Gorgojo, J.M. 487 Gorls, H. 45 1 Gorsuch, S. 287 Gosain, R. 245 Gosherg, A. 194 129, 207 Goswami, A. 018 Gotanda, K. 644 Gothelf, A S . 025 Gothelf, K.V. 699, 701 Goti. A. 262,474 Goto, K. 038 Goto, M. 707 Goto, T. 598 Gotor. V. 056, 058,066 Gottardo, C. 088
AUTHOR INDEX
Giittlich. R . Gottschalk, T. Goud, P.R. Goudarzi, M. Gourevitch, D.N. Gouverneur. V, Govande, V.V. Gowda, A.S.P. cla. D.C. Gowda, s. Gozzi, C. Grahowski, E.J.J. Gradel, B. Graff, A. Graney, S.D. Grasa, G . Grasa, G.A. Grasso, C.A.
cAaLM.
Graziano, M.L. Grazini, M.V.A. Grie. R. Green, A.I. Green, B. Green, M.P. Greenman, K.L. Greenspoon, N. Greeves. N. Grega, K.C.
Greeorv.R.J.H. Greidanus, G. Grcig, I.R. Grenicr, J.-L. Grihhle. G.W. Gridnev. I.D. Grieco. P.A. Griera, R.
&esheck. A.G, W.P.
Grigoropoulou, G. Grimin, C. Grimin, M.L. _.. Grogan, M.J. Griieer. H.
533, 603, 604 552 419, 420 003 219 037 3 32 228 305 305,306 305 140, 143, 249 010,577 290 635 114 185 292 008, 133, 289 285 147 325 622 390, 391, 537, 579 626 648, 649 584 448 569 549 014 562 412 5x3 458 479 143 192 085,334, 618 397, 604 340, 514 495 558, 587, 589, 637, 658 404 269 394 523 610 547
733
Gronheid, R. Gros, P.
Groth, U.M. &oth.U, Grover, P.T. Grover, V. Q u h h s . &fL Grutladauria. M . Gstiittmayr, C.W.K. Gu, s. Gu, Y. Guan, €I. G u n , X.-P. i3.UnL Guangyong, X. Guari, Y. Guarna, A. Guchhait, S.K. Guemik, S. Guerra, F.M.
fiukl.
GuihB-Jampel, E. Guichun, Z. Guijarro, D. Guilard. R, Guillen, F. Guillerez, M.-G. Guin, C. Guiso. M. Guizzardo, B. Gujadhur, R. Gujadhur, R.K. Gulea, M. Gulyb, H. Gunanathan, C. Gunasekar, D. Gunchenko, P.A.
Guo, H. M.-P. Guo, Q. Guo, W.-r. Guo,
x.
GULL
Gupta, A. Gupta, M.
mlLL
665 031, 122, 154, 345 28 1 503 629 313 175, 456, 461, 620, 622, 632 526, 430, 437 141 375 155 45 1 248 028 419 293 581, 616 192,371, 650 569 312, 495 046, 429 287 095 185 293 195, 196 046 366, 371, 642 336 375 347 276 127 104 109,406 525 37 1 685 028,422 706 119,325 66 1 216, 539 018, 102, 232, 252 327 103 103, 678
734
AUTIIOR INDEX
Guram. A S , Gurunath, S. Guth, 0. GutiCirez-POrcz, R. Guv. R.K. Guzei, I. Guziec Jr.. F.S. Guzman, A.
293 014 004 685 338 440 378 482
&. D.-C.
513 136, 596, 625 550 264, 387 075, 077, 109, 120, 475 100, 107 317 277, 283 104 388 567 376
~ aIr.-J. , Ha, Y.-11. IIaak, E.
llaliihi. M.H.
Hahihzadeh, S . IIabu, II. IIackfeld, L. Iiackstell, R. Hadden, M. IIaddleton, D.M. 1IadjiantoniouMaroulis, C.P. ~
. . O..
P
IIafcz, A.M. €Iaga, M.-a. Jiase. A. Ilage, R.
IIagiwara, N. Uahinour. A.R. IIair, C.M. IIajara, A. IIajdu, C. JIaiipour. A . R IIajra, A.
Ilaira. S .
Jlakipour. A.R. Hakoda, K. Halhcs, U.
I
279 O656 ~ 262, 624 613 064 359 354 183, 210, 457, 528, 562 177 096 151 079 060 019, 092, 095, 096, 098, 099, 106, 414 079, 171, 571, 696, 702 39 1 411 183 005, 494
IJales, N.J. IIalford,B.A. Halland, N. Hallher-
Halle, R.T. Hamada, T. IIamaguchi, II. IIamamoto, H. IIananaka, N. Hamasaki, R. IIamashima, Y. IIamed, 0. Hamilton, G.S. Hamniond, M.E.W. IIampel, N. Han, E.-H. Iran, G. Man, J.-S. Han, J.K. Han, J.W.
Iran. I..-B. Han, R.
Han, S.-Y. €Ian, S.W. Han, X. Man, Y. €Ian, z.
€Ian, Z.P. IIanai, M. Hanaki, N.
Hanamoto.,
JIanaoka. M. Handy, C.J.
Hang, J.-F. Hannan, J.J.
Hansch, M. ILnsen, K.B. Hansen, M.C. Hansen, T. Hanson. P . s Hanya, N. Hao, C.-J.
672 331 597 399, 460, 610, 617 184 050,059 352,534, 612 082, 125, 336, 514 511 398 569 069, 544, 628 548, 647, 648 269, 331 013 373 153 513 587 135 384 430,432 705,706,707 261, 277 003, 682 090 631, 639 014, 042, 210 511, 530, 531, 534 487 548 468 182,565 413, 687,702 142 177, 258 571 056 205 539 530 280 025, 154, 197 243 025, 027 400, 546, 605, 673 363
AUTI IOR INDEX
Hao, J. Hao, S.
€fuxL
IIapase, S.B. Har, D. Hara, N. IIaru, 0.
LIiuLL IIara.
s.
Iiara, T. I-Iarada, K. Harada, Y. .. fiaravarna. I . Harcken, C. Hardouin, C. IIari, A. Harigaya, Y. IIarikishan, K. IIaritha, Y. Harkins, S.B. Jlannata. M H a m s , K. Iiannsen, D. IIarnett, .J.J. Harre, M. I Iairing ton, P.E. Ilairis, C.L. Iiairis, M.C. Ilanis, W. Hairison, C.L. IIairison, J.R. IIilmity, J.P.A.
m.J.F.
~ l l ~ w v e 1J.C. n .
Harlley, J.P. IIartinann, B. Hartung, C.G.
Harwood, S.J. IIas-Becker, S. Iiase, E.
034, 556 571 025 306 308 250 125, 336,514 119, 325, 383, 483 370, 662 518 539 058, 433, 497, 626 682 346, 364 440 335,534 306 248 285 383 455 69 1 575 05 1 274 162 589 172, 410 075, 243 282, 285, 291 176 204 154, 262, 357 316, 585, 670 503 370 402, 481 39 1 163, 650 264, 298, 466, 615 396 232, 289, 292, 321, 408 638 44 1 507 525
735
I-Iase, T.A. Hasegawa, H. IIasegawa, J. Hasegawa, Y. Hashemi. M.& Hashemzadeh, M. Iiashim, S.R. Hashimoto, K. Jiashimoto. S. Jlashnnoto. Y. Hashini. A.S.K. Haslinger, U. Hassan, J. Hassib, L. IIata, Si. Hata, S . JIata, T. Hatakevarna. S. I-Iatanuka, K. IIatano, B. Hatano, K. Hatano, M. Hathrouhi, C. IIatta, G.
.
.
Ilattori, K. IIattori, R. Hauck, S.I. Hauptman, E. JIauske. J.R. Hawryluk, N.A. Hayakawa, N. Hayakawa, R. Hayakawa, S. IIayakawa, T. Erayakawa, Y. Iiayasaka, S.
IIayashi, S.
I layashida, T. IIayat, s.
077 538 287 056 609 084, 105 661, 679 082, 641 357,391, 688 623 658, 683 170 028 140, 143 599 476 126 348 040, 559 273 122, 510 125 034,556 140, 143 359 317 063,161 502, 510 292 242 649 324 336 065, 342, 364, 508, 524, 538, 579, 600, 676 080 476 132 475 076, 079, 157, 158, 539, 658, 683 126 185, 194, 200, 201, 211, 236, 239, 428, 430, 631, 632, 668, 678 01 1 275
736
Ilayen, A. Hays, D.S. Hayter, B.R. I-Iazarkhani. H. Hazell. R.G. IIha’ieh, S. He, 11.-Y. He, L. He, Q.-W.
He, s.
He, Y.
Hebhe, V . Jkck. M.-P. Heckrodt, T. Heckroth, 11. Hedhli, A. Hedley, S.J. V.B. rJegde, V.R. Hegedus, C. Heiermann, J. Heiss, C. Helion, F. HeIliweII, M. Hemenway, M.S. Hemmerling, M. Hemmerling, M. Hems, W. Hems, W.P. IIen, J. Henderson, J.C. HCnique, J. Henkel, G. Hennings, D.D. JIenrv. P.M. Henryon, V. IIeras, Md.R.C.
Herh, B.R. IIerhert, M.
AUTHOR INDEX
209 382,584 040 360 093, 109, 110, 111 202,531, 565, 571,580, 600 619 240,252 624,668 705 238 028 010 23 1 047,651 162 514 517 585 264 362 104 in4 486 079,505 070 276,512 699 349 357 604 058 160 491 473 079 431 490 150 33 1 342 145 079,088,089, 096,097,098, 099, 100, 101, 102, 107, 108, 112,412,505 048 050, 403
Herderich, M. Herdtweck, E. Herihanovh, A. Hennann.W.& Hennanns, N. Hermsen, P.J. Henihdez, R.
€skm&dx
Heron, N.M. Heirador, M.M. Herradura, P.S. IIerreriaS, C.I. Hemnton, P.M. Herrlich, M.
Herscovici, J. Herz, €I.-G. Herzherg, D. IIerzig, D. Hesse, s. Heuft, M.A. Hewitt, G.W.
€immLiE Heydari, R. IIibhs, D. Hibbs, D.E. Hicks, F.A. Hicks, L.D. Hida, K. Hideura, D. Hiehert, S. Hiemstra. H, Higashi, N. IIigashino, T.
lliLwL
Hikasa, S. Hilagenkamp, R. Hildehrand, J. Hildehrand, J.P. IIilgenkamp, R. HiIIier, A.C. IIillier, M.C. &hersson. G.
Hiui
IIindupur, R.M. Hino, H.
391 568 384 141 021, 026 022 474,560 118, 165,536 316 502 338 215 646 153 003 313 425 058 420 140 368 186 701 609,700 475,480 568 574 295 384 062 300, 491,494 679 555,557 188,453,586, 591 670 192 409,564 467,602 442 662 095 021,026 578,626 133 035 030 459,462 076 252,682
AUTHOR INDEX
Ilino, N. IIinterding, K. IIioki, K. Hirahayashi, K. I-Iirabayashi, K IIirai, C. IIiraike, €1. Hiraiwa, Y. IIirama, M. Iliramoto, K. Hirano, 1-1. IIirano, J. Hirano, K. Ilirano. M. I Iirano, T.
JJlLLL
IIirmka, M. IIiraoka, S . IIirasaka, Y. Nirashita, T. IIirata, N. IIiratsuka, Y. IIirayamil, K. Ilirayama. Y. IIirose, M. Hirota. K. IIirota, T. Ilirt, u.11.
110, c.-Y. 110, I-.-M. 110, M.M.
JIo. T.-I.
,
&&,&J.J,
son. r ) a 1 %
IIodgson, P.B. IIoen, R. Jioffinann. I I .M .R . Iioffinann, K.J.
562 523 486 002, 150, 177, 185, 484 273, 284 407 25 1 082, 536 442 315 079 320 520 066, 094, 160, 412, 559 159, 338 016, 105, 133, 208, 223, 508, 510, 621, 690 654 232,429 080 032,506 135,539 191, 398 190 500, 694 476 190, 676 306 063, 161 412 62 1 063, 089, 150, 185, 193, 348, 369, 459, 484, 675, 683, 694 350 350 304 122 03 1 337 046, 160, 345 578 137 083 374 600
Hoffmann, R.W. Hoffmann-Rocler, A. Hofslokksen, N.U. I Iogenauer, K. Hojo, M. IIolbrey, J.D. Hollmann, C. Holmes, I.P. IIolody, w. Ilolz, J. Holzapfel, C.W. Halzer, B . Nomma, M. Homsi, F. €Ion, S.-W.
HJmdLL
Hondo, T.
m
Hong, J.-B. IIong, R. IIong, S.D. IIong, Y .-T.
JIoneo. H. IIook, D.F. Hope, E.G.
IiQlwa
IIoraguchi, T. Ilori, H. IIori, K. IIori, N. IIori, R. IIorie, Y. Horiguchi, S . Ilorino, H. Horino, Y.
Ilorvdth, A. Itoshi, T. IIoshino, Y.
IIosoya, H. Iiossain, K.M. &ssain. Ilosseinnia, A.
737
227,300 211, 651, 656 103 67 1 429 466 646 394,549 482 158 323 300 344 173 313 3 14 251,346, 522 239 286 396 137 544 002, 223, 399, 553 02 1 147 561 043, 551 050,074 456 566 629 242 658 034 069 037, 406, 563 623, 624 664 665 183, 210, 457, 528, 562 003, 674, 688 353, 528 202, 204, 239, 267, 429, 506, 626 406 223 628 206
738
AUTHOR INDEX
Ilou, D.
Hou, Y.
HSmL
Houpis, I.N. Houser, J.H.
Howarth. J. Iiowell. A.R.
I.iYYdx
EIraFhak, M.J. Hrshowitz, M.
flsiao.
Y.
IIsieh, S.-€-I. Hsu J.-L. rru, B. IIU, c. HU,
c.-c.
Hu, 11. Hu, J.-h.
u
kIu, Q.-Y. IIu, R.-11.
IIU,
s.
IIU,
x.
Hu, S.-R. Ilu, T.
Hu,
w.
u Hua, K. Iiuang w.4. IIuang, A. IIuang, D. Huang, D.-R. Iluang, II. I-luang, 11.-L. IIuang, .I. Iluang, J.-M. IIuang, J . 3 . IIuang, L.-C. Iluang, Q.
065 239, 284, 405, 602 580 181 290 460 266, 272, 281, 375, 454, 460, 465,610 OS4, 144 093, 545, 618, 661, 679 447 549 569 299 02 1 317, 318, 417 167, 488, 489, 606 010, 308 213 326 599 162 234, 305, 585 175,336, 341 390 354 221 190 340 20 I 224, 387, 492, 561, 599, 631, 662, 690 62 1 029 669 492 123 659 064, 6 12 289, 292 522 255 015 5 u 115
h a n g , T. Huang, T.-B. Huang, T.-N. Huang, T . 4 . Huang, W.-S.
IAliuL
h a n g , Y. Huang, Y.-P. IIuang, 2. fhang, 2 . Z Huher, F.A.M. Hueft, M.A. Huerta, F.F. Huertas, I.
HwLL
IIughes, D. Hughes, D.D. Hughes, D.L. Huh, H. Huh, S.C. Hum, Y.-J. Hummel, W. Humphrey, J.M. Humphries, M.E IIunderhnark, T. Hung, C.C. Hungerhoff, B. Hunt, K.W. Hunter, A.D. Hunter, C. Hunter, J.A. IIunter, R. Hnrosawa. ri; Hursthouse, M.B. Huitado, G.R. IIusfeld, C.O. Hussaiu, I. Hutta, D.A. IIuynh, T. Hwang, H.-J. Hwang, J.-W. Nwang, J.P. Hwang, S.H. JIwu. J.R.
598 265 568 202, 203 556 272, 290, 347, 364, 407, 492, 624, 637, 661, 666, 706,707 562 476 042, 210 413 634 516 075 483 130, 519 294 499 163, 302 613 299 595,597 195, 703 077 486 581 130 002,396 605 280 334 602 29 1 115 360 428 568 653 465, 6x1 022 303 288 38 1 584 398 683 536
299, 365, 493, 655, 705,
AUTHOR INDEX
Hveon. T Hynd, G. Hyodo, M. Hyund, G.
Iacazio, G. Iawa, M. Ihrahhn-Ouali, M. Ibrahlmzade, N.
LtukLx
Ichiguchi, T. Jchihnra. 1, Ichikawa, H. Ichikawa, T. Ida, Y. Ide, M. Ide, N.D. Iding, H. Ie, Y. Igantcnko, A.V. Igarashi, K.
Igarashi, M. Iglesias, B. Ignatenko, A.V. Iguchi, Y. Ihara. M . Iida, D.
Ilkx IkwdL Ikeda, 11.
IkulLW
Ikeda, S. Jkedil. S.-1. Ikeda, T. Ikegashira, K. Ikeno, T. I
.
Ikonnikov, N.S.
u
Ilangovan, A. Ilankum;iran, P. Illy-Cheney, S.
351, 676, 679 218, 238, 654 011,474 341
055 455 325 597 024, 035, 442, 590, 619 442 356 337, 487 263 059 182 512 546 379, 404 283 504, 505, 547, 641 269,344 184 269 203 183, 655, 673, 674 093 102, 533, 607 057, 060, 143, 328, 401, 501, 521, 542 631, 632 237, 244, 468 298, 654 117, 172, 200 274, 435 484, 694 193, 213, 357, 391, 535, 552 600, 648, 649 162,564 087, 553 087,324 139, 141, 382
Ilyina, N.A. Im, D.S. hn, J.-M. hn, Y.J.
Lnagawa. H. Lnai, Y. b o t o . Imamoto, Y. Lnanzadeh, G. Lnboden, C. Imbos, R. b h o f . W, Inaha, Y . Inada, K. Inagaki, M. Inagaki, S. Ince, S.J.
In6Si.A
Ingalls, C.L. Inoh, 1.-I. Inotsume, T. Inoue, A. Inoue, 11. Inoue, K. Inoue, M. Inoue, K.
IixucL Jonin. B.I. Iorga, B . Ipaktschi, J. Irandoost, M. Irannoor. N.
Irie, M.
Irk,R.
-1 Isakov, V.E.
Iseki, K.
739
646 031 410 165 676 406 159, 192, 298, 521 510 096 469 199 588 157 144 474 013, 049,388 5 65 621 254, 327 248, 263,338 192 184 290 528 049, 144, 346, 400,509 425, 435 090, 381, 388, 428 149, 315 146 135, 245, 459, 640 700 703 268 345,526 048, 088, 109, 110, 111, 113, 114, 346, 367, 424, 475, 480, 549, 644, 703 434 092, 217, 218, 219,352, 527 395 120 03 1 532
740
Ishiha, A. Ishida, A. Ishida, 13. Ishida, T. Ishigedani, M. Ishihara, 11. Ishihara, K. Ishihara, T. Ishii, A. Ishii, D. Jshii. & Jshii. Y.
Ishikawa, F. Ishikawa, S. Jshikawa. T
Ishitani. 11. Ishiwata, A. Ishivainaim. T. . . Ishlzaki. M Isohe, 11. Isohe, T. Isono, Y. Isozaki, S. Itagaki, Y. Itami, K.
Ito, A. Ito, fI. LkLL Ito, M. Ito, s. Ito, T.
AUTHOR INDEX
02 1 244, 622 344 67 1 500, 647 236, 239 566 082, 189, 227, 520, 536, 544 430 335 516 610 014, 051, 097, 101, 102, 174, 191, 300, 358, 359, 383, 391, 393, 408, 409, 478, 491, 497, 518, 520, 564, 602, 623, 630, 643 251,346 334 313, 061, 078, 162, 368, 455, 564, 611 152 579 082, 336, 341, 626, 660 277, 288, 520, 522, 606, 609 655 396 003, 674, 688 446 078, 313, 368 574 478 337 142, 180, 271, 687 040 328, 535, 543 126 131,444 507, 654 040, 134, 156, 234
Jto. Y.
Jver. S. Iyigiin, C.
034, 058, 173, 687 566 225, 656 013, 049, 093, 388 117, 119, 219, 450, 455, 491, 510, 564, 583, 590, 633, 637, 679 502 597 607 702 203, 209 040, 559 051, 358, 359, 391. 393, 408, 518,520 674, 688 626 040,286 150 574 249, 581 034 501 127,457 021 215,328 065, 081, 273 326 427 316 641, 644 297 538 433 044, 073, 084, 085, 086, 101, 265, 301, 303, 305, 530 185, 585, 638 627
Jaber, J.J. Jaber, N.
642 6 13
IhLILJ
Itohara, S. Itonaga, M. Itono, Y. Itooka, R. Iwabuchi, Y Iwahama, T. Iwahara, K. Iwai, H. Iwai, J. Iwama, T. Iwamatsu, S.-i. Iwamoto, K. Iwanami, T. Iwane, €1.
IxaLM.
Iwasa, K. Iwasa, s. Iwasaki, F. Iwasaki, T. Iwashita, S. Iwata, A. Iwatani, K. Iwaya, K. Iwazaki, K. Jvenear. D.S.
AUTHOR INDEX
Jahin. I. Jackson. R .F.W, Jxkson. .. R.W, Jackson, T.J.
R
Jacoh, J. Jacoh, R.G. Jacohsen. E.N. Jacques, 0. Jacquot, R . Jadhav, V.K. Jagadeshwar, V. Jagannadh, B. Jagtap, 1-1. Jain, R.1’. Jalil, A.A. James, B.R. James, P. Jamieson, J.Y. h s o n . T.E Jan, D. Jana, U. Janes, M.K. Janeshwilra, G.K. Jang. D.O. Jang, T.-S. Jang, w.11. Jang, Y.-.I. Jankowska, R. Jansat, s. Jansen, A. Jmahpour, A.A. Jasiinghani, H.G. Jasinski, J.P. Jasra, R.V. Jayakumar, K.N. Jayalakshini, B. Jayaprakash, K. Jayasree, S. Jeevananclam, A. Jefferies, L. Jefferv. ‘r, Jekd, J. Jen, W.S. Jennings, J.M. Jensen, A X .
58 1 291, 353 012 165 287,363 446 069 286, 501, 523, 530, 648 353 283 414 700 601 473 646 138 160 054, 144 454 556 219 085, 171, 571, 702 625, 636 314 580 009, 205, 229, 344, 364 003, 682 432 22 I 048 127 615 102 287 519 3.50, 351 124 420 619 016 163, 172, 594 386 448 060 561 649, 689 020 150
Jensen, K.BV Jeon, 1.1.3. Jeon, M. Jeong, B.-S. Jeong, B.-s. Jeong, I-I.J.
u Jeske, M.
Jesson. P.G. Jew. s.-s, JCz6que1, M. Jha, S.C.
u
Ji, M. Ji, S.-J. Jia, C. Jia, L. Jia, Y. Jia, Y.-X.
Jiang, J.-K. Jiang, L.11. Jiang, P. Jiang, W. Jiang, Y.-Z. Jiao, X.11. Jim@nez-Estrdda,M. JimBnez-Tenorio, M. Jimeno, C. Jin, C. Jin, C.K. Jin, F. Jin, M. Jin, Q. Jin, T. b.T.-S. Jin, W. Jin, X. Jin, Y.S. JULz
Jinnai, T. Jireensons. 4 . Jnaneshwara, G.K.
741
202 258 559 597 595 043 682, 683 503 160, 474, 191 595,597 449 197 210 705 623 434,435,466 639,640 068 668 056, 057, 421 009, 163, 484, 489, 633, 639, 640 026, 030, 531, 540, 543 25 1 123 255 128, 234, 590 053 224 472 312 022 155 043 421 254 632 377,609 088, 110, 315 592 491 329, 663 084, 406, 442, 664, 666 682 316 696 237,571
742
Johansson, K. Johns, M.K. Johnson, C.N. Johnson, D.R. Johnson, J.N. Johnson, P.D. Johnson, T.A. Johnston, D. -)I]. J.N, Johnstone, S. JoksoviC, M.D. Jolicoeur, E. Jona, H. Jonasson, C. Jones Jr. J, Jones, A.B. Jones, A.D. JQLKLL
.!sn&x
Jones, P.G. Jones, R.V.H. Jones. S. Jonsson, S.Y. Joo, Y.11. Jordan, R.W. Jorge, Z.D.
JBrgensen, M. Jose, B. Joshi. N.N. Joshi, P.L. Jothilingam, S Journet, M. Jouvrnaux. Y, Joya, T . Ju, Y. Juaristi, E. Judd, D.B. JueC. s. Jucrtas, I.
.bu.GL
AIJTHOR INDEX
460 054 670 267 620 512 652 233 522 299 015, 361 57 1 058 212 07 1 537 210 165 574 064, 450 380 245, 269 43 1 218, 234 059 500,503 689 364 435 495 025, 197, 202, 531, 540, 565, 570, 571, 5x0, 597, 600, 697, 699, 701 289 423 197 414 164 594 425 068 3x7 035, 369, 468 515 257 473 295 104
Juhl, K. Julienne, K. hC.-E Jun, Y.M. Junckers, T.H.M. Jung, H.H. Jung, 1 . X
JlmLuL Jung, J.-C. Jung, J.-H.
.hlLKx
Jung, Jung, Jung, Jung,
L.-j. M.E. S.11.
Y.-J.
JlulLxx Jurkauskas, V Juroki. Y. Jurono, N.
Lvothi. T&
JCahalka. G.W.
Kahlaoui, N.M. XahoudiaB Knbuto, C. Kadnikov, D.V. Kadokawa. J.-1. b d o t a , I. Kadota, K. Kadoya, R. Kadyrov, R. Kaean. H.B, Kagayama, A.
540, 600, 339,342 393,396 261, 277 291 432 366 135 372, 627 553, 707 222, 234, 247, 279, 306, 316, 698 657 623 006, 116, 063, 277, 627,381 587 162, 564 261 532 152 305
697
246, 286, 338,
459 372,
003, 006, 015, 020, 035, 036, 151, 156, 270, 368, 369, 388, 468, 483, 487, 488, 601, 662, 695 437 477, 700, 701, 704 694 095, 399, 686 637 3 17 173, 619, 652 087 455 158 549 504, 505, 547
AUTHOR INDEX
Kageyama, H. Kagoshuna, II. Kaieda, A. Kainz, S. Kajikawa, S. Kajimoto, II. Kajiro, €1. Kakehi, A. Kakiuchi, F. Kakiuchi, N. Kakiya, €1. Kaku, H. Kakuda, A. Kakumoto, K. Kakusawa, N. Kakushou, F. Kakuuchi, A. Kalantari, F.
KJILSSL. . ,... M,
Kalita, B. Kalita, D. Kalsey, S. Kalvinsh, I. Kaly an akuniar, R . Kalz, W. Xainal. A. Kamat, S.K. Kainat, V.P. Kamata, T. Kainatani, A. Kamhle, R.M. Kamhle, V.T. Kame, T. Kameda, K. Kameda, M. Kainei, T. Kamer, P.C.J. Kainetani, A. Kainetani, Y. Karneyama, 1-1. ~a11l~ya11~a, rr.
029, 537, 539, 607 235, 278, 286, 569, 608, 611 278 230 284 077 022, 303 132 339 089, 193 622 274,379, 404 538 091, 094, 315, 409 036, 146, 468 656 074 198, 329 492 154 605, 673 084 033 011, 471, 696 665 209,463 316 447 575 085, 099, 106, 111, 301 415 183, 528 284 189 425,428, 536 068, 140 043,078 27 1 506 598 142 064, 067, 105, 293 577 0115 339 223
Kamijo, S. Kamikawa, K. KamiAski, R. Kamitani, A. Kruniura, K. Kainiya, M. Kan, Y. Kanahe, 0. Kanagasahapathy, S. Kanai, K. Kanai, M. Kanayama, T . Kanazawa, S. G n d a , T. Kaneko, T. Kaneko, Y. Kanematsu, T. Kanemoto, S. Kanetaka, S . Kanetani, F. J(anc. H.-Y, Xang. J, Kang, K.H. Kang, L. Kang, S . Kang, S.-I-I.
Kang, S.B. Kang, T. Kang, Y. Kanie, K. Kannan, V. Kano, T . Kano,T. Kantha, J.V.B. Kao, J. Kaptein, B . Karaev, S.F. Karami, B. Karasu, M.
743
393, 609, 616 061 153 622 257 249, 672 020 044 421 49 1 312,356 522 071, 533, 647, 648 595 340 160 096, 110,362 629, 636 336 273 533 684 644 409 031, 126 304 492, 690 003, 682 135 001, 002, 222, 223, 224, 225, 281, 399, 411, 550, 553, 577, 584,661 003, 382,682 348 301 369 553 124 283 304, 346, 383, 479,521, 704 07 1 641 276, 565 472 643 166, 609 317
744
Kwchaudhuri, N. Kudile, G.B. Kardon, F. Karimi, A.-R.
. .
ariini. B.
Kuimi, M.11. Karlstriim, A.S.E. Karstens, W.F.J. Kasano, A. Kasatkin, A.N. Kasei, A. Kashihara, K. Kashiwagi, R . Xass. S.R. Kasthuraiah, M. Kasture, S.P. Kasuga, Y. Katagiri, N. Katampe, I. Kataoka, K. Kataoka, M. Kataoka, 0. Katayama, K. Kate, S . S . Kato, F. Kato, H.
K&x
Kato, M. Kato. N.
Kate. s.
Kato. Y. Katohgi, h4.
I
Katsumata. A. Kauch, M. Kaufinan, M.D. Kaufinan, T.S. Kaur, G . Kaur, J. Kaur, K.P.
AIJTHORINDEX
413, 500, 639 020 615 399 102, 108, 111, 112, 113, 114, 315, 364 078 130, 461 311 586, 591 086 690 518 126 126 329 23 1 078, 143, 471 297 152 332 022 056 413 433 472 190 299 653 562 447 511, 671 367,462, 615 235, 239 047, 170, 240, 252, 265, 279, 317, 407, 413, 467, 580, 694 052, 092, 126, 213, 214, 217, 218, 219, 329, 352, 354, 475, 527, 566 183 043 618 578 418 095 686
Kauss, v. Kavita, B. Kawabata, €1. Kawabata, T. Kawachi, Y. Kawada, A. Kawafuchi, H. Kawagishi, S. Kawaliana, R. Kawahma, F. Kawai, H. Kawai, M .
hUiL
Kawllkami, M. Kawakaini, Y. Kawamura, M. Kawanura, T. Kawma, A. Kawat& Kawanishi, T. Kawano, T. Kawasaki, M. Kawasaki, T. Kawasaki, Y. Kawashima, J. Kawata, K. Kawatsura, M. J(awecki. R. Kayaki, Y. bye. p.'L Kazankova, M.A. Kazantsev, A.V. Kazemi, F. Keane, J.M. Kee, M. Keenan, M. Keith, J.M. Keitoku, T. Kel'in, A. Kelley, S. Kellner, A. e l l o ~ c .R.M. Kemp, M.I. Kendall, C. Kennedy, A.R. Kennedy, D.J.
316 704 079 110 539 404 290 654 069,523 622 341 032, 506 062, 157, 158 611 387, 437, 459 558,573 406,435 OW 023, 036, 563 245 398 547 115 630 002, 150, 185 177 408 605 328,521 658 330 429 689 048 572 626 037, 065, 337, 507, 640 705 512 309,542 391 611 669 388 43 1 276,565 635 470 178,303, 617 154
AUTHOR INDEX
Kennedy, LJ. Kermane, E.-M. Kerbal, A. Kernag, C.A. Kerr, M.A. Keirigan, N.J. Kerschner, J. Kerwedo, S. Kesavan, V. Kesselgruher, M. Kesynkin, D.V. Keum, G . Keum, S.-K. Keypour, 11. Keyvan, A. Kczuka, S . JChadilkar. B.M, Khakshoor, 0.
Khan, A.A. Khan. AT. Khan, F.
J C h m
Khan, K.M. Khan, N.II. Khasnohis, S . Khau, V.V.
Khmel'nitskaya, I3.A. Khoee, s. Khosropour, A.K. Khrustalev, V.N. Khurnna, A.
Khurana. J.M. Kiakojoori, R. Kiakoojori. R.
Kiany-Borazjmi, M. Kinsat, A . R . Kido, Y. Kiely, A.F. Kiewel, K. Kiguchi, T.
321 08 1 356 096 302, 560 092, 316, 635, 680, 684, 685 349 359 654 517, 697 02 1 371 003, 382, 682 007, 400,451 473 230 552 257, 287, 401, 547, 614, 413 278 077, 083 255 108, 109, 665 092 037, 412, 480 275 350, 351 248 521 415 120 093,230, 260 096, 411 315, 415 649 399 063, 447 098 097 111, 168, 282, 473 110, 305 234 634 292 454 482 586 518
745
Kihara, N. Kii, S . Kikuchi, D. Kikuchi, K. Kikuchi, S.4. Kikuchi, T. Kikuchi, W. Klkutawa. Y, Kikukawa, T. a w r n . J.D. Kim, A.R.
B.S. B.T. D.-€-I. D.J. D.W. Kin. D.Y. Kim, II. Kim, Kim, Kim, Kim, Kim,
Kim, Kim, Kim, Kim, Kim, Kim, Kim,
Kim, Kim. Kim, Kim, Kim, Kim, Kim,
11.-C.
1I.-J. €I.&
K-Y. H.J. H.R. H.S.
I1.Y. J. J.-11. J.-W. J.D. J.II.
J.M.
Kim. J.S. Kim, J.Y. Kim, K.-i. Kim, K.-J.
a n . K.S. Kim, M.-S.
Kim, M.J. Kim, M.K. &m. S .
Kim, S.-G. Kim, S.-11. Kim, s.4.
049, 326 022 643 06 1 298 407 079, 141 268, 277, 515 565 191 5 15 261, 277 308,351, 671 170, 244 052, 167, 406 223 055 670 195, 260, 703 596 686 221,350, 571 606 010,621 595 25 1 260, 277, 555, 613 03 1 009, 229 007, 451 222 587 03 1, 275, 400 090 165, 613 170, 277, 432, 687 043, 209 189 577,584 186, 382, 544 223, 553 2fi 043 067, 124, 220, 339, 444, 477, 492, 651 195, 219 049 316,338
AUTIIOR INDEX
746
Kitn, S.-K. Kim, S.-W. Kim, S.C. S.H,
Kim, S.K. Kim, S.M. Kim, T.-J. Kim, T.Y KhLL
K h , Y.-H. Kim, Kitn, Kim, Kim, Kim. Kim.
&.
Y.-M. Y.K. Y.M. Y.S. J. J.11. J.N,
Kim. M.-J. Kimachi, T. Kimura, C. Kimura, K. Kimura, M. Kimura, T. Kimura, Y. Kinchin, E. Kindelinan, S.S. King, S.A. Kinome, Y. Kinoshita, A. Kircher, G. Kirihata, M. Kirk, G.G.
Kisanga, P. Kisanga, P.B. JCise. N . Kishi, A. Kishikawa, Y. Kishimoto. S .
147 351, 676, 679 353, 358 400, 434, 449, 513, 525, 551, 565, 574, 575, 576, 668 209 195 515 052, 167, 170, 275, 277, 406 555 003, 132, 301, 304, 382, 682 396, 444, 525, 557, 627, 697 002 274 161 200 379 668 555 260 024 406 524 033, 037, 041, 406, 505, 556, 563 097, 193 295,346 552 453,515 210 364 120 469 392, 416 171 250 684 140, 269 342,441, 549 698 388, 569, 571, 592, 635 409, 623 164 038
Kishimoto, Y.
KkLL KhX. Kita, Y.
Kitagaki, S. Kitagawa, II. Kitagawa, K. Kitagawa, 0. Kitagwa, H. Kitaichi, Y. Kitamua, T. Kitamura. M. Kitamura, T. Kitano, K. Kitano, Y. Kitoh, K. Kitov, P.I. Kiyosawa, Y. Kizaki, N. Kizil, M. Klajn, R. IQiiRL
Klapars, A. Klaps, E. Klein, H. Klepacz, A. Klimkina, E.V. Kloc, K. Klomp, D. Klotz, P. Klumpp. D.A. Iyunivasu. H. Knapp, F.H. Knausz, D. Knettle, B.W. KnicTht. D.W. b i e h t . J.G, Knochel. P.
401 016 348 082, 355, 398, 476, 595, 644, 660, 667 623 093,373, 684 049, 144 182, 437,666 093 357,391 592 207, 499, 612 011, 014, 433, 434, 435, 466, 478,582 062 124, 220, 338, 339 607 078 141, 147, 191 076 056 568 362 648 292 246, 254, 272 438 104 230, 265, 603 270, 283 01 1 586 238, 611 183 536 148 6 15 276 574 638 071, 095, 137, 139, 147, 149, 150, 182, 347, 362, 422, 487, 600, 690 031
AUTHOR INDEX
Knopff, 0. Know, K.R. Knudsen, K.R. Knutson, C.E. KO, B.-S. KO, J.-J.
KO. K.-Y, KQA
Koada, S. Kohayashi, Kohayashi, Kohayashi, Kohavashi..
F. K. M.
. S.
Kohayashi, Sh. Kohayashi, T. Kobayashi, Y. Kohelkova, N.M. Kobori, K. Koch, D. Koch, R. Kochetkov, A N . K&var, M. KoZvskf, P. Kodarna, H. Kodama, T. Koehler, K. Koenig, R.J. Koh. 1I.Y. Koh, J.11. KGhler, K. Kiihler, V. Kohmura, Y
K!&di
Koike, T. Koizumi, N . Koizuini. T. Kojima, K. Kojima, M . Kojuna, S.
300 216 699, 701 640 044, 397, 550 007, 451, 668 113 705 368 538 079, 515, 631 099 018, 047, 154, 198, 273, 277, 284, 329, 404, 500, 520, 522, 534, 539, 543, 544, 545, 546, 558, 573, 606, 607, 609, 612, 662 288 182 031. 079, 131, 444, 706 612 063 456 209 429 3 20 129 128, 88 013, 049, 093, 388 664 452 642 132, 301, 304, 554 55 1 466 628 329 172 542, 645 316 476, 500 094, 412 58 1 583
Kojima, T. Kokurnai, R. Kolagar, S. Kolis, S.P. Kollhr, L. &He. t J * Kollner, C. Kolomiets, A.F. Koltun, E.S. Komatsu, II. Komatsu. M. Komatsuhara, N. Komine, N. Komiyama, S. Komori, S. Komoto, I. Konda,Y. Kondo, J. Kondo, K. Kondo, M. Kondo, S. Kondo, S.-i.
ibldLL
IkuxkLx
Kondratenko, M.A. Kong, N. Kiinig, W.A. Konishi, 11. Konishi, T. Xonno. T, pononelski. J.P. KonstantinoviC, S.K. Konuma, M. Xonwar. D, Kopp, F. Koppen, I. Koradin, C. Kordes, M. Koretsune, R. Korolev, D.N. Koroniak, L. Korotchenko, N. Koseki, Y. Koshiha, N. Koshino, II. Koshoji, G. Kossir, A.
747
121, 131, 149, 579 553 078 2x1 208 096 527 612 329 495 259,327, 361 210, 562 345, 559, 329, 3x4 559 609 173 539 248 400 249 182 227 062 002, 288, 344, 681 518 462 456 149 515 032 430 070, 155 058 475 299, 442 182 5x7 690 573 450 389 075 665 006 346 629 184 674
748
AUTHOR INDEX
Koster, P. Kotani, K. Kotha, S.
Jhhx.LL Kotsuki. Ii, Koulotakis, N.P. Kouno, R. Kousaka, T. Kovac, F. Kowal, J.J. Kowalchick, J.E. Koyashu, K. Kozima, S. Kracke, B.
Krafczyk, R. Kraskik, P.E. a a u s . G.k w s e .
N.
Krauss, 1.1. Kreethaduimongdat, T. Kreimerinan, S. Krernzow, D. IG-euder, R. Kreutz, O.C. fiw,einuhski, M.P. & J Q Krishnaswamy, D. KWpp. P.J. Krueger, C.A. Krzeminski, M.P. Krzemisnski, M.P. Ku, C.-K. Kuang, C . Kuang, Q,-Q. Kuhlitski, V.S. Kuho, M. Kubota, A. Kuhota, K.-i. Kubota, T.
484 177 339 467 119, 426, 483, 693 121, 131, 149, 296, 331, 332 556 279 707 184 393 425 626 001 535 122 238, 505 673 489 129, 680 600 394, 450, 628 211, 431, 438, 651, 656 103 17Y 327 617 44 1 058 556 501 221, 536 080,553 228 282, 362 610 647 319 122 367,447 504 600 626 3 73 561 502 690
Kuhlman, M.L. Kula, M.-R. Kulak, A.N. -vich. O.G. Kulkam, S.R. Kulkarni, G.M. Kulkarni, V. Kumagai, N. Kurnar, D. Kumar, G.D.K. Kumar, G.M. Kumar. II.M.S, Kumar, J.S.D. Kumar, K.A. Kumar, K.K. Kumar, S.K. Kumar, V.S. Kumaraguruharan, N. Kuinareswaran, R. Kumps, L. Kunai. A. Bundu. N.G, Kung, D.W.
Kuntz, K.W. Kunwar, A.C.
KUO,J.-H. Kuraishi, M.
Kurchan, A.N. Kurihayashi, M. Kurihara. M.
Kurita. J,
Kuriyama, M. Kurohoshi, M. Kuroda, M. Kuroki, Y. Kurono, N. Kurosawa, K. Kuroyanagi, M.
508 05 1 486 661 120, 646, 669 112 585 084,373 179 502,535 409 249 255, 524,573 047, 082, 209, 280, 301, 303, 418,499 304 231, 248, 608 419 314,362 601 524 180, 631 081, 327 450 641, 644 493 246 063 380,486 251, 428 610 601 3 14 524 347 350,351 002,645 079, 668 492 195 038, 369 693 414 03 1 138 136, 251, 536, 538 132 697
AUTHOR INDEX
Kurushiina, 11. Kurusu, Y. Kurz, T. Kusnka, C. Kusaki, I. Kusama, 14. Kusui, K. Kutateladze. A.G. Kuwahara, T. Kuwahe, S.4. Kuwano, K. Kvi&la, J. Kwan, M.1,. Kwast, A. Kwok, W.H. Kwon, D.W. KwoI1, H.-S. Kwon, J.S. Kwon, 0 . 0 . Kwon, S . Kwon, S.Y. moll.
*r.w.
Kwong, F.Y. Kwone. I-I.-L. Kyoda, M. Kyoumura, K. Kyte, B.
La Paih, J. La, D.S.
j,aali. K.K.
Lahiizi, G. Lahrosse, J.-R. Lacroix, T. u \ 1 e r t a . P. Lai, C.W. Lai. G . Lai, J.-Y. Lai, S. Laicher, F. Lake, F. Lakhvich, F.A. Labhminmayann, V. LaliC, G.
20 1 034,040 407 380 3 14 427 044 098, 347 384 336 058 3 70 44 1 648 157 627 223 132 090 246 090 161, 498 292 031, 328 703 688 330
312 634 465 050, 403, 478 165 650, 657 082 212 292 417 338 519 407 024 383 230, 242, 326, 356, 413, 476 107, 308 538, 541
Lam, H.W. P.Y.S. Larn , W .W .-L. Lam, Y.-F. Lamar, J.E. Lanbert, A. Lamhert, D. Liuiirani, M. Landini, D. Lando, V.R. Lang, F. Langemann, K.
l2usLE Langford, M.M. Langille, J.D. Langille, N.F. Langkopf, E.
Lannon, M.I. Lannuml, M. Lmz, M. Lanz, MM. Lapinsky, D.J. Laporterie, A. Large, J.M. Largeron, M. Larhed, M.
Larichev, V.S. Larina, L.I. Larksup, C.
Larsen, A.O. Larsen, R.D. Laskar, D.D. Lasne, M.-C. Laso, N.M. Latiri, 2.
Lau, K.-C. Lau, T.-C. Lauenstein, 0.
749
436 242 154 536 413 331 395 227 064 151, 253 134 290 467 247 456 212, 451, 628, 655, 673 480 302 664 465 643 613 227 270 270 183 478 243 307 399, 460, 610, 6 17 649 598 253, 600 115, 116, 118, 164, 173, 285, 401, 426, 430, 435, 610, 636, 637, 639, 683 551 259, 425 108, 114, 301, 302,471 261 705 619 359, 475, 525 668 404 371, 374
AUTHOR INDEX
750
Laurent, M. Laurenti, D. hret. C Laureyn, I. Lauria, E. Lautens. M. Laux, M. Lavanya, B. Lavijani, €1. Lavis, J.M. Lavoisier-Gallo, T. Lawson, E.C. Laxman, E. Laxman, N. Laxmi, Y.R.S. Layek, S. Lazny, R.
Le Beire, N. Le Bideau. F, IR Blanc, R. Le Blond, C.R.
Le Boisselier, V. Le Drian, C. Le Fol, R. Le Gall, E. Le G u s , P. Le Guyader, F. Le IIuCrou, Y. Le Paih, J. Lea, L. Leach, A.G. Leach, J.D. Leahy, D.K. Leanna, M.R. LeBlond, C. Lehreton, C. Leconte, S. Lectka. T. Lecubin, I;. Ledger, J.A. h e . A.S.-Y. Lee, B.M. Lee, B.S. Lee, C.-II. Lee, c . - w . Lee, C.B.
265 288 647 585 66 1 400, 446, 452, 526, 555,557 656 080 609 435 677 065 085, 111, 301 367 530 357, 366 396 457 315 079 293 134 013 144 326 129 369 184 069 434, 639, 660 126 237 173,345 147, 152 344 019 060
280 669 246, 256, 262A 624 148 247 041, 077, 085, 311, 409 26 1 692, 704 554, 642 186,704,707 620
Lee, ‘2.11. Lee, C.W.
Lee, D. Lee, D.-S. Lee, D.-Y.
m Lee, D.Y. m Lee, F.-C. Lee, €1.
Lee, H.F. Lee, H.J. Lee, H.M.
u Lee, J.G. Lee, J.H. Lee, J.T.
J&eJJX
w
Lee, K.-D. Lee, K.-J. Lee, K.I. Lee, K.Y. Lee, M. Lee, M.H. Lee, M.J. Lee, N.R.
I&dLH% Lee. S. Lee. S.-G. Lee, S.-H. Lee, S.-J. Lee, S.-k. Lee, s . - w .
Lee, s.-Y. Lee. S.H. Lee, S.I. Lee, S.i. Lee, S.J.
136 620, 632 28 1 061, 200 393 403 090 209,554 675 366,396 213 613 555 145, 177,351 014, 044, 329, 627, 663 301 126 325 707 038, 067, 135, 203, 260, 410, 444, 554, 651, 686 596 353, 358, 366, 670 398 165, 555,613 094, 447 587 406 398 006, 038, 067, 135, 203, 554, 651, 686 232, 289, 292, 321 043, 681, 684 001, 223, 281 007, 451, 559 595 222, 223, 224, 553 625 031, 063, 118, 296, 305, 381, 599 679 678 668
AUTHOR INDEX
Lee, S.S. Lee, S.Y. Lee, w . 4 . Lee. w.K, Lee, W.S. Lee, Y. Lee, Y.-H. Lee, Y.-M. Lee, Y.-T. Lee, Y.C. L&Ll&
Lee-Ruff, E. Leese, M.P. Lefehvre, LM. Lefebvre, 0. Legrand, 0. Legros. J. Lehmann, C.W. Lei, X . 4 . -ton. J.L. Leijonmarck, H. Leitner, A.
676 704 031, 328 136, 265, 596 228 513 213 498 224 014 073, 170, 244 215 466 635 532 072 058, 531 358
LBvai, A. Levillain, J. Levy, O.B. Lewis, N. Lewis, T.
Lev. S.V.
092, 237, 621,
xdawLuL
Leroy, B. Lescop, c .
Li, C.-L. Li, D.-R.
LiG, Li, €I. Li. J.
400
489 324 103 697 136 284,456 059, 060, 061, 140, 143, 184, 249, 283 29 1 523 261 653 155 212 498 280 43 1 217 286 339 540, 688 112, 316, 557 499 149 060 127 514 365 464
Lemiitre, G.L.F. Lemillwau, C. Lemoucheux, L. Lenardiio, E.J. Lenges, C.P. Lenoir, I. Lensen, N. Uon, H. L o u , s.-P. Lerario, V.L. Lerchner, A. Leiiverend, C.
Lhermitte, F. Lhoste, P. Li, C. Li, C.-H. Li. C.-J,
LdLL LiJL Li, Li, Li, Li,
L. L.-H. 1.-J. N.-S.
LiE LiB. Li, T.
Li.T.-S, Li, T.-W. Li, W. Li, W.-K. Li, W.-S. Li, X. Li, Li, Li, Li, Li,
X.-G. X.-R.
X.-Y. Y. Y.-C.
LiJLL Liz.
J4LzL
Lian, H. Liang, C.-G. Liang, F.
751
629 362 650, 657 213 314 039, 144, 150, 202, 203, 204, 337, 342, 527, 598, 642, 643, 644, 663 326 668 009,434, 449, 551, 554, 559, 565, 574, 575, 576, 680 595 009, 010, 163, 277, 337, 484, 489, 633, 639,, 640, 643 442 530 635, 667 024,038, 507 442 015,487 196,451, 491 294 226,507 088, 110, 315, 442 314 159, 166, 191 668 252 062, 200, 485, 668 023 546 640 028,315 3 14 312 050, 051, 068, 155, 217, 269, 286, 373, 487 055 193 655,705 599
752
Liao, B. Lim, W. Liao, Y.-C. Lihertini, E. Lieh. F, beheskind. L.S, Liehl, M. ma.A.1, Liepins, V. Liesen, P.1. Liiu, G.-B. Liiu, Y. Likhotvurik, I.T. Lill, S.O.N. Lim, C.J. Lim, D.S. Lim, s. Lirn, J.S. Lim. S.-G. Lim, Y.M. Limhurg, D.C. Lin, C.-C. Lin, C.-F. 1,in. G.-0. Lin, G.-q. Lin, H.-H. Lin, L.-S. Lin, L.C. Lin, P.-Y. Lin, S.-I. J i n . W. Lin, X . Lin, Y.-M. Lin. Y . 3 . Lin. J.-S. Linder, M.R. Lindsay, C.I. Lindsay, D.M.
J,indstriim. IT .M. LinP Y.-C, Linstrumelle, G. Liotta, C.L. Liotta, L.F. J ipifixka. T. J.ipshutz. B J f .
AUTHOR INDEX
638 539 085 561, 585 635 134, 256, 397, 398, 638 456 256 175, 453, 461 463 160 448 274 553 477 269 209 358 396 116 013 158 43 1 055, 324, 330 137 675 409 536 166, 241 244 708 240, 603 057 298, 566 314 259 152, 575 092, 680, 684, 685 238,517 163,594 494 191 430, 437 287 006, 027, 053, 146, 147, 148, 292, 309,381, 542 169
List.
B.
Liu, A. Liu, B. Liu, Liu, Liu, Liu, Liu, Liu, Liu,
C.-C. C.-J. D.
D.-X. D.-x.
G.-H. 11.
Liu, 5. Liu, J.-P. Liu, J.-T. Liu, J.-X. Liu, J.-Y. Liu. L.T. Liu, M. Liu, Q. Liu, R.S.H. Liu, S. Liu, S.-Y. Liu, W.-y. L l U A
Liu, Y.
Lium. Y.
. .
Llvlnphouse. T. Livingston, R.C. Liz, R. Lizos, D. Liirzani-Cuvelier,L. Llebaria, A. Lloyd, C.T. LO, M.M.-C. Lo, P.C.-K. Lobo, A.M. Locher, C. Lockley, W.J.S. Lodder, G. Loenard. N.M.
121, 197, 501, 534, 540, 688 002, 145, 449, 456,464 107 043, 234, 305, 641 314 3 14 505 022 023 025 053 048, 156, 673 060, 507 106 221,222,441 121 222 064, 612 107 247,528, 664 326 122 243 141,510 020,311 053, 179, 411 143, 334, 385, 483, 537, 592, 706 254, 387, 492, 690 254 595 274, 460,582 484 056 178 654 101 032 094 643 687 569 286 380 665 100
AUTHOR INDEX
Loenakv. R . N , Loft, M.S. T.-P.
Loiseau, M. Lokot, I.P. Lomhardi, J. S. London, G. Longmire, J.M. Lones. C.C. Lopes, C.S.J. Lopes, R.S.C.
Lopez, L. Lopez, M. IApez, F. Ikpez, L.A. Ldpez, R . Ldpez, s. Mpez-CortCs, J.G. Ldpez-Gonzlilez, D. Lopusinski, A. Lotoski, J.A. Loudwig, S. I-ough, A.J. Louie, J. b4U-A b v e . B .E. Love, I. Love, J.A. 1.ovely. C..I, LOW,K.-I-I. Lowden, T.R. Lu, G.
u
IA, J.-I;. Lu, K. Lu, P.
LLs.
Lu, s.-Y. w.
LU,
275 130 605 026, 028, 029, 036, 040, 175, 249, 336, 341, 521, 522, 538, 545, 546 151 654 383 325 027,519 384 590 410 301 410 303 185, 206, 217, 458 060 486 119 338 218 685 472 473 699 122 076 037, 558 456 263, 287, 393, 498, 704 307, 392 087 465 254, 675 001 596 485 166, 252 027 180, 571 449 123, 244, 250 380 240, 324, 434,
753
Lu, Y. Lu, Y.-Y. Lii, s. Lii, S.-M. Lii, w. Lii, Y.-x. Lubin-Germain, N. Lucking, U. Luedtke, N.W. LUerS,
s.
Luis, A.L.
Lukashev. N.V, Lukasiewicz, M. Luliriski, P. Lunot, S.A.
hLE&
Luo, M. Luo, M.-M. Lusch, R.K. Lusinchi, X. Lutete, L.M. Lutsenko, S. Ly, T.W. Lydon, K.M. Lye, P.-L.
LYiaJJL l.fYwJL
Lynch, V.
Ma. Ma, Ma, Ma, Ma, Ma,
D. 1-1. €1.-r. J. J.-A. L.-T.
MLs'
Ma, Y. Ma, Y.-R.
435, 466, 556, 582 434, 474, 588, 631 010 229 530 056 214 418 042, 463 489 247 459 221, 536 0s 1 689 010 019 373,374 694 172 040, 559 056 436 260 619, 652 056 698 673 341, 654 249 343 355, 596, 645 540
404 252 152 556 215 336 494, 634, 635, 639,656, 667 348,517 110, 315
754
AUTHOR INDEX
Ma.Y.-X. Ma, Z.
Macchitella, D. Macdonald, G. Mace, LJI. MacGee. D.L Machida, M. Machino, C. Machrouchi, F. Machrouhi, F. Mackintosh, N. D.W.C. MacNeil, S.L. Macqururie, D.J. Madalengoitia, J.S. Madan, C. Madan, Ch. Madec, J. Madhur, Ch. Madhuri,C.R. Madhuri, Ch. Madhushaw, R.J. Madhusudhan, P. Madine, J.W. Madrakian, E. Madnisz, .I. Madyar, V.R. Maeda, T. Maeda, Y. Maed4Y. Maegawa, T. Maekawa, H. Maekawa, N. Maema, R. Maes, B.U.W. Maesano, M.G. Maestro, M A . Maeyama, K. Maffei. M. Maftouh, M. Magdolen, P. .
I
I.
Magee, M.P.
020, 3 11 155 214, 425 092 365 160 445 173 428, 536 529 517 26 1 194, 561, 568, 572, 584, 644 232 250, 371 33 1 217 255 417, 700 203 054 378 130 275 601 326 313, 418 432 473, 477, 479 104 547 562 437 091, 094 390 476 082, 339, 491, 595, 626, 660, 703 244 306 29 1 332 127, 684 099, 427 055 275 29 1 173, 345 271
Mzgerlein, W Magnin-Lachaux, M. Magnus, A S . JgggIlUS.
P,
Mague, J.T. Mah, Y.J. Mahale, G.D. Mahalingam, A.K. Mahata, P.K. Mahhouhghah, N. Mahdavi, H. Mahesh, B. Mahia, J. Mahmood, S.J. Mahmud, H. Mahon, M.F.
Mahrwald.R.
Maietti, S. MaiIlard, D. Mailleux, I. Main, A.D. Maiti, A. Maiti, G. Maiti, S. Maiuolo, L. Majee, A. Majo, V.J. Majtahedi, M.M. Majumdar, K.K. Mak, C.-K.
MAuA
Maki, T. Makino, H. Makino, K. Makioka, Y. Makiuchi, N. Makone, S.S. Makosza, M. Makwana, V.D. Malan, C.
- M,
,
Malda, H.
Maleev, V.I.
327 110, 416, 609, 615, 635, 706 5G8 095 063, 193, 540, 548 642 5 15 423 075, 080, 083, 087
564
414 046 306 127, 684 628 254 130 288, 490, 541, 547 351 059, 128 335 285 078, 440 366, 371, 642 183 370 085 673 112 576 404 159 065,081, 273 300, 676 514 592,702 390 111,112 618 093 041, 236, 326 058, 126 652 452 049, 389, 427, 435 600
AUTHOR INDEX
Malkov, A.V. Malladi, R.R.
Malnick, L.M. Malusare, M.G. Mamai, A. Marndani, I1.T. Mamposo, T. Man, M.W.C. Manahe, K. Managan, T. Mafias, R. Mancheiio, 0.G Mancini, G. Mantlal, B. Mandal, G . C . Mandal, M. Mandoli, A. Mane, K.B. Mang, J.Y. Mangeney, P. Manhas, M.S. Manke, D.R. Mann, L.W. Mannarini, N. Mannina, L. Mannucci, S. Mano, E. Mano, M Manohu, B. Manoso, A S . Mansoor, 1J.P. Manta, N. p&jy. J:I, Mao, J.
March, S. Marchueta, I. Mmcotte, F.-A. Marcotullio. M.C.
129 015,020,388 019, 092, 095, 096, 099, 106, 41 1 376 084 217 39 1 499 055 154, 198, 329, 534, 544, 607, 612 580 527 024 090 123 357,366 574 196, 199 371 260 181, 196, 557 161 708 238, 400, 611 458 185 636 652 010 515 325 133 636 519 166 594 368 068, 210, 370, 503, 504, 506, 604, 681 195 265 118, 386 163 083, 085, 088, 109, 516, 575, 649
&larcoux. J.-F.
MaalLL
MiuxLL
Marie, J.-X. Mariinez, R. Marin, M. Marinelli, Marinelli, F. Marinez, E.R. Marini, F. Marino-Gonzhlez, A. Marion, F.
Miirk6, L. Markworth, C.J. MarmsPter, F.P. Maroulis. A.J. Marques, A. Marques, F. de.A.
IkikuaL
Mkquez, F. MarquiB, J. Marra, C. Marsault, D. Marshall, D.R. Marshall. J.A. Marshall, W.J. Martel, J. Martelli, G. Martens. J. Martin, A. Martin, C.G. Martin, E. Martin, H.J. Martin. S.F. Martin. V.S. Martin, M. Martin, S.E. Martin-Matute, B. Martin-Kuiz, B.
755
163, 164, 219, 273,302 548 137, 190, 614 294 220, 221, 657 667 312 474 616 137, 165, 208, 616, 640, 655 480 622 390 326 250, 327 086, 097, 112, 316, 443, 450, 557 104 276, 284 085 178 279 474 069 295 032 478 336 467 404 028 489 024,057 216 248 056 401 178 127 197 211,440, 581 490 302 475 452 455 521
756
Martinez, I. Martinez, F. Martinez, I. Martinez, P. Martinez, S. Martins, T.L.C. Marto, S.J.L. Martorell, A.
Marx, A.
Mascarenhas, C.M. Masdeu-Bult6, A.M.
IldiwLL
Maskos, K. Mason, H.J. Massa, A. Massaccesi, M. Massera, C. Massicot, F. Masson, G. Mastracchio, A. Masuda. Y, Masuda, Y. Masuno, M.N. Mateo, C. Mathes, C. Mathew, T. Mathieu, J. Matos, M.R.P.N. Matovii., R.
Matsuda. I.
Matsuda, K.
A'CJTI-IORINDEX
66 1 145 101 618 185 119, 672 297 310,494, 632 569 197 021, 022, 251, 311, 318, 323, 337, 487, 543, 598 039 065, 117 013, 049, 093, 388, 506 510, 520 127 102, 367 648 269 37 1 355, 361, 475 068, 503 312, 495 587 139, 141, 382 471 127 280 140, 189 468 160 034, 040 09 1 164 489, 695 470 122 132 538, 541 363, 428, 446, 661, 663, 693 066 219, 564, 590, 633, 637, 679 434
Matsuda. T. Matsuei. M, Matsui, C. Matsui, R. Matsukawa, S. Matsumoto, K. Matsumoto. N. Matsumoto, S . Matsumoto, Y. Matsurnura, H. Matsumura, R. Matsumura, S. Matsumura. Y. Matsunaga, H. Matsunaga, S. Matsunaka, K. Matsuo, J . 4 . Matsuo, Y . Matsuoka, T. Matsushima, Y. Matsushita, A. Matsushita, T. Matsuzawa, H. Matsuzuno, M. Matty, L. Matui, C. Matusbara, T. Matusmoto, N. MauPhan. P.L Maulebn, P. Maw, G . Miximo, N. Maxwell, J.P. May, E.J. Mayasundari, A. Maycock, C.D. Mavoral. J.A. Mavr. €1. MawarEue. J, Mazidi, M.R. Mazzacani. A. Mamanti, G. McBride, C.M. McCarron, M. McCarthv. .I.& McClure. M.S.
058,497 267,355, 644 641 159 521 352,450, 644 544 041 029 426 528 390 065, 081, 273 063 200, 207, 502, 535 014, 051 079, 080, 093, 094, 099, 141, 373, 404, 684 537 121, 131 288 539 096 054 457 302 644 022 519
Xl
175 596 508 331 321 180 075 215, 674 153 685 105 110, 609, 615, 635, 706 556 282, 296, 648 172 015 189, 388 134
AUTIIOR INDEX
McCluskev. & McComhie. S.W. McCormac, P.B. McCullagh, J.V. McCusker, C.F. McCusker, J.E. McDonald. C.E, McGanigle, E.M. McGrail, P.T. McGrath, D.V. McKaeue. A.B. MeKendry, S . McKillop, A. McKinnell, R.M. McKoon, E. McLaughlin, M. McLaughlin, M.J. McLeod, D. Mc1,eod. M.D. McRiner, A.J. McSorley, E. Mealy, M.J. Mecca, T. Mechiom, P. Mecozzi, T. M&iarovd, M. Medici, A. Mehler, G. Mehlmunn, J.F. Mehltretter, G. Mehltretter, G.M. Mehta, B.K. Mehta, S. Mejer . G . B . Meier, T. Mekhtieva, V.Z. Melchioiw, P. Mella, M. Memarian. I1.R. Menchaca, R. Mtndez, M Mindez-Andino, J.
040 1x1, 244,322 466 120 522 285 626 276, 284 285 349 152, 575 096 500 316 340 095, 479 191 628 606 549 307 276, 617 134 081, 281 024 024 570 291, 384 351 158 048 254 390, 501 296 467 240 379 407 643 033, 647 375 379 630 111, 166, 168, 281, 282 237 432, 452, 460, 660, 691 464, 659
757
Meneses, R. Meneyrol, J. eneZe s.
P.IL
Meng, G. Meng, Q. Meng, Y . Mengel, W. Merchan, F. Mereiter, K. Mero, C.L. Meshram. I-I.M. Messina, F. Mestdagh, H. Mestres, R. Metsger, L.
MsLL
Meybodi, F.A. Mevers. A.L Meyers, C. JvIevers.A.1. Mezgueldi, B. Meziane, M.A.A. Mhehe, G . L .
u
Miao, H. Micalizio, G.C. Michaud, G.
Michelet, V. Michihata, T. Mickelson, E.T. Micklitsch, C.M. Micske. K Middlemiss, D. Mielniczak, G. MihailoviC, M.L. Mihara, J. Mihara, M. Mihovilovic, M.D. Mikalje, M.D. . . ikami. L Mikami, S . Mikeluk. M.D.
193, 381, 387, 541 275 363,494 418 028 203 623 262 028 262 148 088, 114, 305, 659 617 666 229 327 280, 622 188,209 339,342 332 084, 260 035 286 413 666 266 048 128 656 026,359 224 004,490 139, 453 044 473 626 060 316, 684 473 554 058 352 336, 341 330 473 034,521, 556 363 378
758
Miki, M. Miki, T. Mikoluk, M.D. Milan, D.S. Militzer, 1 I . C Millar, A. Millar, R.W. Miller. J.A. Miller. M.W. Miller, R.S. Miller, S.J. Miller, S.P. Milligan, G.L. Mills, C. Millward, D.B. . . Ilstein. D. Minaeifar, A. Minakata, S. Minami, T. Minamikawa, J.-i. Minari, M. Mineno, T.
M&&@?-
Mingo, P. Minisre, S.
MirlLr. Mino, T.
MirB, M.-A. Mirkhani, V. Mirza-Aghayan, M. Mirzaei, F. Mirzaei, M. Misnki, T. Mishahi, K. Mishirna, 11. Mishima, K. Mitamura, S. Mitani, J. Mitsudera, 11.
AUTHOR INDEX
036 207 160 230 390 134 479 306 156 181 508 364 520, 523 256 340 527 179, 455, 478 605 259, 327, 361 298, 607, 654, 707 267 146 076 095 638 582 092 025, 027, 125, 126, 127, 128, 129, 130 412 034, 037, 047, 072, 081, 108, 368, 532, 558, 65 1 40 1 280 075, 077, 109, 346, 475, 526 097 706 294 079, 312 356 682 065, 273 089, 404 555 413, 500, 639 622
Mitsudo, K. 0.
T.-&
Mitsui, K. Mitsui, T. Mitsuie, T. Mittal, M. Mitten, J.V. Miura, K.
Miura. T Miura, Y. Miwa, T. Miwa, Y. Miyabe, H. Miyagawa, C. Miyagi, M. Miyai, T. Miyaji, T. Miyake, K. Miyake, N. Miyake, Y. Miyano, S. Miyata, A. Miyata, N. Miyata, 0. Miyata, T. Miyata, Y. Miyatake, M. Miyazawa, E. Miyoshi, N. Mizohe, Y. Mizugaki, T. Mizuno, R. Mizuno, S. Mizuno, T. Mlochowski, J. Mlossteli. G, Jvfohcrc. C , Mochizuki, M. Moffett, K.K. Mogrenn, T. Mohaierani.
27 1 288, 344, 681 642 190 036 077 048 204, 239, 267, 506, 626 035, 054, 121, 184, 221 220, 298, 318, 518 284 502 590,619 268, 597,598 634 501 377,384 325 295 455 128 486, 684 135 046, 100 092 668 295 336 660 066 036, 144, 194, 203, 209, 240 515 038 300 110 344 031 661 011,015, 016 349 024,056, 127 038 465, 641 252 206, 278, 478 26 1 100
AUTHOR INDEX
Mohamed, M. Mohamnadi, M.
Mohan, (3.11.
& R.S. Mohanazadeh, F. Mohanta, P.K. Mohar, B. Mohile, S.S. Mohsenzadeh, F. Moilliet, J.S. Moineau, J. MojsiloviC Mojtahedi, M.M. Molander. C1.A. Molinaro, C.
.
.
Moll, G. Molvinger, K. Momeni, A.R. Momose, T. Monda, A. Mondal, E. Mondal, S. Mondon, M. Monfared. 11.11~ Moilflier. E. Mongin, F. Monnier-Benoit, N. Monopoli, A. M(>lltchanlo.J.-L Monteiro, A.Jd. Monteiro. N.
088, 233 206 075, 078, 080, 098, 101, 105, 107, 109, 111, 166, 168. 281, 282, 315, 411, 415, 526 044, 084, 101 078, 100, 108, 110, 392, 410 108 162, 285, 319, 399 372 315 257 374 464 058 089, 093, 102, 257, 268, 593 069, 070, 072, 134, 438, 527, 529 181 160 535, 704 060 166 416 693 108, 109 395 183 358 082 139 581 458 480, 481 134, 143, 462 163, 618, 650, 656 263 638 660 087, 262, 357 350
Moon, S.J. Moradi, W.A. Moran, J.R. Moran, K.M. Moran. P.J.S. Moran, W.J. Mordini, A. More, A. Moreau. J.J.E. Moreau, N. Moreno, A. Moreno-Dorado, F.J. Moret6. J.M, Moretti, I. Moretto, A.F. Morgan, J.P. Morganti, S.
759
064 327,496 160 325 058,331,390 585 131,552 163 055 299 165,467 3 12,495 675 247 117 461 023,033, 519 002, 089, 137, MaiA 150, 177, 185, 193, 447, 459, 484, 694 Mori, K. 505 174, 333, 433, lkhiix 499,582 117, 172 Mori, N. Mori, Y. 198,329 Jvloriartv. R .M . 429 487 h4orikawa, J. Morikawa, 0. 5 15 Morimoto, C. 016, 105, 223 Morimoto. T. 066, 094, 160, 207, 249, 412, 425,455, 538 533 Morinelli, T.A. 379 Morisaki, Y. 344, 681 Morita, M. 25 1 Morita, R. 622, 652 Moritani, Y. 201 Moiiuchi-Kawakami, T. 066 -. J.P. 510, 518, 519, 520, 521, 523 Moro, A.V. 494, 695 245 MOKO,M. Moi~eale,A. 258 Morris, G.A. 138 685 Morrison, A.J. Mortier. J. 010,482 615 Morton, H.E. 210
AUTHOR INDEX
760
Mortreux, A. Moscalenko, M.A. Moser. W.& Moskalev, N. Moskowitz, I I . Moss, W.O. Mossman, C. Mostefai, N.
B.
Motofusa, S.-i. Motorinn, I. Motoyama, Y. Motti, E. Moudy, 1I.M. Mouelhi, S. Moulin, D. Moulton, B. Movam. P.J.S. ~flvass;Ich-&
Mowery, hl.1;. Moyano, A. Mucci, A. Mucciante, V. Muchowski, J.M. Muezelaar, G.J. Muir, K. Mukai, R. Mukaivnma. T.
Mulder, J.A. Muller. P. wuller. M. Jvliiller. P. Miiller, T.J.T.
Muller.P.
Mulvaney, A.W.
053, 322, 323, 400 649 347 296, 618 685 224 351, 360 280 256 057 340, 533, 540, 602 20x 502 030 135, 146 565 498 666 194, 473 698 157 230, 242, 312, 326, 356, 413 142, 149, 151 022, 029, 060, 118, 386, 684 585 263 40 1 130 522 413, 687, 702 563 071, 079, 080, 093, 094, 099, 132, 141, 229, 373, 504, 505, 542, 546, 547, 641, 684 678 488,489 0x6-127 245 486, 541, 546 220 66X 237 279, 281
Myers, B.J. Mys&, P.
671 026 660, 691 329,384 583 173, 249, 331, 379, 425, 435, 672 511, 671 092, 687 622 567, 588 038 249,429 637, 679 353 057, 060, 501,542, 140, 189 373 450 178,568 5 77 003 524 455 097 444 094 161 109,406 124 425 671 054 360 246 458 370
Na, Y. Naasz, R. Nacci, A. Nacci, A. Nadeau, C.
492 197, 199 185, 206, 217 458 014
JLfulzer. J, Muiiiz, K. Muiioz, M.P.
MlKLL
b!fuLL Murakami, N. Murakami, R. Murakami, S.
Muraoka, T. Murase, N. Murata, K.
b!lwhx
Murphy, D.L. Murphy, F.
M!mLJA
Murtaugh, L. Murthy, Ch.V.S.R. Murtuza, S. Murugesan, v. Murugesh, M.G. Mushrush, G.W. Muthukumaran, K. Muto, H. Muto, T. Mutoh, Y. Muxworthy, J.P. Muzzi, R.M.
..
. .
274, 404, 581,
143, 644
AUTIIOR INDEX
Naef. rt
Naeimi, 11. Nagafuji, A. Nagahara, T. Nagai, K. Nagaiah, K. Nagano, T. Nagano, Y. Nagaoka, T. Nagaoka, Y. Nagarajan, M. m a s a k a . T, Nagasawa, K. Nagasawa, M. Nagasuwa, T. Nagata, A. Nagayama, S. Nagle, A S . Nagura, T. Nahmany, M. Naicker, K.P. Naik, S. JVaiini-Jainal. M. Naimi-Jainal, M.R. Nair, L.G.
Nair, R.V. Nair, S.K.
w
Nrtito, M. Yaito. 1 Naito, Y.
UWL.
Nakadai, M. Nakae, Y. Nakagai, Y.-i. Nakagawa, K.
Nakagawa, S. N A ~ ~ *r. ~ w ~ , Nakagawa, Y. Nakahara, Y. Fakai. T. Nakajima, A. Nakajima, K.
030 533 702 122 439 242 235 469, 631, 632 320 664 042, 308 087 006 629 297 497 574 119 534, 543, 545, 546 246, 279, 286 122 630 253,463 076, 126 294 266, 268 376, 646, 705 044, 646 524 334 376, 572, 646, 662, 677, 705 406 268, 295, 518, 597, 598 702 227, 229, 235 124 314 455, 502 518 586, 616 500 239, 506 199 533 345 538 167, 438, 483,
76 1
Nakajima, M. Nakajuna, R. Nakajima, S.-i. Nakalshima, T. Nakamichi, N. Nakarnoto, H. Nakamura, A. Nakanura, H. Nakmiura, I. I. d .m u r a . K, Nakamura, S. Nakamura, T.
Nakano, K. Nakano. M. Nakano,Y. Nakao, J. Nakao, Y. Nakashima, I I . Nakashima, W. Nakata, D. Nakata, K. Nakatani, H. Nakatsuka, Y. Nakaya,
Y.
Nakayarna, M. Nakayasu, T. Nakoji, M. Nunane, C. Namati, N. Namhoodiri, V. Narnhu, H. Nan, Y. Nanda, S. Nandur, V.B.
l&umi&
Naota, T. Napula, A.
619,636, 693 623, 667 436 101 515 079 022 227,312 284,447, 544 198,586, 650 003, 058, 059, 062, 284, 361, 497 189, 697 363, 381, 382, 518 023370 021 207 079, 080, 141, 229 630 249 675, 683 021, 136
on1
380, 486 352 182, 688 315, 629 015 021, 029, 537, 539 116 335 520
122 595 275 690 003 355, 644 070, 512, 517, 584 656 055 018 239.3 72 384 206 652
762
Nara, S. Narasaiah, A.V.
AUTHOR INDEX
277 106 167, 174, 263, 414, 612, 676 . . p’tmhan. S. Pdrd. 018, 383 Narayan, S. 583 Narayanm, B.A. 019 Narayanan, R. 674 Nmnder, N. 084, 373 Narita, K. 400, 673 163, 207 Narkunan, K. Narsaiah, A.V. 107, 419, 689 Narsihmulu, Ch. 261, 700 Narusawa, H. 030 Narvaez, L.D. 480 Naskar, D. 367, 576 Naso. F. 481, 482 Nasreen, A. 051, 416 Nattier, B.A. 392,410 472 Navacchia, M.L. 638 Navmm, M. 123 N ~ v ~ u T o - VA.~ ~ . ~226 , Nayak, M.K. 013, 086 Navak. S.K, 044, 195, 634 Nazari, R. 700, 704 Ndakala, A.J. 545, 661 N&d&lec,J.-Y. 033, 129, 207, 399 Neelukantan, P. 085 002, 638 Negoro, R. 109 Negri, J.T. 159,304 Neidigh, K.A. 297 Neighbors, M. 576 Neimann, K. 360 Neipp, C.E. 581 Neitzel, M.L. 394 220 Nelson, J.D. 253 w o n . S.C,, 318 050,392, 416 Nemoto, T. 350, 352 Penaidenko. V.G, 475, 665 Net, G. 104, 198 Netchitnilo, P. 581 Netland, K.A. 685 Neuhurger, M. 153 Neumann, H. 496 091,360
Neunhooeffer, H. Neuville, L. Nevado, C. Nevalainen. V, Nevar, N.M. Newbold, A.J. NeW~QdL-bL Newton, J.R.A. Newton, T.W. Ng, L.-Y. Nguefack, C. Nguyen, B .T. Nguyen, K. euven. S. .T. Nice, L.E. Nicholson, R.L. Nicklow, R.A. jY~colaou.K.C, Nicolini, L. Nielsen, S.F. Nieuwenhuyzen, Niimi, L. Niimi, T. Niimi, Y. Nikalje, M.D. Nikishin, G.I. Nikje, M.M.A. Niknam, K. Nikolic, N. Nilsson, P. Nilsson, P.A. Nimkar, K.S. Ninomiya, I. NiorB, P.-A. Nishi, T. Nishihayashi, Y. Nishida, A. Nishida, M. Nishida, Y. Nishide, K.
Nishihara, S. Nishihara, T. Nishihara, Y.
M.
165 659 691 317, 519, 543 669 010 365 701 623 328 059, 130 307, 392 514 258 045, 138 579 613, 642 241 602 683 137 142 215,567 232,429 217, 527 674 259,498 525,528 412 098, 531 541 399 192 648 518 3 13 596 300, 491,494 586, 616 174 050, 074 071 082, 491, 595, 626, 660, 703 080,497 252,682 174 002, 150, 185, 193, 459, 484, 694
AUTHOR INDEX
Nishikata, T. Nishikori, H. Nishiinae, S. Nishhnura, A. Nishimura, M. Nishimura, T.
Nishino, K. Nishio, M. Nishioka, K. Nishitani, T. Nishiwaki, N. Nishiwaki, Y. . . ishivaina. FL Nishiyama, T. Nishizaki, Y. Nishizawn, M. Nishizono, N. Nishizuka, A. Nitzan, D. Niwa, I I . Niwa, Y. Nkagami, R. Noack, M. Ntihrega, J.A. Nobunaka, T. Nohutorno, M. Nocanda, X.W. Nocentini, I'. Noda, K.
J+>c1e.M.
Noels, A.F. Nogami, G. Nogami, 11. Noguchi, S. Noguchi, Y. Noji, M. Noji, S. Nojima, M. Nokaini, T.
w.s.' p
177 204, 267, 354 03G 653 259 061, 091, 094, 097, 315, 390, 392, 409, 686 132 607 038 110,036 174, 602 699, 701 478 030, 215 339 154, 306, 339, 348 690
591, 676, 688 173 213 303 159 274, 566 497 173 603 548 553 044 658 036 079, 089 07 1 219, 375 374 548 546 047, 328 610 329 343 022, 442, 555 180, 271 008, 133, 145, 177, 289, 292, 455, 651
763
Nornen, M. Nomura, H. Nomura, 1. Nomura, M. Norhedo, S. Nordin, S .J.M. Norinant. J.F, Norsikian, S . Norsikian, S.L.M.
North..
Norton, D.
Nose, M. Noson, K. Noto, R. Notz, W. Nourozi, A.R. Novik, T. Nowak, P. Nowogrocki, G. JVovori. R.
PJozaki. J L Nozawa, A. Nozawa, K. Noziri, M. Nsenda, T. JVudelrnan. N.S. yucent. W.A, Nunn, M.I.T. Nury, P.
OBrien. P. OMahony, C.P. I
.
Oakes, K.S. Opherger, M. Ohora, Y. Ocal, N.
101 091 413 035, 121, 184, 221 019 067 181, 184, 187, 190, 231, 408, 614 187, 190 345 599, 600, 648, 649 191 27 1 477 053,542 430, 437, 526 022, 501, 604 101 194 467 323 011, 160, 207, 328, 393, 474, 499, 501, 516, 537 063 252,682 524 640 254 393 3 19 370 220, 237, 245
154,558 349 701 464 147 406, 435 260 581, 616
764
Qchiai. Ochiai, Y.
QdiLL
Oda, N. Oda, Y.
Odagaki, Y. Odaira, M. Odashima, K. Ogasawara, M.
Qeawa.A.
Ogawa, c. Ogawa, R. Ogawa, 'I.. Ogawa, Y. Ogawa. L. ogo, T. Oguni, N. Ogura, M. Oh, B.H.
QbL& Oh, C.R. Oh, D.H.
Qh&x.
Oh, K.S. Oh. T. Ohaishi, Y Ohara, S. Ohashi, K. Ohe, K. Ohe, T. Ohfune, Y. Ohga, M. Ohga, T. Ohgo, Y. Ohi, D.H. Ohigashi, N. Ohishi, 'I.. Ohishi, Y . Ohkoshi, N. Ohkubo, K. Ohkuma, T. Ohinori, 1.1. Ohmori, K.
AUTHOR INDEX
039, 639 392, 416 173 244 384 569 214 117, 404 087 185, 194, 200, 201, 428, 631, 632, 678 508, 510, 621 273,573 119 128, 596 406 289 404 136 539 052 168, 170, 198, 586 006, 116, 432, 459 048 168, 621 692, 704, 707 186 620 497 520 159 086 097, 208, 409, 414, 686 208, 414 043 022,555 023 023 444 409, 704 121, 131, 149 156 455 457 160, 516 044, 562 299
Ohnesorge, M. Ohno, A. Ohno, €1. Ohno, K. Ohno, T. Ohsawa, K. Ohshima, T. Ohshita, J. Ohsima, T. ohsugi, s.-i. Ohta, C. Ohta. T. Ohtaka, A. Ohtaka, K. Ohtaka, S. Ohtan, S. Ohtsuka, Y. Ohwada, A. Ohya, K. Ohyahu, Y.
u
Oixhide, M. Oishi, M. Oishi, S. Oishi, T.
I2iuL-L Okahe, T.
Qkada. Okada, S. Okada, Y. Okajima, M. Okamoto, 11. Okamoto, I. Okamoto, K. Okamoto, M. Okamoto, S. Okamoto, T. Okamoto, Y. Okamura, T. Okano, K. Okano, N. Okauchi. T, Okawa, M. Okazaki, H. Okeda, T.
613 062 035, 043, 442, 511,590, 619 306 082, 626, 660, 703 421 200, 207, 350, 502,535 641, 644 352 07 1 354 056 044, 128, 288, 608 428,536 126 505 237 193, 535 277 569 283 135, 245,552 338 353 569 442 120 183,562 316 367, 564 591 235 298 591 024,504 123 204, 340, 428, 460,553 044 502 611 057, 143,501 521 607, 707 159 563 177
AUTHOR INDEX
Okhnoto, Y. Okino, T. Oku, A. Oku, K.4. Oku, M. Okuho, I-I. Okuda, S. Okumoto. H. Okumura, K. Okuyama, S. Okuyiuna, Y. Olilh. G.A. Old, D.W. Olivares, C.M. Olivella, S. Oliveii, 1. Ql1Vo. J-Lfi, Ollivier. C.
Ollivier, J.
Olmstead, M.M. OlOfSSClnJ1.
Olofsson, K. Olsen, .l.-C. Olson, R.J. Qlsson. & Omat;r, Y . Omino, K. Omoto, M. Onishi, Y. Onitsuka, K.
Ono, I:.
otlo, Ir.
Onomura, 0. Onoue, T. Onozawa, S.-y. Onuma, Y. Ooi, T. Ootsuka, K. Oppici, G.
Oppolzer, W
Orita. A. Orito, K.
643 595 433, 626 528 433 003, 623 117 661 252, 682, 682 023 250 665 02 1 073, 398, 470, 4x0, 482, 574 29 1 176 118 528 699 049, 208, 209, 323, 625 262 155 517 610, 617 620 373 463 622 006, 663 447 371 2x8, 629, 633, 636 109 1x3, 210,562 065, 081, 273 097,409 62 1 286 021, 251, 311, 318, 323, 337, 4X7,543,598 267 615 550 008, 074, 082, 320 2x7
765
..
Onvama. 4. Orizu, C. Orlinkov, A. Orsini, F. Osawa, E.
Oshita, M. ov. Osnahrug, S.J.M. Osswald, T. Osterhout, M.11. Osterle, C . G . Osuna, A.M.B. Oswald, M.C. Ota, M. Otaka, A. Otake, €1. Otera. J.
s,x
Ottenwaelder, X.
x.
Ou, Ournirnoun, 11. Outrarn, R.J. Ouugh, A.J. Qvennan. L.E. Owa, T. Owen, J.M. Owens, G.S. Owens, T.D.
oya,
s.
.
.
Oyiunada, J. Oyler, K. Ozaki, 11. Ozdeiiur, I. Ozgiil-Karaaslan, E.
077, 079, 080, 086, 089, 365, 655 649 319,329 353 619 01!6 036, 049, 138, 144, 146, 179, 188, 320, 346, 363, 381, 382, 400, 428, 446, 468, 487, 507, 509, 511, 530, 531, 534, 575, 603, 663, 693 672 612 247 138 134 661 561 100, 108, 110 613 569 622 008, 074, 082, 320 068 402 261 674 333 572 682 189, 577, 590, 644, 646 607 264 359 514 567, 588 434 455 569 475 298, 654 434 125
766
AUTHOR INDEX
€kL
Pace, P. Pachamuthu, Pacut, R. Pae, A.N. Page, M.A.
K.
Pagni, R.M. Pagnoni, U.M. Paik, s.-J.
l3lkL.L
Palazzi, C. Palco, M.R.
€hkL
Paleta, 0. Palmer, M.J. palnnieri. G , Palomero, M.A.
Phmies, 0.
IkLX.
Pan, Y. Panarina, A.E. Panaro, S.A. Pandey, R.K. Pandey, S.K. Pandya, S.U. Panicker, S.B. Panja, C. Pannala, M. Panunzi, B. pununzio. M. Panyella, D. Papa, P. Papageorgiou, E.A. Paparin, J.-L. Paquin, J.-F. Paras, N.A. Paraskar, A.S. Pardi, S. Pardo, c.
, ;<
361 208, 640 08 1 394 132,554 464 349,354 003, 006, 151, 483, 488, 601 561,585 438 269 330 028 005, 493, 494, 657 660 370 341, 654 027 678 338 104, 198 023,024 193 700 220 314, 362 109,573 419 47 1 190, 657, 659, 664 646, 662 627 192 084, 646 530 248 086 309, 542 570 570 464, 659 446 194 473 499 033 514
Parello, J. Parikh, V.A. Park, C.S. Park, D.J. Park, H.
hLEi4
Park, H.-J. Park, H.S. Park, J. Park, J . 4 . Park, J.-S. Park, J.K. Park, K.H. Park, L. Park, M.-k. Park, M.Y.
Park, R.J. Park, S.-B. Park, S.-T. Park, S.W. Park, Y.-S. Park, Y.S. Park, Y .T. Park. Y.S. Parker, D.G. Parlier, A. Pannee, E.R. lliiaLu
Parrini, M. Pmish, C.A. Parrish, J.P.
Parsons, M. Parsy, C.C.
RalYaJL
Parvain, J.-L. Pasha. M.A.
-p
Pasquier, C. Pastor, I.M. Pastori, N. Pastro, I.M. Pastukhov, F.V. Patel, P.
260 236 136, 596 229 587 5 95,5 97 054 525,557 686 064, 596 366 671 228 382 595 525 372, 627 277 679 113 350 625 246 118 595 161 623 280 009,499 190, 325,694 697 289,341, 341 222 083, 152, 192, 243, 575, 578, 654 374 563 361 229 499 100 383 053 034, 036, 206 063,415 496 269, 270 076, 126, 318 332
AUTHOR INDEX
Patel. R.N, Patel, S.T. Patel, Z.D. Pathak, D. Patil, P.N. Patonav. T, Patro, B. Patrocinio, A.F. Patti, A.F. Paul, s. Pauls, H.W. Pavia, A.A. Payen, A. Payerar, A.M. Payne, A.11. Payne, B.J. pearson. W.Ft Peat, A.J. Pedregal, c . Pedro. J.R Peelen, T.J. Peerzada, N. Pei, B.-G. Pei, T. Peiffer, G. Pblinski. 1.. J’ellacani. L. Pellet-Rostaing, S. Pellhn, R.F. Pelotier, B. I’elia, D. Pendola, K.A. Peng, 1. Peng, S.-M. Peng, I’eng, Y. Peng, z.-z. Penieres-Carrillo, G.
x.
ett.
c.s*
Pcnso, M. €kLwc Perales, J.B. Perch, N.S. Perciaccante, R. I’ereira, A.K. I’erez, M. Pbrez, A. Pbrez, D. Perez, E. Pbrez, I.
018 350, 351 567 302 524 060 568 331, 390 287, 363 103 146 08 1 326 390 540 100 300,302, 583 149 214 06X, 412 395,515 318 286 338, 421 072, 177, 667 055 025,053 258 184 499 394 07 1 338 260 668 472 228 106 685 612 151, 253 112, 548 176 466 596 067 227 515 149 650,653 136, 150
PBrez, P.J. Pbrez-Andrbs, J.A. PBrez-Encaho, A. PCrez-Prieto. J, Pbrez-Serrano, L.
. \ pencas. M .A_. Pbrichon, J. Peron, G.
hKi!dL
Perry, M.C. Persons, T.
Peruncheralathan, S. Pesti, J.A. petasis. N.A. Pete, J.-P. Peters. Iz Peterson, J.A. Petit, A. Petra, D.G.I. Petricci, S. &lg&AA. petroski. R.J. Petrovski, Z. Petrovskii, P. Pettersen, D. Pfaltz. A. Pfeiffer, D. Pfeiffer, S.S. Pfister, X. Phansavath, P. PheIps, B.S. Philips, N.G. Phillips, A.M.F. Phillips, J.11. Phukan, P. Piao, D. Piamlli, U. Piber, M.
767
212 587, 637, 666 674, 676, 680, 688 395,515 212 676, 680, 688 124, 226, 284, 405, 564, 680 022, 029, 060, 118,386, 684 033, 129, 207 191 47 1 113 648 168, 169 162 005 073, 482, 567, 611 600 142 596 287 064, 067 151, 253 014 570, 604, 671, 681 442 541,538 319, 329 553 153, 158, 199, 284, 445, 489 070 381 054 054 55 1 613 332 482 486 064 011 04 1 150 325
AUTHOR INDFX
768
Pieraccini, D. Pierce, M.E. Piermatti, 0. Pierohon, M. Piers. E, Piers. W.E. Piersanti, G. Piet, J.J.N. Pietrantonio, S. Pietrusiewicz. K.M. Piguel, S . Pike, K.G. Pilato, M.L. Pillai, P.M. Pillon, F. Pilo, I,. Pinchart, A. Pinchuk, A.N. Pineda, 0. Pinetti, A. Ping-Guo, M. m > e Melo. Pinkerton, A.B. Pinna, F. Piras, E. Pirguliyev, N.Sh. Pisaneschi, F. Pisano, L. f’istarh, V. Pitre, S. Pitre, S V. Pitter, S. Pittinan Jr., C.U. Pitts, M.K. Piva. 0. Pivas, E. Pivsa-Art, S.
r?lzmJ‘ Plancher, J.M. Plaquevent, J.-C.
u!ai
Plotkin, M.A. J’lumet. J. Plunian, B.
662 004, 061, 467 526, 554 204 086, 240 248 509 512 482 446 092, 685 163 423 381 100, 272 048 026 083 5x5 707 301 437, 550, 678, 686, 108 272 495 073 262 379 415 053 327 615 025 087, 262, 634 100 184 157 045, 074, 467, 532 112 372 274 188 299 237, 508, 010 356
665
Yodlech. J. Poehlein, B.W. Poh, S . Pohl, M. Pokier. D, Poisson, J.-F. Pojarliev, P. Polhorn, K.
PYuL
Poliskie, G.M. Pollastri. M.P. Pollet, P. Polniaszek, R. Pons, J.-M. Pooyan, M. Porcelloni, M. Porchedda, A.
617, 692
porta. 0. Portella. c. Porter, D.W. Porter, J.R. Porter. N . h Portlock, D.E. Porto, A. w r . G.U, Poss, M.A. Postsel, M. Potdar, M.K. I’otier, P.
€!QmAbL Potts, D.
357
302,
527
Poulin, 0. Pourbaix, C. Pourhahih, A. Powell, D.A. J’ozzi. G. Prabagaran, N.
Rabhakxan, E.N. Prabhxasuth, R . Prahhudas, B. Pradaux, F. Pradeille, N. Prager, R.11. praianati n
259 35 8 474 541,546 630 190 197,534 320 07 1 131, 236 378 367 191 247, 252 677 531 341,654 091, 018, 091, 387 063,415 532 154 266, 272 148,589 075, 243 359 331 285 013 315 307, 602 017 567 203 032 094 572, 485 059, 128,464 601, 645 569 299 426 037 026 357 230 108, 114, 262, 301, 302, 338, 423, 441, 471, 606
AUTHOR INDEX
Prakash, G.K.S. Prakash, 0. Prakash, P.K.S. Prakash, S.J.
l?rudl&
Prasad, A.R. Prasad, A.R. Prasad, B.A.B.
Prasad, R.S. Prasad, T.R.
Prashad. M, hathap, I. hlLL
Preiss, T. Prenzel, A .I 1.G.P. Prestat, G. Price, D.A. Priego, J. Priepke, 1I.W.M. Prieto, I-’. Primault, G. 1.
Pringle, W. Probst, D.A. Procelloni, M. Procopio, A. I’rocopiou, P.A. J’rocter. D.J. Prodger, J. Proto, A. Przyhorowski, J.
43L-L Pu, Y.
Puerta, M.C. Pugh, G. Pugh, R.I. Puij aiier, C .
Punniyamurthy, T. Purkiss, D.W. Purpura, M. Purpura, M. Py, s. Pytkowicz, 11.
073, 398, 470, 480, 574 102 429 560 700 653 23 1 701 573 373 279, 281 075, 083 010,308,592 573 423 247, 250 490 585 047 413,585 024 62 1 165 400 197, 332 514 243 238 184, 370, 548 460 522 584 355 648 029, 042, 070 669 312 324 332 060 204 120 481 052 55 1 43 1 438 47 1 196
Pyun, D.K.
Qian, rr. Qian, X. Qin, J. Oinf. F.Ia Qiu, G. Qiu, M. Qu, Z. Quach, T.D. Quan, L.G. Qukguiner, G. Quesnel, Y. Quici, S. Ouintcro. L. Quirante, J.
Kaahe, G. Kabhat, P. Raheyrin, C. Raddy, G.S. Radhakrishna, P. Radhakrishnan, K.V Kadhakrishnan, U.
Radigue, A. Radinov, R.N. Radivoy, G. Radke, K.R. Raeppel, S. Rafei, M. Raghavan, K.V. Rahun, Md.A. Kahman, A. Kahman. A.-u.
769
136
351,599, 700 492 228 273 171 419 317 214 408 222 043, 064, 068, 118,394, 559 139 086, 112 059, 095, 128, 464, 288, 490 148, 515 242
021 368 130 088 087 146, 169, 172 115, 173, 436, 493 376 550 151, 236 289 400 078,084 373 653 383 275
770
AUTHOR INDEX
Rahman, S. Rahman, S.M.A. Rai, A.N. Raj, K.S. Raja, T. Rajagopal, D. Rajagopal, R. Rajaiah, G. Rajaram, S. Rajkuinar, G.A. Rajkuinar, M. Rajzman, M. Rakesh Rakhit, S . Rakotoaiisoa, €1.
RanA’
lbImJ&
Rain, S.R. R m a , K. Rmachandar, T. Riunalinga, K. Ramana, K.V. Ramarao, C. Ramesh, C. Rainesh, G. Ramesh, N.G. Ramesh, P. Rameshkumar, C. Rami, ILK. Rhnila, A. Rammingcr, C. Ramnauth, J. Ramontlcnc, Y. Raincis, E.C. p a i m s . J .M.R , Rampa, A. Rana, K.K. Randal, S. Randall, M.L. Randl, S . Ranganathan, K. Rangnekar, D.W. Ranier, J.D.
V.
304 043 084 608 303,455 231,701 305 674 459 344,588 477,560 073 097 074 677 076 203 308 367 255 301,305 100 082,399 053,319, 647 447 230 106, 111, 424, 601 099 007,563 075, 185,418, 585,638 367 355,667 620 488,489,680 291 508 462 203,215 188 205 705 339 371,642 457 687 456,675 299 603 617
Rankin, E.M.
Rao, A.B. Rao, B.S.
l.ha.x Rao, G.V.
IhxLHsE lhLL&L EhfLKJL
Rao, M.L.N. Rao, M.V. Rao, N.V. Rao, P.B. Rao, R.J. Rao, R.S. Rao, T.P. Rasheed, M.A. Rasmussen, M. pasmussen. S.C. Rasparini, M. Rassias, G.A. Rassu, G. Ratcliffe, P.D. RatovelomananaVidal, V. Raugei, E. Rault. s. Rausch, B.J. Ravikumar, K.S. Ravindranath, N. V.H. Ray, C.A. Rayahamp, D.K. Raymond, M.-N. R i m , A. Razin, V.V. Ready, J.M. Reheiro, G.L. Recupero, F. Reddy, B . peddv. B.M.
680 013,079, 085, 171, 192, 371, 571,650,696, 702 055 305 084,088 073,084,265, 303 164 057,059 084,516, 566 135, 151 106 085 351,353 077,300 235 342 280 019 289 558,587 004,490 349,354 547 092 054 323 405 673 102, 633,653, 665 509 075 150,238 614 576 685 464 319 321 501 401,614 056 092 701 325,415
77 1
AUTHOR INDEX
Reddy, B.V.S.
Reddy, C.D. Reddy, Ch.K. Reddy, Ch.R. Reddy, Ch.V. Reddy, D.S. Reddy, E.J. Reddy, E.V. Reddy, G.J. Retldy, G.S. Reddy, G.S.K.K.
lk&LiY-
Ik4dm.L Reddy, K.B. Reddy, K.S. Reddy, L.K. Reddy, M .A. Reddy, M.M. Reddy, M.R. Reddy, M.S.K. Keddy, M.V.
Reddy, M.V.R. Reddy, P.G. Reddy, P.P. Retldy, P .S.M.M. k d d v . P.S.N, Reddy, P.T. Reddy, S.1-I.K. Reddy, V.L.N. Reddy, V.R. Reddy, Y.K. Bedinan. A.M. Redpath, J. Redy, B.V.S. Reed, A.D. Reek, J.N.11.
047, 083, 109, 206, 235, 280, 342, 424, 525, 601, 641, 23 1 23 1 683 077, 300 704
078, 082, 088, 106, 111, 130, 209, 231, 270, 275, 302, 303, 417, 418, 499, 524, 573, 584, 605, 614, 701
106, 267,
Of 1, 084 082,301 112 458, 531 044, 085, 086, 114 130 303 073, 265 23 1 029,563 084,516, 566 084, 516, 566 302, 659 405 395 082, 106, 262, 287, 563, 588 319, 327 249 01 f 111 01 1 055, 082, 209, 418, 499, 615 465 620 325, 415 139
171 5x9 615 5x9 064, 293
Rwse, 0.
IhLbLX Reeves, J.R. Regis, D. Reginato, G . RBgnier, S. Regueiro-Ren, A. Rehhorn, D.C. . . lI.-lJL Reid, S.N. Reider, P.J.
Rein, T . Reis, 0. Reisch, H.A.
IkiwLL . . H.-[J Rele, S. Remeshkumar, C. Ren, 1L-J. Ren, L. Ren, P. Ren. R.X. Ren, S.-K. Renard, M. Renaud, J.-L. & m u d . P. Renault, 0. Renehan, M.F. Renga, J.M. Renz, M. Repic, 0. RepiE, 0. Resouly, S.M. Revial, G . Reymond, S. Reynolds, D.J. Reza-Elahi, S. Rezaei, 11. Rezai, N. Rheault, T.R. Rheingold, A.L. Bbo. H . - L Rhyoo, I-I.Y.
l3mLQ
200 158, 194, 402,403 351,360 660 552 263,704 017 149 440,645 519 010, 163, 259, 273, 302, 425, 577 441 125
509
265,
164, 299, 487,
022,441 344,412 308,450 226 587 015 153, 632, 658 261,367 542, 668 395 503,555, 557 049, 208, 209, 323, 469, 625, 641 405 349 264 332 010,373 083, 308, 308, 592 147, 152 581 531,533 62 1 073 614 084, 260 176 580 044, 397 054 057,503
772
Ribe, S.
RiddL
Richards, S.J.
Riela, S. PieraL Rienneier, T.1-I.
Righi, P.
IULR
Rinaldi, S. Risberg, E. Kisch. N. Rische, T. Rise, F. Risgaard, T. Rivera. A. Rivera, R. Roherts, E. Roherts, R.S. Boherts. s.M, Bohertson. J. Rohin, S.
Rohinson, J.E. Rohinson, K.E. R ~ )'r.~ ~ , Kocamora, M. Roche, D. Rochon, F. Rodrigues, J.A.R. Rodrigues, O.E.D. Rodriguez, A.L. Rodriguez, A. Rodriguez, D. Kodriguez, J.F. Rodrieuez. M.A. R o d i i g ~ e ~ - R a ~ eC.r a , Rodliguez-Solla, H. Rodriguez-Vicente, A. Roels, J . Roesch, K.R.
AUTHOR INDFX
045 262, 556 353 328,358 677 049 526 022, 029, 060, 118, 386 158, 271 326, 458, 462 445, 512, 528, 533, 666 110, 609, 706 460 360 068, 503 072 614 607 298 685 699 684 299 26 1 443 350, 352, 354, 355 436 094, 576, 643 252, 253, 672 243 397, 604 OX6 373 330 058, 157 310,494 , 632 422 101, 690 226 37 1 168, 276, 593 033, 234 587 ,637 033, 234 280, 622 164, 173, 285, 610
Roger, P. Rogers, M. Rogge, T.M. Roh, E.J. Roje, M. Rolando, C. Romariski, J. Romao. C. Roinera, J.L. Romero, D.
EQmQAL
Roncaglia, F. Ropartz, L. Roque, J.-P. Roques, N. Rorer, J.R. Rosati, 0.
Roschangar, F. Rosehlade, S. RosellB, A.L. Roses, J.B. Rosingana, M. Ross, J. Rosset, S.
Rossi,&
Rossi, L.I. Rossi, M.
Rossier, J.-C. Rosso, G.h. Rotello, V.M. Roth, B.D. Roth, P. Rothstein, S.D. RottlPnder, M.
lkudmJ.
b h . W.B. Rousseau, B. pousseau. G. R O U S S ~J.-F. ~U, Rousset, L. Rousset, S. Roussey, E. Rovis, T. Roy, A.
275 686, 694 585 048, 188, 353 337 196 666 652 349 332 381,387 644 268,311, 318 561 660 08 1 478 307 083, 085, 088, 109, 516, 575, 649 134 436 068 682 247 024 410 195 248, 263, 338 475 083, 085, 649 138, 323, 636 220 664 140 267 067 289 150 261 026,359, 485 381, 534 094, 313, 576, 643, 667 307 207 190 275 485 452
AUTHOR INDEX
Roy, C.D.
IQ.Gi IbGx. Royer, S.
Ru, %. Kuano. J.I..G. Ruano, M. F. Rubin, M. Kuhina, M. Buhinov. D.B. Kuhinova, I.L. Rudheck, I-I.C. Rudd, M.T. &lcJcdL Rudloff, I. Rufanov, K.A.
KulLA'
Kuiz, R. Rulev. A.Yu. Rumho, A. Russell, A.E. Russell, G.A. Russo, M. Rutjes, F.P.J.T. Ryan, K.M. Qchnovsky&Q Ryu, 11.-c.
RYL.L
Ryu, J . 3 . Ryu, K.
Sah, c. Saahy, S.
Sahhani, S. Saliitha. G .
Sahnis. K.W.
Sahu, K.K. Sachinvala. N. Sadavarte, V.S.
448 032, 367, 576 366, 371, 642 266 624 65 1 705 452, 460 474 115, 121, 129 493 669 669 237 69 1 623 23 1 219 104, 127, 197, 198 068, 412 598 004 523 703 525 453, 586, 591 349,354 392, 642 001, 002, 222, 224, 399, 411, 553 250, 327, 361 276 192
226 570 703 074, 087, 088, 112, 130, 206, 270, 275, 395, 601, 605, 659 603 424 269 019, 075, 095, 322, 367, 424
Sadayori, N.
Sadeghipur, M. Sadighi, U.P. Sadvarte, V.S. Saeki, K. Saeki, N. Safaei, H.R. Safari, J. Sagal, J.F. Sagar, A D . Sage, M.A. Saha, B. Saha-Miiller. C.R.
Sahara, T. Sahlin, 11. Sahu, P.R. Sahu, S.G.
. ."., ,.
Said, S.B. Saidi. M.R,
Saikia, P. Saint, R.E. Saint, S.L. Saint-Clair, J.-I;. Saiparakash, P.K. Saito, A. Saito, B. Saito, H . Saito, J. Saito, K.
Saito, T. Saitoh, A. Saitoh, M. Saitoh, T. Saiiki. HZ Sakagami, Y. Sakaguchi, K.-e.
773
173 105, 111, 166, 168, 281, 282, 605 124 291 389 034 216, 451 475 605 367 075, 312,471 361 213, 214 051, 351, 353, 391,545 065, 570, 579 610 108 627 538,541 016 089, 093, 102, 257, 266, 268, 593,596 658, 683 471 236 236 136 477 021, 240 475 204, 626 653 546 041, 115, 162, 198, 225, 273, 283, 439, 455, 500, 529, 564, 586, 611, 650, 694 025, 340 207 080 07 1 063,161 336 125
774
Sakaguchi, S.
Sakai, A. Sakai, D. Sakai, M. Sakaihara, N. Sakairi, M. Saknkura, Y. Sakamaki, Y. Sakamoto, K. Sakamoto, M. Sakamoto, S.
Sdkdmnto.. -. . Sakiunura, 11.
Sako, T.
Sakthivel, K. Sakuma, S. Sukurada, I. Sakuragi, R. Sakurai, 11. Sakuratani, K. Sala, G.D. Salaskar, A. Salaun, J. Saleh, S.A.
Salehzadeh, S. Salerno. G , Sales, M. Salgado, N.R. Salhuddin, S. Saluzzo, c. Salvadori. P.
AUTHOR INDEX
014, 051, 097, 101, 102, 174, 191, 358, 359, 383, 391, 393, 408, 409, 478, 518, 520, 564, 602, 623, 630, 643 685 543 209, 622, 626 433 340 368 532 082 025, 027, 125, 126, 127, 129, 130 537, 652 036, 086, 268, 277, 361, 421, 515, 518 297 504 022, 182, 604 194, 208 071, 533 429 016, 105, 133, 208, 223, 414, 62 1 518 359, 525 5 20 262 507 084, 092, 093, 230, 260, 345, 526 473 169, 310, 587, 661 549 579 301 530 315,414,524 184 196
Salvatore, R.N. Salvi, N.A. Salzhrunn, S. Slunajdar, S.
M
Samanta, S. Samanta, S.S. Slunhaiah, T. Samhri. L.
Samimi, I.I.A. Sammis, G. Siunpedro, D. Sampson, P.B. Samuel. EL Sanchez Jr., G.V. Sanchez, C. Sandherg, M. Sanders, C.J. Sunders, W .J. Sanderson, W.R.
Sandrinelli, F. Sanganee, H.J. Sangiorgi, G. SuiiiGre, L. SannicolZI, F. Sano, T. Sans, J. Sansano, J.M. bantanleu Santelli. Santhi, V. Santi, C. Santoni, G. Santora, B.P. Santos, M. Santos, R.P.
234, 246, 241, 279, 286, 306 054 073,482 110, 296, 390, 472 418 371, 696 280 576 068, 184, 210, 368, 503, 504, 506, 548, 604, 681 092 527 276 286 079 183 337 630 215,376 482 361 176,374 020, 029, 108, 114, 171, 262, 301, 302, 338, 384, 423, 441, 448,471, 606 47 1 241 572 258 546 151 086 421 235,589 073 028, 133, 137, 139, 288, 325, 457 057,059 622, 649 441 193 371 410 371
AUIIIIOR INDEX
Sapinaz, S. Sapra, P. Sarahi, S. Sarandeses. L.A, Saravanan, P.
Sardarian, A.-R. Sarkar, A. Sarina. J.C.
Sarvari, M.H. Sasai. H. Sasaki, H. Sasaki, M. Sasaki, Y. Sasmal, P.K. Satately, E.S. Satchmoen, V. Sathe, V.T. Sato, A.
SiLuL Sato, I. Sato, K.
Sato. K.-i. Sato, M. Sato, s.
Sato.
T.
Sato,
Y
Satoo,
Y.
Satsumahayashi, K. Satti, N.K. Sauer, S. Saulatha, M.S. Sauriat-Dorizon, 11. Sauv6, G. Savage, G.P. Savall, B.M. Savarin, C. Savic, V.
628 292 108 136, 150 076, 086, 111, 113, 140, 457 703 028 013 074, 085, 108, 267 110, 416, 609, 615, 635, 706 230, 266 524, 544 486,539, 653 046, 100 132, 407 107, 285 465 577 698 328 116, 204, 340, 428, 430, 436, 553, 557, 679 025 011, 381, 383, 393, 474, 528, 639 510 213 057, 060, 124 109, 110, 237, 314, 459, 559 172, 200, 433, 450, 567, 670 674 035, 121, 184, 221, 468, 561 588 050,074 248 513 423 429 315 307 485 134, 398 558, 637
Savienac. M, Savignac, P. Sawada, A. Sawada, D. Sawaguchi, M. Sawana, Y. Sawatmi, N. Sawyer, R. Saxena, I. Sayed, S.H. Scanio, M.J.C. Schatz, J. Schaus, J.V. Schaus, S.E. Scheffer. J.R, Scheffler, J.-L. Scheidt, K.A. Schildknegt, K. Schilling, M.B. Schinnerl, M. Schipper, D. Schiimer, H. Schlama, T. Schlununer, B. Schinickler, H. Schmidt, S.E. Schmidt, S.E. Schmitt, A. Schmitt, A.C. Schmitt, M.11. Schmitt, M.J. Schnutzler, R. -eider. C, Schneider, P.H. Schneider, R. Schneider, S. Schnider, P. Schnyder, A. Schohert. R. Schoemaker, H.E. Scholl, M. Scholte, A.A. Schijn, M. Schotten. T.
775
139,453 703 381 548 370, 662 398 058 383 102 267 5 10 677, 681 425 657 648 164 348 322 620 509 256 354 022 064 462 558 575 514 438 171 279 286 344, 440, 645 255 072 212 489 045, 046, 047, 200, 539, 564 030 139, 141, 290, 382 138 246 254 215, 231 064, 453, 591 461 243 030 149
AUTHOR INDFX
776
Schrader, W. Schreier, P. Schreirer, P. Schrock, R.R. SchrGder, J. Schroeder, G.M. Schroeder, J.D. Schuhert, T. Schulte II, J.P. Schultz, A.G. Schultz-Fadeiilrecht, C. Schulz, E. Schurnann, W. Schiirer, S.C. Schuster, M.F.11 Schutte, S. Schwan. A.L. Schwarz, I. Sclafani, J.A. Scoccitti, T. Scott, D.A. Scott, J.S. Scott, K.
ssaLL Scott.
W.J.
Sealy, J.M. Seayad, A. Sehti. S, Seconi, G. Seddighi, B. Seddon, K.R. Seerden, J.-I’.G. Sefeeiin, M. Seger, A. Segorbe, M.M. Segovia, A. Segura, R.C.M. Seiche, W. Seidel, G. Seidel, M. Seitz, J. Seitz, M. Sekar, G. Sekhar, K.C.
SGkLAL
402, 403 05 1 371, 374 05 1 454, 460,465 343 408 389, 517 486 227 066, 325, 382, 464 232 55 1 059,060 478 275 463 621 478 482 057 146, 542 240 193, 540, 548 680 404 215 171 355, 359, 361, 475, 525 508 016 674 262 345, 526 466 565 462 06 1 46 1 333 058 105 004 692 214 022 279,517, 594 305, 525, 659 627
Seki, T. Sekiguchi, A. Sekiguchi, T. Sekimoto, E. Sekine, A.
SdaLL Sell, T.
w
Selvkurnar, K. Selviunurugan, V. Selvi, S. nle. J.E.
SaAL Sen, S.
Senanavake. C.H. Senboku. IL
Senda, T. Senthilkumar, P. Senzaki, M. Sera, G. Seradj, H.
Sercel, A.D. Serdyuk, L. Serino, C. Seiita, K.-i.
&-pJ&
Serva, L. Servino, E.A. Seshadri, 11. Seshnande. V.H. Sestelo, J.P. Seth, P.P. Sethuraman, M.R. Setiadji, S. Setiadji, S. Settambolo, R. Seyferth, D. Sezen, B. Shabangi, M. Shadakshan, U. Shahi, S.P. Shaikh, N.S. Shakespeaare, W.C. Shamsipur, M.
317 002 510 249 200
295 065 353 593 395 169,586 5 14 455, 496 120 304, 629 287, 367, 447, 468,495 194, 201 395 419 455 5 73 111, 112, 113, 114,315 267 694 246 232 163 017 275 224 675 696 136, 150 270 403 173 345 457 45 1 627, 628 205,433, 675 399, 403,475 508 195, 634 327, 414 608 243 166
AUTHOR INDEX
Shanmugasundaram, M. Shao, C: Shao, J. Shao, L.-X. Shao, L.-Y. Shao, M.-Y. Sharadn, D.S. Sharief, V.A. Sharifi, A. Shaiina, A.K. M,
Sharma, L. Sharma, M. Sharma, R.P. Sharma, II. Shaiina, V. Shamless. K.B. Shastin, A.V. Shauehnessv. KJI. Shaw. A.W. Shchetnikov, G.T. She, X. Sheeha, V. Shekaniz, M. B e l c h . K.A. Sheldrake, 1’. Shelly, D.P. Shen, 13. Shen, C. Shen, 11. Shen, J. Shell, J.-h. Shen, K.-14. Shen, I,. Shen. W. Shen, X. Shen, Y.-M. Sherlock, A.E. Shezad, N.
ShlJYL
117 155 216 492 106 025 180 230, 266, 531, 533,555 669 257, 294 625 075, 076, 080, 083, 087, 553 013,077, 086 095 020 077, 170, 171 429 512, 513, 514, 593 665 134 295 612 352, 353 376,572, 646 346, 549, 644 248, 330, 355, 356, 357, 361, 362, 390, 392 276, 617 511 438 496 692 030 023 326 174, 492 145, 150, 216, 484 028 247 584 464 013, 026, 030, 247, 258, 531, 540, 543, 551, 578
Shi, Q.-Z.
ShLX Shi, Z. Shia, K.-S. Shibakiimi, M. Shibasaki, 11.
Shihata, I.
Shibata, J. Shihata, K. Shibatomi, K. Shihli, A. Shibuya, A. Shibuya, I. Shibuya, K. Shieoya, Y. Shiga, N. Shih, Y.-K. Shiina. I. Shiino, K. Shikaura, J. Shim, J.-G. Shim. S.C.
Shim, W.11. Shimada. S, Shimada, T. Shimada, Y. Shinamura, T. Shimazaki, R. Shimizu, If. Shimizu. K.
777
405 416 193, 351, 352, 353, 354, 360, 490, 625 635 156, 673 618 011 071, 200, 207, 350, 352, 502, 533, 535, 537, 544, 548, 607, 647, 648, 704 032, 066, 090, 192, 267, 292, 381,388, 409, 547,607, 682 546 033,041, 556 032, 223, 626, 671 129 137 619,652 618 364 042 272 221 229, 542, 546, 547 429 244 242 052, 167, 168, 170, 251, 275, 277, 318, 406, 621 188 135, 151 002,428, 438 610 546 140 520, 522, 608, 682 499
778
Shimizu, M.
Shimizu, R. Shimizu, Y. Shimoda, K. Shimonaka, K. Shimonishi, K. Shimuzu, M. Shin, S.I. Shin, Y.-J. Shinada, T. Shinde, N.A. Shindo. (I. Shinobulo, H. Shinohara, T. Shinokuho. H.
&ioiri. T, Shioji, K. Shiotsuki, M. Shiozawa, M. Shirai, J. Shirai, M. Shirai, Y. Shiraishi, D. Shiraishi, 11. Shiraishi, 11. Shirakawa, K. Shiraki, I i . Shiro, M. Shirzi, J.S.
AUTHOR INDEX
041, 065, 274, 300, 342, 348, 364, 508, 524, 533, 538, 566, 570, 579, 596, 597, 600, 618, 676 002 056, 407 315, 627 388, 457 191, 398 136 368 033 571 234, 246, 279 027 043 312,471 450, 567, 670 588 446 331,332 036, 049, 144, 146, 188, 320, 346, 363, 381, 382, 400, 428, 4G8, 487, 507, 509, 530, 531, 534, 575, 603, 663 242, 433, 647, 685 66 1 125 041, 529 058 622 647 640 174 602 387, 437, 459, 675, 683 665 07 1 092, 093, 094, 191, 411, 476 121 093, 593
Shishido, K. Shishido, T. Shitani, R. Shoair, A.G. Shoemaker, H.E. Shook, B.C. Shorokhodov, V.I. Shrma, A.K. Shu, L. Shukla, M.R. Shuzui, I.
StULL
Sidler, D.R. Siebeneicher, H. Siegel, D.R. Siegert, P. Siegfried, S. Sieinsen, P. Signorella, S.
SillLX
Silcoff, E.R. Silina, A. Silva Jr., L. Silva, D.de 0. Silveira, C.C.
Silver, M.E. &Iverman. rt& Silvo, A.R. Sim, K.-Y.
slmd&
Simon, J.
S. Simpson, I.D. S i m y r a . I. Sinbandhit, S. Singh, A. &iyh. .I, Singh, N. Singh, R.P. Singh, S. Singh, V.
450, 567, 588, 670 184,284, 702 201 495 067 439 372 689 351, 353, 354, 360, 625 524 661 691 176, 181 311 259 264 689 186, 226 286 541 215, 231 484 144 324 535 580 641 599 310, 494, 578, 632, 647, 695 512 074 509
249 219,375 073,482 333 612 317, 519, 543 010 172, 270, 288, 297 069 095,399, 686 092 140 613 399, 686
AUTIIOR INDEX
h z h . V.Y,
eton. D A Sinha, J. Sinha, P. Sinha, S. Siniscalchi, F.R. Sinkeldam, R.W. Siquet, C. Sirieix, .1. Sirol, S . Sivakurnar, M. Sivappa, R. Sivasankar, S. Six, C. Sjiiholm, A. Skatteb~l,L. Skidmore, J. Skinner, C.J. Sklenicka, H.M. Skowrofiska, A. Skulski. 1,. Slade, .I. Slavin, .I. Slawin, A.M.Z. Sliveira, C.C. . . ,' Smietana, M. Smil, D.V. Smith, A.C. Smith, A.D. Smith, H.W. Smith, 1. Smith, J.A. Smith, M.B. Smith, M.E. Smith, N.M. Smith, P.M. Smith, R.C. Smith, T A D . Smulik, J.A.
Snow, J.W.
068, 076, 086, 111, 113, 140, 279, 359, 457, 517, 573, 594 072 357, 366 032 123, 509 475 188 059, 128, 130, 464, 650, 657 373 147 057 419 323 698 456 357, 604 103 352, 354 374 167, 606 257 313, 374 083,308 387 349 030 054,061, 472 532, 651 037, 041 480 241, 279, 28 1 218 228 352 065, 373,479 161 376 154 549 078 340 430, 433 266,272, 376, 610, 687, 691 324 232 418
779
Snowden, D.J.
SQaLX
Sodergren, M.J. Sogon, T. Soheili, A. Sohn, S.-M. Sokolowska, J. SOIS, L. Solay, M. Soldevilla, A. Soler, T. Solhy, A. Solin, N. Solis-oba, A. Somers, J.J. Somerville, K.B. Son. S.U. Son, Y.-C. Sonawane, N.D. Sonfai. P. Song, C. Song, C.-S.
Sow. G . Song, Q. song, S.-E. Song, S.-J. song, s.-Y. Song, S.H. Song, X.
SQuX
Song, Z. Song, Z.-L. Soni, P. Sonmor, E.R. Sonobe, II. Sonoda, K. Soufiaoui, M. Souizi. A. Souma, Y. Souadararajan, N. Southern, J.M. Sowa Jr., .I&
a
283 025,032 558 447 577 498 274 029, 118 650 276 27 1 674 583 075 337 186 259 238, 357, 517, 6 14 438, 671, 676, 678, 679, 681, 684 093 603 604 178 390 048, 188, 353, 358 228,-474 451, 491, 683 409 498 224 344 179 204, 267 010 668 415 240 687 184 154, 306, 339, 348 390 573 015 247 701 134
780
Spagnol, M. Spagnolo, P. Sparks, T. Spek, A.L. Snencer. J.B. Spencer, K.L. Sperandio, A.
sl=LnM.
Sperrle, M. Spey, S.E. Spiciaiich, D. W.J. Spina, G. Spoor, P.
bsQuJLX
Sreekanth, A.R. Sreekumar, K. Sridharan, V. Srihaii, P. Srinivas, C. Srinivas, D. Srinivas, G . Srinivas, R. Srinivasan. K.V. Srinivasan, R. Srinivasu, P. Srivastava, S.K. Srividya, R. Sromek, A.W. St. Laurent, D.R St.-Martin, D. Stafford, D.G. StHhelin, C. btalick. W.M. Stambuli, J.P. Stainmers, T. 1
.
Stankovik, S. Staples, R.J. Starikova, Z.A. Stsuffer, S.K. Stavenger, R.A. Stavrescu, R. Steck, P.1,. Ste?ensm,l. R.W,
AUTI-IORINDEX
059,060, 283 572 563 067 570, 577 318 445, 666 288 692 218 297 511 48 1 129 101 677 305 558, 587, 589, 658 034, 363, 573 363 499, 659 2x4 010 078, 106, 111, 424, 601 459 095 084, 373 287 074,088 397,398 61 1 017 441 456 513 094 292 702 039 493, 495 412, 523 519 2x3 292 543 007 574 322
&fane, B. Stefani, H.A. Steffens, M.C. Stegmann, V.R. Stehle, N. Stein, D. Steiner, A.
..
einic&G. Steinmann, J.E. Stelzer, F. Stengel, T. Stenson, R.A. Stent, M.A.H.
Stenzel, W. Stephan, M.L. Stephenson, C.R.J. Stephenson, G.A. Stergiades, I.A. Sterrenburg, J.G. Stetter, J. Stevenazzi, A. Stevens, E.P. Stevenson. P.J, Steward, O.W. Stickney, C.A. Stien, D. Stiff, C.M. Stiriha, S.-E. Stocks, M.J. Stokes, S.S. Storer, R.I. Storey, J.M.D. Stragies, R. Stranne, R. Shatford, P.W. Straub, J.A. gtrauss C R Sheet, L.J. Striickler, R.R. Strukul, G. Stmwe, P. Stilrker. J.M. Stuart, A.M.
Studemann, T.
2sukuL
Studley, J.R. Sturla, S.J.
320 494,599 558 343,391 246 240 350, 352 288,458 482 213 171 234 046 149 512 261,470 214 545 454 635 672 585 300 567 550 330 250 603 282 212 652 69 1 237 269 436 127 03 1 702 020 578 482 376 108 008 412 561 149 081, 178 061, 254, 689 341, 654 437
78 1
AUTHOR INDEX
su, F.-Y. Su, M.
su,
w.
Suh-ez, A.
Su5rez-Sohrino. A.L. Suhha Reddy, B.V. Suhhmaj, K. Subharao, Y .T. Suhhani, S. Suhrahmanyani, M. Suhramanyam, R.V.K.
Suds. K. Suda,
s.
Sudha, K.
wV, Vr.
Suenag, ‘r. Suenaga, Y. Suga, s. Sugae, T.
Sugai, T. Sugano, M. Sugawara, M. Sugawara, s. Sugihara, 11. Surihiira. T. Sugihara, Y. Sugimoto, €1. Sugimotot, K. Surinome. h4. Sugiomoto, T. Sugita, K. Sugiura, M. Sugiyama, E. Sugiyama, S. Sugoh, K. Sugunun, S. Suguro, M. Suh, J.-M. Suhendra, M. Suih. S L. Suk, J.Y. Sukai, A.K.
085, 311 084, 442, 664 023, 277 157 560 672 034, 045, 255, 363, 395, 573, 700 428 323 28 1 620 265 101 267, 506 014, 064, 259, 312, 356, 473, 498, 698 546 436 125 229 124, 235 428, 536 0.56 040, 235 219 089 690 566 591, 676, 688 335 311,323 674 034,173 101 152 346, 406 129, 273,573 267, 292, 682 610 251, 428, 536 305 002, 137, 177 596 306 093 170, 244 106
Sukirthalingm, S. Sumida, N. Sumida, S.-i. Surnitra, G. Sun, Sun, Sun, Sun, Sun,
A,-M. J.
K.-I,. L.
P.-D.
Sun. W.-It Sun, X.
SUlJL Sun. Y.-K. Sunder, K.S. Sundermeier, M. Sundermeier, U. Sung, B.S. Sung, D.W.1,. Sung, H.R. &n. J.J. Sung, M.J. Sung, s.-y. Superchi, S. Suri, K.A. Suriaatmaja, M. Surivet, J.-P. Surva J’rakash. G . L Sutherland. A.J, Suwa, T.
Su\talna T, Suzuki, A. Suzuki, D. Suzuki, 11. m i k i . K.
Suzuki, M. Suzuki, R. Suzuki, S.
589
586 110 442,555 088, 114 297 493 160, 248, 378 267 599 053 155,383, 448 110, 315 134, 641 060 601, 645 405,420 42 1 390,501 682 031 116 613 044 038, 067, 135, 203 024 248 248 495 454, 693 482 448 066, 192, 267, 292, 607, 682 125 320 252, 511, 682 116, 557 472, 477, 491, 693 477 252, 299, 357, 369, 538 207, 278 606 124
782
Suzuki. T.
Suzuki, Y. Svensen, H. Svenstmp, N. Swallow, s. Swatn in a t h ail. S. Swuny, D.N. Swanson, E. Swarbrick, M.E. Swarnalakshmi, S. Sweeney, Z.K. Swiatek, A. Swierczek, K. $w~enogu,0. Syamala, M. Syper, L. Szahb, K.J. Szillot, 11. SzOll6sy, A.
Tahaei, M.1-I. Tahx-Heydar, K Tahar-IIydar, K. laher. r1.T;. Tahuchi, N. Tahussa, F. Tachi, K. Tachiliana, K. Tada, M. Taga, T. Tagarelli, A. Tagut, J.R. ngaya, II.
AUTHOR INDEX
050, 074, 077, 079, 080, 090, 183, 198, 202, 210, 218, 365, 407, 437, 457, 528, 535, 537, 562, 655, 666 135 294 580 570 020, 304, 306, 423 674 344 120 589 018,383 4x5 349 125 597 087 006, 630 016 583 213 104 035, 216, 217, 278, 298, 380, 588
112 097, 101 097, 098, 099 403 546, 673 267 040 343 124, 220, 338, 339 018, 307 590, 619 184, 548 322 317
Taggi, A.E.
Tahir, R. Tahmasehi, D.P. Tai, C.-L. Tai, H.-M. Taiji, T. Tajhakhsh, M. Tajik, H. Takaha, D. Takahe, K. Takada, T. Takagi, ti. Takagi, J.
Takaei..
Takagi, T. Takagi, Y. Takagishi, H. Takahashi, G. Takahashi, K. Takahwhi, M. Takahashi. T.
Takahata, H. Takahisa, E. Takai, Y. Takaki. K. Takami, K. Takunizawa, S. Takanruni, T. Takao, G. Takao, 11. Takasugi, S. Takaya, H. Takaya, J. Takaya, K. Takaya, Y.
256, 262, 624 067 328, 400, 437, 546, 605, 666, 673 674 345 673 253 128, 288 422 100, 107, 108, 112, 415 092 182 656 068 016, 105, 133, 208 656 011,393 223, 223, 671 618 216,451 583 459 335 058 288, 629, 633, 636 119, 167, 168, 239, 325, 383, 426, 438, 448, 483, 636, 693 050, 392 459 218, 442, 553, 652 428,536 184, 284,702 428,446 297 101 334 676 183 152 063,583 569, 607, 608 318 200,201
783
AUTHOR INDEX
Takayama, K. Takayama, Y. Takeda, A. Takeda, A.a. Takerla, H.
Takeda, Y. Takehara, A. Takehira, K. Takei, 1. Takemiya, A. Takemura, S. Takeno, 11. Takeuchi, H. Takeuchi, I(. Takeuchi. B, Takeucht. S, Takeuchi, Y. Takezawa, E. Takezawa, F. Takhi, M. Takimoto, M. Takizawa, S. Takizwa, J.-i. Taktak, S. Takuma, Y. Talawar, M.B. Tallant, M. Tallarico, J.A. Talukdur, S. Talyhov, G.M. Tam, W. Tamakita, H. TamamiB,
Tamamura. H. Tamaoka, Y.
Tamazaki, I. Tamhankar, B.V. Tamm, M. Tan. C.-0. Tan. K.-T. Tan, K.L.
274 553 616 173 621 214, 216, 352, 451, 462, 467, 615, 653 622 127 184, 284, 702
300
361 024, 035, 278, 595 688 516 061, 508, 621 219,590 116, 272 023 364, 570 097 215 082 333, 499 392, 416, 476 5 14 034 297 305 586 376 308, 417, 450, 502 643 435 07 1 046, 110, 305, 346 569 619 033, 037, 041, 406, 505, 556, 563 135 371 489 155 036, 175, 341 272
Tan, R. Tan, Z.
Tao. W.-T.
162 408 272, 414 052, 079, 227, 312, 368, 519, 544, 628 074 251,428, 536 038,391,a 506 190, 297, 486, 539, 672, 684 015, 038, 135, 151, 621, 705, 706,707 506 298 037, 116, 406, 486,505, 563 043, 050, 135, 414,511 127, 129, 369, 66 1 130 050,074 548 379 641 699 660 211, 284, 634 075, 077, 109, 346, 475, 526 380,486 011, 014 430 250 046, 100 435 428 087 702 124,394 598 237 304 627, 628 643 210
Tapolczay, D.J.
701
33nihJL
Tanahashi, C. Tanaka, A.
lkukiia Tanka, J. %aka&
Tanaka, N. Tanaka, R. Tanaka, S. Tanaka. T. Tanaka, Y. Tanaka, Y .-i.
Iiumsmx Tang, H. Tang, T.P. Tang, X.-Q.
Tani, S. Taniguchi, Y. Tanikawa, M. Tanino, K. Tankguchi, M. Tankguchi, N. Tankguchi, T. Tankguchi, Y. Tanko. J.M, Tannai, €1. Tanner, D.
TdO,
B.
784
Tqian-Nasab, A. Taran, I;. Tararov, V.I. Tarhit, B . Tardif, 0. Tamai, T. Tmade, A. Tashiro. Tasinuzo, M. Tasneem Tasneem, Ali M.M. Tatai, J. Tatamidani, H. Tateiwa, J.-i. Tatsukawa, A. Tavakol, H. Tayruna, E. Taylor, A. Taylor, B. Taylor, M. Taylor, N.J.
l3xkLuL
Taylor, R.A. Tavlor. R.E. J’avlor. R.I.K. Taylor, S.J. Tedeschi, L. Tedron, J.S. Tehrani, K.A. Teimouri, M.B. Tejedor, D. Tkjero, T. Temnperini, A. ten Brink, G.-J. ten Hoke, P. Ten, A. Teng, L. Teng, X. Tennyson, R.L. A.V ter Halle, R. Teranishi, I f . T e r m 1. Terao, Y. Teraoka,Y. Terefenko, E.A. Terrano, D. Terstiege, I.
AUTHOR INDEX
477 335 158, 648, 649 140 258, 699 181 067 258, 598 160 649 560 477 194 379 202 076 700 25 1 563 410 302 492 332 193 039, 212 365, 434, 440, 464, 611 518, 521 512 708 4x5 615 4 75 015,388 262 622 330,357 029 06 1 08 1 340, 553 311 058 059,060 244 425 035, 121, 221 244 387 050, 403 427
Terui, H. Testaferri, L. Thadani, A.N. Thakur, A.J. Thakuria, J.A. Thalji, R.K. Thayumanavan, R. Thede, K. Theeraladanon, C. Thevenin, P. ‘hiaw-Woaye, A. Thihonnet, J. ThiCry, V.
Thijs, L. Thirsk, C.
Thissell, J.G. Thogsomkleeb, C. Thomas. A.W. Thomas, C. Thomas, C.B. Thomas, G.11. Thomas, L. Thomas, P.J. Thomas, R.M. Thomas, s. Thomas, S.A. Thomassigny, C. Thomazeau, C. Thompson, N. Thompson, S.P. Thomson, P. Thongchant, S. Thorhauge, J. Thoritnhert, S . Thorpe, T. Thurner, A. Thurston, V.T. Tian, H. Tian, Q. Tian, S.-K. Tian, Y. Tian, S. Tiecco. M. Tijani, J. Tillack, A. Tillement, 0. Tillyer, R.
569 622, 649 037,041,558 262, 423, 441, 448 020 180 182 151 586 151 042 190, 694 369 3 14 022, 029 596 148 08 1 629 096 654 376 132 325 086 288, 297, 662 484 075 061 567 380 563 259 202 236 054 552 652 352, 353, 404 426,435 497, 630 026, 292 284 622, 649 111, 151, 574 633 231, 264, 271, 298, 615 139, 141, 382 577
AUIXOR INDEX
ustarn. IT. Tiimnennann, A. Timmons, D.J. Timofeeva, (3.1. Tino, R. Tinsley, A S . Tippmann, E. Tissandit, S. Tius. M.A. Tivola, P.B. Tjen, K.C.M.F. To, D.C.M. Toader, D. Tohisu, M. Toda, A. To'oda.F, Totla, N. J - ~rr.~ ~ . Tohi, K. Tohma, 1-1. T&e, I.. Tokitoh, N. Tokudda. M. Tokunaga, K. Tokunaga, N. lolhert, L.M. Tolomelli, A. Toma. S. Toma. 3. Tomis, M. Tomatsu, A. Tomimoto, K. Tornioka. K. Tomioka, T. Tomizawa, T. Tommnasino. M.L. Tomooka. K. Tone, €1. Tong, P.-E. Topping, C.M. Tor. Y. Toratsu, C. Torchy, S .
162 178 340 649 702 530 024 148 274 275 545, 589 653 591 645 467, 694 331 590, 619 684 693 235, 239, 374, 518 055, 476, 667 194,552 157, 158 138, 152, 287, 367,447, 495 468 348 090, 613 430 00 1 241, 596 384 291,418 119, 672 688 102, 367 042, 195, 199, 242, 308, 352 381 037 06 1 345 212 196 180 247 218 278
Toni, T. Toriyama, F. Tor6, A. T6rtik.B, Torraca, K.E. Tone, G. Torregiani, E. Tortolani. D.& Tortorella, P.
3hULL
Toste, F.D.
Tbth, J. Tbth, M. Touchlud, F. Touillaux, R. Toupet, L. Tour. J.M. Townsend, R.J. Toyota, S. Tozer, M.J. Trabanco, A.A. Trahocchi, A. Tranchant, I. Tripani, C. Trauthwein, €I. Traverse, J.F. Trecourt, F. Trevisan, R. Trevitt, G.P. Trewhella, M A . Tripathy, S. Trofimenko, S. Trogolo, C.
Troln..
Tromhini. C. Trost. D.M.
Trotman, S. Trotman, S.E. Troupel, M.
785
198, 202 694 467 3 84 336,347 247 210, 368, 604, 681 285 481,482 334, 697 386, 454, 692, 694 304 297 061 450 634 371,473 211, 658 304 673 684 583 218 581, 616 313 283 264, 615 266, 272 139 294 205 054, 061 293 248 212 239 605, 606 023, 519 386, 408, 427, 437, 454, 535, 537, 543, 550, 552, 617, 620, 659, 678, 686, 691, 692, 693, 694 015 036 399
786
Troutman, M.V.
llukmdL
Tsadjout, A. Tsai, F.-Y. Tsai, Y.-C. Tsay, S.-C. Tschaen, D.M.
EiLEL
Tseng, C.-T. Tsuhoya, N. Tsuchimoto, T. Tsuchiya, T. Tsudoda, T. Tsuji, C. IUIiL
Tsujigami, T. Tsujimoto, M. Tsujimoto, S. Tsukagoshi, T. Tsukazaki, M. . . 1, Tsukinoki. Tsunoda. T. Tsuritani, T. Tsutsui, 11. Tsutsumi, K. Tsutsumi, T. Tu, S.-J. Tu, Y.
3hJ.Q.
Tuchiya, Y. Tucker, J.L. Tunoori, A.R. Turet, L. Turner, H.W. Turner, P. Tverewvsky, V.V. 'Ijrkwinski, R.R. Tymonko, S.A. Tyvorskii, V.I. Tzalis, D.
Ilchida, T. Uchiro, H.
AUTHOR INDEX
159 275 085, 575 119, 168 283 536 010 165 205 115 387, 437, 459 404,492 225 515 406, 435 056 062 393 459 687 097 160 656 507,530, 603 167, 174, 263 538 063 043 415, 625 542, 668 215 159,304 098 086 293 360 516 484 392 646 4X7,600
055, 057, 123 126, 213, 214, 217, 218, 219, 527 018,047
Uchiyama, M. Ue, N. Ueha, M. Ueda, H. Ueda, K. Ueda, M. Ueda, N. Uedo, E. Uegaki, M. Uehira, S. Uemura, K.
Uemura, T. Ueno, M. Uenoyama, S.-y. Ujihara, Y. Ukai, K. Ulltich, E.C. Urn, S.Y. Uma, R. Umani, F. IJmani-Ronchi. & IJmedn, S. Uinesha, K.B. Ungureanu, I. ITozumi. Y. Upadhyay, V. Upeandran, B. Uppalla, L.S. Ura, Y. Urabe, H. Urano, J. Urch, C.J. Usher, L.C. LJstvnvuk. N .A . Usugi, S.-i. Usuki, J. Utimoto, K. Uziel, J.
518 272 377,384 292 398 036, 240, 597 388, 569, 571, 592, 635 162, 564 622 530, 531,534 640 091, 094, 097, 208, 300, 315, 390, 392, 409, 414, 491, 505, 686 063 520, 606 344 068 661, 693 508 432 391,537 239 024, 033, 647 023 608 164, 271 238 129 487 083 019, 075, 095, 322,367, 707 636 116, 430, 436, 557,679 611 097 263,302 454, 532 219 138 683 661, 693 104, 473
787
AUTHOR INDEX
056 013 045, 074, 302, 467, 532 465 Vadehra, A. 415 Vaghei, R.G. 602 Vago, M. 392, 521 Vaidvanathan. R. 516 Vaillancourt, L. 359 662 Vairamani, M. 083 Vakalopoulos, A. 552 Valacchi, M. 059 ValidC, B. 502 Valdivia, M.V. 449 Valenciano, J. 339 Valenli. P, 312 Valereu. P. 280, 471, 609 VallCe. Y. 034,081 Valleix, A. 460 Vallin, K.S.A. 076 Valluii, M. 249, 283 Valot, F. 048 Van Bierheek, A. 447 Van Veidhuizen, J.J. 426, 448, 657 Van V r a n k a 050, 051 van Beilen, J.B. 257 vim den I-Ieuvel,M. 564 van den Hoven, B.G. 323, 548 van der Gen, A. 276 van der Sluis, M. 105 van der Veen, L.A. 293 van Es, D.S. van Leeuven. P.W.N.M. 064, 067, 105, 293 453 van Maarseveen, J.H. 248 van Rantwijk, F. 092 van Staden, M. 355, 356, 357, van Vliet. M.C.A. 361, 362 176 van Vrinken. D.L, 454 van Vuuren, E. 378 van Well, R. 452 van Zijl, A.W. 629 Vanddenhossche, C.P. 140 Vanderstraeten, P.E. 292 VanCk, P. 081,327,414 449 307,556 Varchi. G. Varela, J.J. 07 1 v. Keyserlingk, N.G. Vaal, M.J. Vaccaro. L.
Varghese, B. Varghese, J.P. Vasapollo, G. Vasella, T. Vasquez, P.C. Vass. A. Vassiliou, S. Vauthey, I. Vazquez, E. Vbquez, s. V w u e z , V.
yc-dc%L
Veerendhar, G. Velmathi, S. Veltri, L. Velu, s. Velu, S.E. Venkatachalam, C.S. Venkataiah, B. Venkatraman, S. Ventraman, M.S. Venugopal, D. Verbicky, C.A. Verdaguer, X. Vereshchagin, A.N.
Verveer, P.C. Verza, E. VeverkovB, E. Vial, L. Vicart, N. Vice, S.F. Viciu, M.S. Vidal, J.-P. Vidal-Feman, A. Vieira, N.M.L. Vieira, T.O. Viertler, H.
60 1 137 253, 304, 409, 463 636, 639 081 321 393 304 163
045
010, 215 249 422 540 515 246 515 235 383 587 698 571 6 19 313, 418 276, 347 620 144, 150, 203, 204 095 653 620 454 386, 684 525,528 441, 549 081, 087, 324, 342,440,698 247 073 418 184 188 181, 244 289 260 060 533 641 360
788
Vignola, N. Vigo, T.L. Vijayalakshmni, P. Vilaivan. T, w a s a . J, Villani, C. Villar, F. Villiers, P. Vinader, V. Vinatoru, M. Vinod, A.U. Violleau, F. Vis, J.-M. Visser, G.M. Viswanathan, G.S. Viswanathan, R. Vitt, S. Vittal, J.J. Vivelo, J. Vivian, R.W. Vo-Tranh, G. Vogel, R. Vogle, M. VoigtlZnder, D. Voigtmann, U. Volant, F. Volante, R.P. Volkman, S.K. Vorogushin, A. Voronkov, M.G. Voronkov, M.V. Vos, T.J. Voskrcsensky, S . Vrancken, E. Vrieze, K. Vu, A.T. vyils, K.
Wack, H. Wada, K. Wnda. M. Wada, T. Wada, Y. Wadamoto, M. Wadgaonkar, P.P.
AUTHOR INDEX
311 269 230 043 083, 263, 302 208, 466, 617 469, 641 136, 137 188 129 097 677 369 330 247 342, 644 299 319, 329 522 083 542 429 422 141, 147 037, 402, 403 436 07 1 290 699 547 120 598 265 447 282 557 188 120 258
256, 262, 624 344 020, 038, 056 102, 340 298 539 371, 414
Wadsworth, K.J. Wagaw, s. Wager, C.A. Wager, T.T. Wagle, D.R. Wailer, J.S. Wainwright, P.G. Waite, D. Wakahayashi, A. Wakabayashi, H. Wakabayashi, K. Wakamaatsu, H. Wakasa, N. Wakasugi, K. Wakiji, I. Wakita,T. Wakui, II. Wald, S.A. Waldvogel, E. Wallace. D.J. Waller, F.J. Walsh, P.J. Wan, C.-W. Wan, Y. Wan, %. Wang, A.
lYanLJL
Wang, C.-J. W ~ I IC.-L.J. ~, Wang, c.c.-Y
lYmLrL
Wang, D.-K. Wan?. F, Wang, F.-S. Wang, G. Wang, H. Wang, H.-M. Wang, H.-s. Wang, H.F. Wanc. J. Wang, J.-H.
411 296 037, 065, 337,
507
065 161 368 360,363 355,596 087 676 522 179,320, 575 456 297 227, 312 181, 613 374 491,494 208 035, 121 304, 629 151 154 095,479 218 001 098,347 318 168 019, 420, 432, 461 172, 703 258 064, 612
103 204, 626 284 474,668 433 024, 635, 661 023, 118, 168, 193 416 023 177 060, 247, 408, 580 405 655, 666
AUTIlOR INDEX
Wane. J , - x Wang, K. Wang, L.
Wang, L.-C. Wang, L.-X. Wang, M. Wang, M.F. Wang, Q . Wane. R. Wang, R.-B. Wang, R.-M. Wang, S. Wang, S.-K. Wang, T. Wang, W. Wang, X. Wang, X.-C. Wang, X.-h. Wang, X.-R.
xulcL Wane. Y . 4 ; . Wane. Y.-k. Wang, Y.-P. wdIuuu
Wang, Z.-X. Ward, A.D. Ward. D.E. W a Waring, M.J. Waiiier, D.L. WatTen, s. W m i n gton, J .M. Warshakoon, N. Warwel, s. Wassermann, B.C Watahiki, T. Watanabe, 11.
224, 387, 492, 690 492 118 003, 006, 150, 224, 306, 337, 483, 488, 599, 601 221,536 215, 548 407 017 022, 331, 550 022,023, 030 249 363 138, 330 123 389 324,330 375, 432, 595, 694 358 152 023 251, 302, 318, 378, 556, 568, 661, 382 587 39 1 363 004, 005, 061, 156, 166, 186, 252, 342, 426, 440, 507, 665, 695 490 237 549 237 193, 540 038, 458 246 220 46 1 326 362 478 079,080 057, 060, 425, 476
Watruiabe, M. Watanahe, S. Watanabe, T. Watanahe. Y. Watanuki, K. Watanuki, N.
Wataya, Y. Waterlot, c. Waters, M.J. Watkin, J.G. Watson, S.P. Wavmouth. R.M. We, 11.-x. Weacing, R. Weckerle, B . Weerasooriya, N. Wehn, P.M. Wei, B. Wei, 14.-X. Wei, L.-L. Wei, L.-M. Wei, Q. Wei, X. Weigand, B. Weiler, L. Weinherg, W.11. Weininann, H. Weinseimer, D.C. Weisleder, D. Weiss, A.H. Weissman, 11. Weissinan, S.A. Welch, S.L. Welton, T.
J3kukLL Wendling, F.
Wentworth, A.D. Weskarnp, T. Wessjohann, L.A. West. F.G,
789
082 140, 189, 475 190, 335, 407, 677 076,334, 697 339 135 090 606 460 702 038, 458 680, 685 527 680 003 05 1 414 233 387, 492,690 434, 449, 55 1, 554, 559, 565, 574,575, 576 167, 43 1, 488, 489, 504, 521, 538, 545, 606 43 1 635 365, 434,440 111 48 1 293 162 240, 246, 603 541 442 246 179 259 141 161 453, 465, 677, 681, 695 554 468 636 636 448 141 030, 647 178, 187
790
Westman. J. Wettstein, P. Weui, Z.-L. Wever, R. Whisler, M.C. Whithv. R.J, Whitcombe, N.J. White, J.M. White, P.S. Whitehead, A.J. Whittaker, D.T.E. Whittle, A.J. Wiaux, M. Wibbeling, B. Wj!xycD Widehem, R. W i d e n h o m Widhalm. MWiener, J.J.M. Wiese, K.-D. Wiest, O.G. Wiggin, C.J. Wignherg, J.B.P.A. Wijgergans, J.-P. Wilh, N. Wilcoxen, K. Wiliams, J.M.J. Wilkinson, D.E. Wilkinson, H.S. Willems, M. William, A.D. Williams, D.A.J. Williams. D.B.G. Williams, I.D. Williams, M.R.V. Williamson, J.S. Willis, D.M. Willis, S. Wilson, D. Wilson, F.X. Wilson, P.D. Wink, D. Winn, C.L. Winotapan, C. Winsel, 1-1. Winsor. D.L.
AUTHOR INDEX
446 513 055 064 516 690 467 098 441, 520 333, 340 596 152, 575 402, 481 086 551 661 082 072, 177, 432, 465, 466, 667 028 561 104 621 093, 390 064 029 216 189 176 013 304, 629 171 706 578 323 49 1 054, 130- 418, 466 257 297 376 620, 628 449,559 589 046 118 069 196 043 573 269
Winum, J.-Y.
JYw-E
Wirschun, W.G.
lKiKLL
Wisnoski, D.D. Witholt, B. Witsil, D.R. Wittenherger, S.J.
Wlodarczak, L. Wojcik, J.M. W6jtowicz, H. Wolf, L.B. Wolfe, J.P. Wolfson, A. Wolter, M. Won, H.S. Wong, K.-Y. Wong, K.-y.
YhxhuuL Worden, S. Worrell, J.H.
Wright, D.M.J. Wright, P.T. Wu, A. Wu, B. w u , C.-w. Wu, H.
KLL
WU, J.-D. Wu, J.X. wu, L.-L. WU.M.-.I. WU, M.-S. Wu, M.H. w u , P. WU, Q.-Q.
wu, s.
WU, T.-F. wu. w. w u , x. mlJhA
MLX&
wu. Y.-L.
263 045, 375, 470 610 621 626 050, 051 094 210 171, 488 375 422 011 59 1 291, 294, 646 569 2.54 432 20 1 030, 349 350, 626 222 062, 198 382 279 454,464, 532 256 583 483 132 041 311, 706 053, 163, 239, 273, 302, 602 673 367 364 431 117 530 580 416 634, 639 053 364 251,371 013 027,529 166, 241,529
AUTIIOR INDEX
wu. 2. Wuchrer, M. Wulff, c.
3YJma.L
Buts. P . G N
Wynn, T. Wynne, J.11. wyss, C.
xi, c. xiz
Xia, C. Xia, L.-J. Xia, M. Xia, W. Xia, W.-J. Xiang, B. Xiang, C.-L Xiao. D.
Xiao, W. Xiao, w.-J. Xiao, x. Xie, I). Xie, €1.
xi.dL
.
-,
Xie, R.L. Xie, X. Xin. X.-0. Xin, Z.-Q. Xiong, z . - x . xu, G.
u
x u , .I.-11. Xu, K.-C. x u , L. Xu, M.-I-I.
u
Xu, Q.-h. xu, x .
035, 036, 124, 368, 369, 468, 662 454,537 111 597 012 069 023 004 513
483, 636, 693 438, 491, 683 404 330 185, 225, 394 494, 634 668 456 036 159, 191, 278, 594 131, 140, 410, 561 266 631, 636, 639 504, 506 180, 650 635 530 056 649 588 392 022 637 004, 665 040, 352, 699 053 522 131, 410 324, 330 015, 023, 024, 705 020, 311, 423 449
791
xu, X.-H.
XU, Y.-M. Xuan, J.X. Xue, s. Y a k , M. Yahu, M. Yadav, J.C. Yadav. J.S.
K
Yadollahi, 13. Yakahe, S.
Yakatsuki, H. Yakeda, A. Yakemoto, T. Yakura, T. Yamada, K. Yanada, K.-i. Yamada, M. Yuiiada, N. Yamada. T. Yrunada, Y.M.A. Yunacloi, S. Yanaga, T. Yiunagiwa, N. Yamaguchi, K.
Yamamchi. M.
364 578 205 597 673 032 069 047 034, 045, 055, 074, 078, 082, 083, 087, 088, 106, 107, 109, 111, 112, 114, 130, 206, 209, 231, 235, 255, 270, 275, 280, 301, 302, 303, 305, 342, 363, 395, 417, 418, 424, 440, 499, 524, 525, 573, 584, 601, 605, 614, 615, 641, 659, 700, 701 077,652 075, 077, 109, 475 066, 094, 160, 412 626 115 092 468 312 042, 704 251, 688 468 047, 193, 213, 357, 391, 506, 535,552 544
406 191 537 320 350, 362, 492, 537 003, 261, 591, 631, 670, 687, 688 122
AUTHOR INDEX
792
Yamaguchi, Y.
xiuLiiL
Yrunakawa, K. Yamakawa, T. Yamamoto, A. Yamamoto, C.
Yarnornoto, I. .
,
Y amamoto, N. Yamamoto, S.
Yamamura, H. Yamanaka, H. Yamanaka, M. Yamanaka, R. Yamanashi, M. Yamane, M. Yamasaki, A. Yamasaki, S. Yamasaki, Y. Yamashita, A. Yamashita, €1. Yamashita, K. Yamashila, Y. Yamatake, T. Yamauchi, Y. Yamazaki, A.
207, 328 011, 123 268, 597 122 034, 124 502 021, 029, 039, 041, 082, 101, 122, 124, 189, 227, 273, 283, 353, 407, 439, 520, 528, 529, 536, 537, 539, 544 131 563 125 252, 639, 654, 682 476 064, 069, 101, 115, 117, 118, 119, 121, 146, 169, 172, 173, 198, 225, 242, 284, 393, 394, 428, 436, 437, 447, 455,500, 502, 510, 559, 583, 586, 609, 616, 619, 641, 644, 650, 652, 653, 683, 694 032, 506, 538 430 616 059 494 67G 346,364 071, 533, 607 595, 660 61 1 702 272, 671 125, 126, 128, 412, 569 520, 522 514 562 483
Yamazaki, N. Yaniuaki, S. Yampolsky, I.V. Yan, M. Yan, Q. Yan, S . Yan, Y.-L. Yanagi, T. Yanagihara, R. Yanagisawa, A. Yanagisawa,
M.
Yanamoto, Y. Yang, B. Yang, B .IX Yang, B.Q. Yang, C. Yang, C.X.
xiuuLQYang, D.-H. Yang, D.-Y. Yang, F. Yang, G.-s. ~ a n g r1. , Yang, H.-C. Yang, J. Yang, J.-D. Yang, J.-Y. Yang, K. Yang, L. Yang, L.-w. Yang, M.
xuLLs. Yang, S.-M. Yang, S.H.
b. T.-K,
Yang, T.-k. Yang, W.K. Yang, X. Yang, X.-F. Yang, X.-L. Yang, X.-w. Yang, Y.
234 011,402 5 29 269, 270 198, 20,423 107 224 382 375 035, 278 061 497 021, 029, 407, 537,539 094 634 623 252,317 245, 296 166 177,455 019 103, 350, 358, 375, 626 414 666 485 162 261 311 268, 342, 644 705 036 004, 156, 695 030, 254 201 595 224 283 551 006,423 056, 061, 062, 200,530 023 026,027 030 642 043 023 039, 040, 244, 250,387
AUTHOR INDEX
Yane. -L Yang, Z . - H Yanigisawa, K. Yano, S. Yao. C.-F. Yao, 11. Yao, J. Yao, M.-L.
Yao.O.
x.
Yao, Yap, G.P.A. Yasuka, s. Yashkina, L.V. Yasin, S.A.
Yasuda, K. Yasuda, M. Yasuda, N. Yasuda, T. &&pI--&
Yasuhwa, T. Yasutake, M. Yato, M. Yau, M.
&Y
Yavari, I. Ye, s. Ye, X.-R. Yce, N.K.
ELI& Yeung, C.W. Yeung, Y.-Y. Yin, J . Yin, Y. Yin, Z. Ying, J. Yli-Kauhaluonia. J.
xulL&
Yokie, I. Yokoe, I. Yokota, T. Yokota, W. Yokoyama, 0. Yokoyama, M. Yokoyama, T.
084, 631, 656 548 296 348 221, 222, 441 358 170 186 453, 463 213, 214 461, 483 486 649 59 1 05 6 092 090, 156, 377, 409, 504, 547, 704 299 435 086 308 192 344 243 439 505 211, 634 392 613 128 497 062 44 1 001 005, 143, 254 2 0 , 224 029 171 467 068 346 406 3x3 450 45 7 239, 374 703 232, 429
793
Yoneda, E.
Yoneoka, A. Yong, K.H. XOO.B.-W, Yoo, B.R. Yoo, H.S. Yoo, M.-S. YOO,M.-S. Yoon, C.-O.M.
Yoon, C.H.
hon.
csd,
Yoon, J.-Y. Yoon, N.S. Yoon, S . - K . Yoon, T.P. Yoon, Y.-A. Yoon. Y.-J. Yoon, Y.A. Yorimitsu, 11.
Yorimitsu, S. Yoromitsu, 13. Yoshida, H. Yoshida, K. Yoshida. M. Yoshida, Y. Yoshifuji, M. Yoshikawa, E. Yoshikawa, N. Yoshimoto, K. Yoshimnura, N. Yoshimura, S. Yoshino, M. Yoshino, Y. Yoshioka. N. Yoshizawa, K. You, 1.1.-w.
629, 633, 636 368, 370 538
099
122 007, 277, 400, 451, 668 135 459 597 595 063, 277, 381, 599 306, 698 063, 118, 277, 296, 305, 381, 400,599 444,477 170 002 568, 572 054 043, 228 67 1 179, 188, 320, 363, 381, 382, 428, 446, 511, 575, 663 274 138 683 124, 142, 180, 219, 235, 271 185, 678 250, 655, 674 052,368, 544 298, 654 146, 169, 172 502,535,544 002, 645 079,539 032, 504, 593, 641 634 607 476 391 008, 063, 268, 597 684 366
AUTHOR INDEX
794
YOU,J.-S. You, s.-L. Youn, S.W. Youn, W. Young, B. Young, D.G.J. Youshko, M.I. Yranzo, G.I. Ysuznki, H. Yu, B.M. Yu, c . Yu, C-L.
Yu.c.-w Yu, c . - w .
xu&
YU, r-1. Yu, H.-B. Yu, J. Yu, J.-q. Yu, M. Yu, s. Yu, w .
Yu. W.-Y.
Yu, X.-Q. Yu, Y. Yu, z . Yuan, €1. Yuanyin, C. Yudin, A.K. Yue, D. Yuen, W.-H. Yueng, C.H. Yun, C.-S. Yun, €1. Yun, I. yus. M.
Yusa, Y.
Zahjek, A. Zahn, S.K. 7.aidlewicz. M,
021, 025, 027, 549 405 557 697 262 180 657 248 468 160 353 234, 305, 585 283 559, 584 626 37 1 019, 169, 353 042,070 224, 338 570 505 487, 597 084, 406, 442, 664, 666 255, 349, 668 255 379,494 081, 179, 634 212 419 360 430 626 053 513 027, 596 176, 177 034, 036, 046, 151, 185, 206, 236, 271, 319, 496, 507, 508, 59 1 034
Zakharov, V.I. Zali-Boinee, H. Ziunan, S. Zanardi, F. Zanardi, J. Zanatta, N.
014 299 175
zlhud.
556
Zang, H.-J. Zanka. A. Timotti-Gerosla. A, Zapf, A. Zaporowski, L.F. Zappia, G. Zara, C.L.
-
Zarei, M. Zaworotko, M.J.
Ebajadian, M.H. 7.ecchi. G . Zecri, F.J. Zee, O.P. Zefirov, N.S. Zeg10cka, 0.
Zeitler, K. Zekri, N. Zeng, L. ihli&
zcKlKus
Zerth, H.M. Zetina-Rocha, C. Zeto, c.-P. Zewge, D. Zeynizadeh, B. Zhan, Z.-P. Zhang, A.
zhwL
Zhmg, D. Zhang, F.-Y. Zhang, G. G.-S, Zhang, H. Zhang, 11.-C.
700 596 612 547 339 297 066 442 044,373 058 142, 187,421 686, 694 233 377 444 700 698 562 166 306 443 587 495 283 230 668 083 27 1 494, 495, 695 454, 519, 578, 626, 662 078 204 534 290 048,088, 424 433 421, 494 103, 191, 294, 358 107, 254 157, 667 440,589 313,314, 414 116, 164, 168, 474 117,065 056, 137, 210, 411, 470, 476, 635
AUTHOR INDEX
Zhang, L. Zhang, L.-C. Zhang, M. zllalGx
ZiluLE
Zhang, P.-F. Dane. Q Zhang, R . Zhang, S. Zhang, S.-W.
Zhang, W.-C. & m e . X.
Zhang, X.-X. Zhang, X.L.
i2mLY-
Zhang, %.-II. Zhao, B.T. Zhao, C. Zhao, C.-G. Zhao, C.-Q. Zhao, C.-X.
zbiua'
Zhao, 11. Zhao, J. Zhao. M, Zhao, P. Zhao, Y.-W. Zheng, J. Zheng, T.-C. Zheng, W.-X. Zheng, X. Zheng, X.-Q. Zheng, Y. Zheng, Y . 3 .
170, 599 022 311 132 387 167 411,434,631 349 256, 407, 411, 638 629, 633, 636 504 211, 215, 324, 592 039,527, 663 159, 177, 201, 255, 278, 333, 431, 432, 461, 500, 696 29 1 222 038, 118, 181, 269, 277, 306, 333, 334, 348, 379, 385, 422, 449, 470, 505, 517, 537, 542, 592, 706 159, 191, 311, 317 OX8 025 061, 318 545 705, 707 518,519 023, 162, 485 390 507 010 447 39 1 057 328 624 155, 511 474 038,088 350 213, 214, 217
Zhong, G. Zhong, M.
u zhQuLL
ZhoIlg, Y.-L. Zhou, H. Zhou, 1i.-B.
zlmLL
Zhou, J.-R. Zhou, L.
zhuu. 0 . L
Zhou, S.-m. Zhou, T. Zhou, X. Zhou, X.-G. Zhou, Y. Zhou, Y.-G. Zhou, Y.-M. Zhou, z . Zhou, Z.-H. Zhou, Z.-Y.
ZbLHL Zhu, J.
i&L!L
Zhu, N.-Y. Zhu, S . Zhu, T.-S. Zhu, X.-Z. Zhu, Y. Zhu, Y.-F. Zhuang, W. Zhun, I.V. Zificsak, C.A. Zim, D. Zinunerman, K. Zinn, F.K. Zolfigol, M.A.
zou, G. Zucchi, C. Zueva, L.D. Zuing", F.L. zuo, G.-Y. Zuxing, C.
795
604 271 637, 661, 706, 707 216 683 045,530 056 068 026, 028, 029 306, 3 11, 542, 690 215,548 187 482 088 255 027 284 392 485 548 053,056, 198 025 073 156 375 179,499 053 405 625 189 197, 531, 565 270, 283 488, 489 134, 143 495 393 205 093, 111, 166, 168, 191, 230, 282, 473, 474, 476,477, 479 139
OM)
261 572 025 095 022,029 603, 265
