Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
Compendium of Organic Synthetic Methods
Compendium of Organic Synthetic Methods Volume 9 MICHAEL
B. SMITH
DEPARTMENT OF CHEMISTRY THE UNIVERSITY OF CONNECTICUT STORRS, CONNECTICUT
A Wiley-Interscience
Publication
JOHN WILEY & SONS, INC. New York
l
Chichester
l
Weinheim
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Brisbane
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Sinaar>ore
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Toronto
Copyright 2001 by John Wiley and Sons, Inc., New York. All rights reserved. No part of this publication may be reproduced, stored in a retrieval system or transmitted in any form or by any means, electronic or mechanical, including uploading, downloading, printing, decompiling, recording or otherwise, except as permitted under Sections 107 or 108 of the 1976 United States Copyright Act, without the prior written permission of the Publisher. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 605 Third Avenue, New York, NY 10158-0012, (212) 850-6011, fax (212) 850-6008, E-Mail: PERMREQ @ WILEY.COM. This publication is designed to provide accurate and authoritative information in regard to the subject matter covered. It is sold with the understanding that the publisher is not engaged in rendering professional services. If professional advice or other expert assistance is required, the services of a competent professional person should be sought. ISBN 0-471-22822-2. This title is also available in print as ISBN 0-471-14579-3. For more information about Wiley products, visit our web site at www.Wiley.com.
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
CONTENTS PREFACE ABBREVIATIONS INDEX, MONOFUNCTIONAL COMPOUNDS INDEX, DIFUNCTIONAL COMPOUNDS INTRODUCTION PREPARATION OF ALKYNES PREPARATION OF ACID DERIVATIVES PREPARATION OF ALCOHOLS PREPARATON OF ALDEHYDES PREPARATION OF ALKYLS, METHYLENES AND ARYLS PREPARATION OF AMIDES PREPARATION OF AMINES PREPARATION OF ESTERS PREPARATION OF ETHERS, EPOXIDES AND THIOETHERS 10 PREPARATION OF HALIDES AND SULFONATES 11 PREPARATION OF HYDRIDES 12 PREPARATION OF KETONES 13 PREPARATION OF NITRILES 14 PREPARATION OF ALKENES 15 PREPARATION OF OXIDES 16 PREPARATION OF DIFUNCTIONAL COMPOUNDS AUTHOR INDEX
vii ix ... XIII
xv
1 5 11 48 58 100 117 140 156 171 176 183 208 212 227 235 391
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 Iiterrature of Organic Chemistry. In Volume 2, difunctional compounds were added and this compilation was continued by Louis Hegedus and Leroy Wade for Voume 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). 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 body of 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 9 contains both functional group transformations and carbon-carbon bond forming reactions from the literature appearing in the years 1993, 1994 and 1995. The classification schemes used for volumes 6-8 have been continued. Difunctional compounds appear in Chapter 16. The experienced user of the Compendium will require no special insructions for the use of Volume 9. Author citations and the Author Index have been continued as in Volumes 6-8. 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 througout my writing career, I thank my wife Sarah and my son Steven who have shown unfailing patience and devotion during this work. I also thank Darla Henderson, the editor of this volume. Michael
B. Smith
Department of Chemistry University of Connecticut 55 N. Eagleville Road Storrs, Connecticut 06269-3060 Voice phone: (860)-486-2881 Fax: (860)-486-2981 Email: smith @Inucleus.chem.unconn.edu
vii
ABBREVIATIONS 0 AC
Acetyl
acac AIBN aq*
Acetylacetonate azo-bis-isobutyronitrile Aqueous
&
/
CH3
9-Borabicyclo[3.3.1]nonylboryl
B\9
9-BBN BER BINAP Bn Bz
9-Borabicyclo[3.3.1]nonane Borohydride exchange resin 2R,3S-2,2’-bis-(diphenylphosphino)-1,lr-binapthyl benzyl benzoyl
BOC
t-Butoxycarbonyl
0
&
Ot-Bu
Bu CAM CAN ccat.
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-2-01 1$Cyclooctadienyl 1,3,5cyclooctatrienyl Cyclopentadienyl Camphorsulfonic acid Cl&I33NMe3+Brcetyltrimethylammonium bromide
bPY WPY)
CY (+jH OC DABCO dba DBE DBN DBU DCC
11)
Cyclohexyl Temperature in Degrees Centigrade 1,4-Diazobicyclo[2.2.2]octane dibenzylidene acetone 1,2-Dibromoethane 1,8-Diazabicyclo[5.4.0]undec-7-ene 1,5-Diazabicyclo[4,3,O]non-5-ene 1,3-Dicyclohexylcarbodiimide
-CH2CH2CH2CH3 (NH)2Ce(NO3)6 0 &
OCH2Ph
+o
BrCH2CH2Br
c-C6H13-N=C=N-c-C6H13 ix
X
DCE
ABBREVIATIONS
% de DEA DEAD Dibal-H Diphos (dppe) Diphos-4 (dppb) DMAP DMA DME
1,2-Dichloroethane 2, 3-Dichloro-5,6-dicyano1,4-benzoquinone % Diasteromeric excess Diethylamine Diethylazodicarboxylate Diisobutylaluminum hydride 1,2-bis-(Diphenylphosphino)ethane 1,4-his-(Diphenylphosphino)butane 4-Dimethylaminopyridine Dimethylacetamide Dimethoxyethane
DMF
N,N’-Dimethylformamide
DDQ
C1CH2CH2Cl
HN(CH2CH3)2 Et02C-N=NC02Et (Me2CHCH2)2AlH Ph2PCH2CH2PPh2 Ph2P(CH2)4PPh2
MeOCH2CH20Me 0 H
dmp dpm dPPb dPPe dPPf dPPP dvb e% ee EE Et EDA EDTA FMN fod FP FVP h hv 1,5-HD HMPA HMPT iPr LICA (LIPCA) LDA LHMDS LTMP MABR MAD mCPBA Me MEM Mes
K N(CH3)2
bis-[ 1,3-Di@-methoxyphenyl)1,3-propanedionato] dipivaloylmethanato 1,4-bis-(Diphenylphosphino)butane Ph2P(CH2)4PPh2 1,2-bis-(Diphenylphosphino)ethane Ph2PCH2CH2PPh2 bis-(Diphenylphosphino)ferrocene 1,3-bis-(Diphenylphosphino)propane Ph2P(CH2)3PPh2 Divinylbenzene Electrolysis % Enantiomeric excess EtO(Me)HCO1-Ethoxyethyl -CH2CH3 Ethyl H2NCH2CH2NH2 Ethylenediamine Ethylenediaminetetraacetic acid Flavin mononucleotide tris-(6,6,7,7,8,8,8)-Heptafluoro-2,2-dimethyl-3,5-octanedionate Cyclopentadienyl-bis-carbonyl iron Flash Vacuum Pyrolysis hour (hours) Irradiation with light 1&Hexadienyl (Me3N)3P=O Hexamethylphosphoramide Hexamethylphosphorous triamide (Me3N)3P Isopropyl -CH(CH3)2 Lithium cyclohexylisopropylamide LiN(iPr)2 Lithium diisopropylamide LiN(SiMe3)2 Lithium hexamethyl disilazide Lithium 2,2,6,6-tetramethylpiperidide Methylaluminum bis-(4-bromo-2,6-di-tert-butylphenoxide) bis-(2,6-di-t-butyl-4-methylphenoxy)methyl aluminum meta-Chloroperoxybenzoic acid Methyl -CH3 MeOCH2CH20CH2P-Methoxyethoxymethyl 2,4,6-tri-Me-C6H2 Mesityl
ABBREVIATIONS
MeOCH2CH3SO2-
MOM MS MS MTM NAD NADP Napth NBD NBS NCS NIS Ni(R) NMP Oxone
Methoxymethyl Methanesulfonyl Molecular Sieves (3Aor 483 Methylthiomethyl Nicotinamide adenine dinucleotide Sodium triphosphopyridine nucleotide Napthy CC1oH$ Norbornadiene N-Bromosuccinimide N-Chlorosuccinimide N-Iodosuccinimide Raney nickel N-Methyl-2-pyrrolidinone 2 KHS05.KHS04aK2S04
0P
Polymeric backbone
PCC PDC PEG
Pyridinium chlorochromate Pyridinium dichromate Polyethylene glycol
Ph
Phenyl
PhH PhMe Phth pit
Benzene Toluene Phthaloyl 2-Pyridinecarboxylate
Pip
Piperidine
PMP
4-methoxyphenyl
Pr
n-Propyl
-CH2CH2CH3
PY
Pyridine
N- \ / 3
quant. Red-Al sBu sBuLi Siamyl TADDOI TASF TBAF TBDMS TBHP (t-BuOOH) t-Bu TEBA TEMPO
Quantitative yield [(MeOCH2CH20)2AlH2]Na set-Butyl set-Butyllithium Diisoamyl a,a,a’,a’-tetraaryl-4,5-dimethoxy-1,3-dioxolane tris-(Diethylamino)sulfonium difluorotrimethyl Tetrabutylammonium fluoride t-Butyldimethylsilyl t-Butylhydroperoxide tert-B utyl Triethylbenzylammonium Tetramethylpiperdinyloxy free radical
J
CH3SCH2-
to\/ H-N
3
CH3CH2CH(CH3) CH3CH2CH(Li)CH3 (CH3)2CHCH(CH3)silicate n-Bu4N+F t-BuMe2Si Me3COOH -C(CH3)3 Bn(CH3)3N+
ABBREVIATIONS
xii
TFA TFAA Tf (OTf) THF THP TMEDA TMG TMS TMP TPAP To1 Tr TRIS Ts(Tos)
Trifluoroacetic acid Trifluoroacetic anhydride Triflate Tetrahydrofuran Tetrahydropyran Tetramethylethylenediamine 1,1,3,3-Tetramethylguanidine Trimethylsilyl 2,2,6,6-Tetramethylpiperidine tetra-n-Propylammonium perruthenate Tolyl Trityl Triisopropylphenylsulfonyl Tosyl = p-Toluenesulfonyl
N),,)
Sonication
xc
Chiral auxiliary
CF3COOH (CF3CO)20 -S02CF3(-OS02CF3)
Me2NCH2CH2NMe2 -Si(CH3)3
4-c#&H3 -CPh3 4-Mec6&
INDEX,
MONOFUNCTIONAL
COMPOUNDS
Sections--heavy type Pages--light type Blanks in the table correspond to sections for which no additional examples were found in the literature
Sect. Carboxylic Alcohols, Aldehydes
acids phenols
AmideS AIIli~S
Ketones
PREPARATION
Pg.
30A 45A 60A 90A 105A 180A
9 f: 115 137 206
OF ‘l
7
FROM
Alkynes
Catboxylic derivatives Alcohols,
1 1
acid phenols
31 11
Aldehydes Alkyls, methylenes, aryls Amid=
17 5
18 6
19 6
32 11
33 12
34 13
47 48
48 48
49 49
Ethers, epxoides Halides,
63
64
65
60
60
61
76 loo
77 100
106 140
107 140
121 156 137 171
166 183
167 184
Nitriles Alkenes Miscellaneous
78 101
80 102
52 51
98 129
99 129
113 146
114 148
109 144
111 145
123 156
124 158
128 159 140 172
184 208 199 217
1% 212
197 216
198 217
211 227
212 227
213 227
171 191
172 192
186 209 200 219
201 220
ml 178 173 193
12 3
14 3
15 3
25 7
27 8
29 8
30 9
44 39
45 41
40 29
41 30
55 52 70 65
129 160
159 179 174 193
188 209
71 70
203 220
204 221
217 228
218 228
219 228
59 54
70 55
87888990 112 113
113
113
103 132
104 132
105 133
118 153
72 71
101
130
131
102 131
116 150
117 151
115 149 130 161
131 161
132 161
145 173
146 173
147 174
160 179 175 195
162 181 176 1%
119 154 134 162 149 175
163 182
177 198
179 202
222 232
135 169 150 175
180 204 1% 211
207 223 221 232
120 154
165 182
192 210
20s 221 220 232
43 39 58 53
loo
1% 209
202 220
42 30 57 53
85 111
142 172 157 177
170 191
69 65
97 120
108 142
la3 208
54 52
83 110
96 119
169 189
53 51
82 108
94 118
168 186
39 26
81 102
93 117
138 171
24 7
38 26
68 64
153 176
(RH) Ketones
50 50
61
sulfonates
Hydrides
36 25
58
Amines Esters
23 7
10 2
223 233
209 223
210 225
234 233
225 233
*.. XIII
INDEX, Sections-heavy
DIFUNCTIONAL
COMPOUNDS
type
Pages-light type
Blanks in the table correspond to sections for which no additional examples wem found in the literature
305 337
316 242
326 252
335 283
343 288
307 238
318 243
328 261
337 284
345 290
309 239
320 244
310 239
L
311 239 378
xiv
322 244
352 309
358 325
363 340
359
364
330 267
347 293
354 312
340 330
365 344
331 274
348 296
355 315
361 334
366 350
332 276
341 284
349 296
356
362
367
380
381
382
383
384
385
368
386
INTRODUCTION Relationship between Volume 9 and Previous Volumes. Compendium of Organic Synthetic Methods, Volume 9 presents about 1200 examples of published reactions for the preparation of monofunctional compounds, updating the 10650 in Volumes l-8. Volume 9 contains about 800 examples of reactions which prepare of difunctional compounds with various functional groups. Reviews have long been a feature of this series and Volume 9 adds almost 90 pertinent reviews in the various sections. Volume 9 contains approximately 1000 fewer entries than Volume 8 for an identical three-year period, primarily for difunctional compunds. Interestingly, there are about 500 fewer citations from the most cited journal (Tetrahedron Letters) than in the previous edition. Whether this represents a trend in the literature or an inadvertent selectivity on my part is unknown, but there has been a clear increase in biochemical and total synthesis papers which may account for this. Chapters l-l 4 continue as in Volumes l-8, as does Chapter 15, introduced in Volume 6. Difunctional compounds appear in Chapter 16, as in Volumes 6 and 7. The sections on oxides as part of difunctional compounds, introduced in Volume 7, continues in Chapter 16 of Volumes 8 and 9 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 principle author is indicated by underlining (i.e., Kwon, T.W.; Smith, M. B.), as in Volumes 7 and 8. 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 ascending order of year cited (1993-1995), 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 PhCOOH, and PhCH=CHCH20H t-BuCOOH, PhCH20H PhCH=CHCOOH would all be considered as preparations of carboxylic acids from alcohols. Conjugate reduction and alkylation of unsaturated xv
xvi
INTRODUCTION
ketones, aldehydes, esters, acids, and nitriles have been placed in Sections 740 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 - RCH2COOH (carboxylic acids from hydrides), RMe - RCOOH (carboxylic acids from alkyls), RPh - RCOOH (carboxylic acids from aryls). Note the distinction between R2CO - 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). The following examples illustrate the classfication of some potentially confusing cases: RCH=CHCOOH RCH=CH2 ArH ArH RCHO RCH=CHCHO RCHO R2CH2 RCH2COR RCH=CH2
- RCH=CH2 - RCH=CHCOOH - ArCOOH - ArOAc - RH - RCH=CH2 - RCH3 - R2C0 - R2CHCOR - RCH2CH3
RBr + HC-CH
-
RCH-CR
ROH + RCOOH
-
RCOOR
RCH=CHCHO
-
RCH2CH2CH0
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) Alkynes from halides; also al kynes from al kynes Esters from alcohols; also esters from carboxylic acids Alkyls from alkenes (Conjugate Reduction) Alkyls from alkenes (Conjugate Rduction)
How to Use the Book to Locate Examples of the Preparation of Protection Examples of the preparation of one funcof Monofunctional Compounds. tional group from another are found in the monofunctional index on p. x, 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 alkynes that form new alkynes; Section 16 gives reactions of alkynes that form carboxylic acids; and Section 31 gives reactions of alkynes 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 alkynes from alkynes; carboxylic acids from carboxylic acids; and
INTRODUCTION
xvii
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 frorm Ketones). The aldol condensation can be found in the chapters on difunctional compounds in Section 324 (Alcohol, Thiol-Aldehyde) and in Section 330 (Alcohol, Thiol-Ketone). Examples of the protection of alkynes, carboxylic acids, alcohols, phenols, aldehydes, amides, amines, esters, ketones, and alkenes are also indexed on p. xvii. Section (designated with an A: 15A, 30A, etc.) with “protecting group: reactions 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 Compounds.
and Organization
of Reactions
Forming
Difunctional
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, nitrile, and alkene. Reactions that form difunctional compounds are classified into sections on the basis of two functional grups 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 1,4amino-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 (Ketone-Oxide). Conversion of an oxide to another functional grup is generally found in the “Miscellaneous” section of the sections concerning monofunctional com-
.. . XVIII
INTRODUCTION
pounds. 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: Difunctionaf Product RGC-C-CR RCH(OH)COOH RCH=CHOMe RCHF2 RCH(Br)CHzF RCH(OAc)CH20H RCH(OH)COzMe RCH=CHCH2C02Me RCH=CHOAc RCH(OMe)CH2SO2CH$H2OH RS02CH2CH20H
Section Et/e Alkyne-Alkyne Carboxylic acid-Alcohol Ether-Alkene Halide-Halide Halide-Halide Alcohol-Ester Alcohol-Ester Ester-Alkene Ester-Alkene Alcohol-Ether Alcohol-Oxide
How to Use the Book to Locate Examples of the Preparation of Difunctional Compounds. The difunctional index on pWxi gives the section and page corresponding to each difunctional product. Thus Section 327 (Alcohol, ThiolEster) 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 carcompounds) or boxylic acids from halides (Section 25, monofunctional 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 compund. Such methods are difficult to categorize and may be found in either the monofunctional or 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
INTRODUCTION
xix
RCH(OAc)CH20Ac (ester-ester) would thus be of interest to anyone preparing the diol RCH(OH)CH20H (alcohol-alcohol). Sources of Literature Citations. I thought it would be useful for a reader of this Compendium to see the distribution of citations used to this book (i.e., which journals have the most new synthetic methodology). As seen in the accompanying graph, Tetrahedron Letters and Journal of Organic Chemistry account for roughly 60% of all the citations in Volume 9. This book was not edited to favor one journal, category or type of article over another. Undoubtedly, my own personal preferences are part of the selection but I believe that this compilation is an accurate represention 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 “18 other journals” includes: Accts. Chem. Res.; Acta Chem. Stand.; Angew. Chem. Int. Ed. Engl.; Bull. Chim. Sot. Be/g.; Bull. Chim. Sot. Fr.; Can. J. Chem.; Chem. Ber.; Gazz. Chim. Ital.; Heterocycles; J. Chem. Sot.; J. Het. Chem.; J. Indian Chem. Sot; Liebigs Ann. Chem.; Org. Prep. Proceed Int.; Reel. Tram. Chim., Pays-Bas; and Tetrahedron Asymmetry. In addition, nine more journals were examined but no references were recorded.
18 other journals
KS Perkin I
Tetrahedron
Bull Chem Sot Jpn
Synthesis
JACS
Synth Commun
JCS, Chem Comm
Chem Lett
SynLett
J. Org. Chem.
Tetr. Lett.
Citations
xx INTRODUCTION
Compendium of Organic Synthetic Methods
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
CHAPTER
1
PREPARATION
SECTION
OF ALKYNES
1: ALKYNES
FROM
ALKYNES
Me2CHCH21,
THF
--------SiMePhz
t ;SiMePh,
SmIzSm
80% Murakami.
M,; Hayashi, M.; Ito. YJynlett,
1994,
179 Ph
(CH2)40AC
Ph
Ph , toluene
5% MO(C0)6 , llO°C , 2o”c 4-chlorophenol
AcO(H2C)4
Kaneta, N.; Hikichi,
E
AcO(H2C)4
K.; Asaka, S.; Uemura, M.; Mori, M. Chem. L&t., 1995,
80% 1055
REVIEW: “Palladium And/Or Copper-Mediated Cross-Coupling Reactions Between 1-Alkynes And Vinyl, Aryl, 1-Alkynyl, 1,2Propadienyl, Propargyl And Allylic Halides Or Related Compounds. A Review,” Rossi. R,; Carpita, A.; Bellina, F. Org. Prep. Proceed. Znt., 1995, 27, 129
SECTION
2: ALKYNES
FROM
A4CID DERIVATIVES
NO ADDITIONAL
SECTION
3: ALKYNES
FROM
ALCOHOLS
NO ADDITIONAL
SECTION
4: ALKYNES
FROM
EXAMPLES
AND THIOLS
EXAMPLES
ALDEHYDES
NO ADDITIONAL
EXAMPLES
Compendium
SECTION
5:
of Organic Synthetic Methods, Vol9
ALKYNES FROM AND ARYLS
ALKYLS,
NO ADDITIONAL
SECTION
6:
ALKYNES
FROM
7:
ALKYNES
AMIDES
FROM
EXAMPLES
AMINES
NO ADDITIONAL
SECTION
8:
ALKYNES
FROM
EXAMPLES
ESTERS
NO ADDITIONAL
SECTION
9:
ALKYNES FROM THIOETHERS
EXAMPLES
ETHERS,
NO ADDITIONAL
SECTION
10:
ALKYNES
METHYLENES
EXAMPLES
NO ADDITIONAL
SECTION
FROM
EPOXIDES
HALIDES
AND SULFONATES
HO.++K2C03
N.D.P, Synlett, 1995,
AND
EXAMPLES
-NO2
Pd/C , PPh3, CuI , DME
Bleicher, L.; Cosfwd.
Section 10
98% 111 5
Bu &@s. R.W.; Gabel, C.J.; Ji, J. Tetrahedron
Lett., 1994, 35, 6993
Section 15
SECTION
Alkynes from Misc.
11:
ALKYNES
FROM
HYDRIDES
For examples of the reaction RC=CH + R&C-C=CR1, (Alkyne-Alkyne). NO ADDITIONAL
SECTION
12:
ALKYNES
FROM
0
2
Ph I\
Taniguchi,
KETONES
Y.; Takai, K.; Fujiwara,
TMSC(Li)Nz,
THF
-78OC + reflux Me Miwa, K.; Aoyama. T.: Shioiri, T, Synlett, 1994,
13:
ALKYNES
FROM
14:
Ph
=
Ph
ALKYNES
FROM
67% Y. Chem. Lett., 199% 1165
*
P-Me
58%
107
NITRILES
NO ADDITIONAL
SECTION
*
-1OOC ,20 min
SiMe3
Y.; Fujii, N.; Makioka,
SECTION
EXAMPLF;
Yb,THF,HMPA
0
see section 300
EXAMPLES
ALKENES OSiPhzt-Bu
NaHMDS , THF -100°C Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron
SECTION
15:
ALKYNES
FROM
V
98%
L&t., 1994, 35, 3529
MISCELLANEOUS
COMPOUNDS
FVP (750°C) w t-Bu
Aitken. From A&ken. 1994,
=t-Bu
82% R,A,; Atherton, J.I. J. Chem. Sot., Per-kin Trans. l., 1994, 128 1 arylC0 derivatives: R.A.; Horsburgh, C.E.R.; McCreadie, J.G.; Seth, S. J. Chem. Sot., Perkin Trans. l., 1727
4
SECTION
Compendium
15A:
of Organic Synthetic Methods, Vo19
PROTECTION
OF ALKYNES
NO ADDITIONAL
EXAMPLB
Section 15A
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
Section 17
Acids from Acids
CHAPTER
2
PREPARATION
SECTION
16:
SECTION
OF
ACID
ACID DERIVATIVES
ACID
17:
DERIVATIVES
FROM
NO ADDITIONAL
EXAMPLES
DERIVATIVES
FROM
ALKYNES
ACID
DERIVATIVES
C02H HO
HaG,, @b, A BuLi, THF-HMPA
A I
v
*
OTs
+
6
Jv
d
OMe Me0
Me0
.
Kusumoto.T.;
1) 82% (10 Ichikawa, S.; Asaka, K.; Sato, K.; Hiyama, T. Tekhedron Lett., 1995,
36,
0 C02H
KF , microwave,
4 min 0
OAc
C02H <
-
ti 94%
Villemin.
D,; Labiad, B.; Loupy, A. Synth. Commun.,1993,
23, 419
O
1071
6
Compendium of Organic Synthetic Methods, Vo19
SECTION
18:
ACID DERIVATIVES THIOLS 02, Pb(OAc)p3
w
FROM
Section 22
ALCOHOLS
AND
H@ , Pd-C , lh w
lCH20H
w
lCH20H
90%
NaOH , H20,15O*C &@a. M; Nakano, S.; Sugiyama, T.; Tchitoh, K.; Nakao, H.; Akita, M.; More-Oh Chem. Sot. Jpn., 1993, 66, 15 11 TMS
1. PhI(OAck rt, 8h
Y, BUZZ.
, AcOH w
HOgg
2. H20 B Kirihara, M.; Yokoyama, S.; Kakuda, H.; Momose. T, Tetrahedron
SECTION
19: ACID DERIVATIVES
FROM
ALDEHYDES
H202, HCO,H PhCHO Dodd. R&; Le Hyaric, M. Synthesis, 1993, 295
t
NaClO2, aq. MeCN
phmCHo
10°C +
Babu, B.R.; Balasubramanlan..
92% Lett., 1995, 36,6907
93%
PhC02H
a
ph-co2H
rt
93% K.K. Org. Prep. Proceed. Int., 1994, 26, 123
NaN3-MnO$SiC14,
CH$$
0
, O*C
PhCHO
*
89% N3
Elmorsv. SS. Tetrahedron
SECTION
20:
Lett., 1995, 36, 1341
ACID DERIVATIVES FROM ALKYLS, METHYLENES AND ARYLS NO ADDITIONAL
SECTION
21: ACID DERIVATIVES NO ADDITIONAL
SECTION
22: ACID DERIVATIVES NO ADDITIONAL
EXAMPLES
FROM
AMIDES
EXAMPLES
FROM
AMINES
EXAMPLES
Section 25
SECTION
Acids from Halides
23: ACID DERIVATIVES
FROM
ESTERS
Other reactions useful for the hydrolysis of esters may be found in Section 30A (Protection of Carboxylic Acids). 0 Et2m3
Ph--CO$Ie Rawal.V.H,; Zhong, H.M. Tetrahedron
w
Lett., 1994,
35,
68% 4947
1.2 eq.KOWAliquat , microwave PhC02Me
w PhC02H 2. HCl Loupy. A,; Pigeon,P.; Ramdani,M.; Jacquault,P. Synth. Commun., 1994, 24, 159 CO (3 atm),8% PPh3 96h, rt * 2% Pd2(dba)$HC13 , toluene
PhMOCHO
PhMCOzH 92%(E only)
mote.
4. Bull. Chem. Sot. Jpn., 1995,
SECTION
24:
68, 433
ACID DERIVATIVES FROM ETHERS, EPOXIDES AND THIOETHERS 1. 10%[Bi(mandelate)&O DMSO , 80°C,30 min, air
Ph
* Ph-COOH 2. H30+ Zevaco, T.; Dufiach,E.; Postel.M, Tetrahedron Lett., 1993, 34, 2601
60%
C02H AgBQ , AlC13, MeCN reflux ,0.35h 02N
. . H; Mohammadpoor-Baltork, irouzabadl. I. Synth. Cornmun.,
SECTION
25:
ACID DERIVATIVES SULFONATES
FROM
C02, H2, 150°C, Id
02N
1994,
24,
HALIDES
95% 1065
AND
* MeC02H Ni(cod)2+ C%(C0)8 muoka. A; Gotoh, N.; Kobayashi,N.; Hirano,M.; I(omiva. S, Chem. Lett., 1995, 567 Me1
Compendium of Organic Synthetic Methods, Vo19
Section 29
REVIEW:
“PreparationOf Thiol Acids,Thiol EstersAnd AmidesBy Reactions Of CarbonylSulfides With GrignardReagents,” &&itzky. A&; Moutou,J.-L.; Yang, 2. Org. Prep. Proceed. Int., 1995, 27, 361
SECTION
26: ACID DERIVATIVES
FROM
HYDRIDES
NO ADDITIONAL EXAMPLES
SECTION
27: ACID DERIVATIVES
&
KETONES
c
C02H
Nag03’3/2 H202, 60°C
Cl
Yw
FROM
3h
86% C02H
D.T.C,; Cao, Y.H.; Kabalka,G.W. Synth. Commun., 1995, 25, 3695
SECTION
28: ACID DERIVATIVES
FROM
NITRILES
NO ADDITIONAL EXAMPLES
SECTION
29: ACID
DERIVATIVES
FROM
ALKENES
Fe(CO)5,KOH , CO (1 atm) H20/iPrOH, 55OC,4d \
Ph
*
p4zH
(96
‘xC02,,
.
4)
45%
Brunet.J.-J,; Neibecker,D.; Srivastava,R.S. Tetrahedron L&t., 1993,. 34, 2759
0”
HC02H, CO(6.8 atm), DME * Pd(OAc)2- dppb, 150°C, 16h
wco2H
86%
El Ali. B,; Alper, H. J. Org. Chem., 1993, 58, 3595
Ph \
HCOOH,6.8 atmCO 10%Pd/C, dppb, DME 150°C, Id
C02H 5c ph/\/co2H
+ PhA
(76 El Ali. B,; Vasapollo,G.; Alner. H, J. Org. Chem., 1993, 58, 4739
. ’
24) 65%
Section 30A
Protection of Acids
cat. 0~04, Jones reagent
C6H13
*
\ Henry, J.R.; Webeb.
85%
C6H13-C02H
acetone, rt S .pvt J. Org. Chem., 1993, 58, 4745 Pd/C , dppb , PPh3 , CO
u
HCOOH ,DME
*
Eco2’
Vasapollo, G.; Somasunderam, A.; El Ali, B.; Blper. H, Tetrahedron 02 ,2% Co(acac)3 , THF
PhCH=CH2
w
PhC02H
70°C, Id Reetz M.T,; Tollner, K. Tetrahedron
SECTION
30:
SECTION
PhCHO 14) 99%
(86
FROM
1. 0.1% Na2[PdC14] , CO , Hz0 Nag03 , 40°C ,6.5h
Grushin, V.V.; Alter.
+
Lett., 1995, 36, 9461
ACID DERIVATIVES COMPOUNDS
PhI02
60% Len., 1994, 35, 6203
MISCELLANEOUS
*
PhCOOH
71%
2. H30+ H, J. Org. Chem., 1993, 58, 4794
30A:
PROTECTION DERIVATIVES h
A&
P
Ph
OF CARBOXYLIC
5 TBAF@xH20 5BnSH *
0 ueki. M,; Aoki, H.; Katoh, T. Tetrahedron
PhCOOH
ACID
+
82% Lett., 1993, 34,2783
acidic Al203 ,7 min QPh
microwave
, CH2C12, rt
0
Yanna. R&; Chatterjee,AK; Varma, M, TetrahedronLett., 1993, 34,4603
quant
Ph
C02H 92%
10
Compendium
P
of Organic Synthetic Methods, Vol9
Section 30A
COzH 12, cyclohexane , rt
cossV,;
Albouy, A.; Scheloske, M.; Gomez Pardo, D. Tetrahedron
ematowicz,
1% TFA in CH2C12 ,5 min , rt MS,; Chao, H.-G.; Matsueda, G.R. Tetrahedron
L&t., 1994,
3.5,
1539
Lett., 1994, 35, 1651
CuC12, 02, aq. DMF Ph-C02H
phod ph 1 -R.N.;
Singh, L. Tetrahedron
1. NBS, (Bz0)2, Tco2Bn m.
2. H20
M&;
45%
Lett., 1995, 36, 5401 CC14 , heat -
r3:“”
Montana, J.G. Synlett, 1994, 219
REVIEW: “Recent Developments in Chemical Deprotection of Ester Functional Groups,” Salomon, C.J.; Mata, E.G.; Mascaretti, O.A. Tetrahedron, 1993, 49, 3691
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).
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
Section 32
CHAPTER
Alcohols from Acids
11
3
PREPARATION
OF ALCOHOLS
SECTION 31: ALCOHOLS AND THIOLS FROM ALKYNES 1. BH3eNEtzPh 2. BuLi
w-h7
3. BnBr 4. H202, OHReddy, Ch.K.; pe,w.
SECTION 32:
OH 62%
M, Tetrahedron, 1993,49, 8897
ALCOHOLS AND THIOLS FROM ACID DERIVATIVES BuLi , CeC13,THF OH
16h, -78OC
Bu
83%
Ahn, Y.; Cohen. T, Tetrahedron Lett., 1994, 35, 203 NaBH4-12,THF
OH
reflux McKennon, M.J.; Meyers. A.I.: Drauz, K,; Schwarm,M. J. Org. Chem., 1993, 58, 3568 Zn(BH& , THF , reflux Ph-COOH t Ph-CHzOH Narasimhan. S.; Madhavan, S.; Prasad,KG. J. Org. Chem., 1995, 60, 53 14
90%
Barton, D.H.R.; Castagnino,E,; Jaszberenyi,J.Cs. Tetrahedron Lett., 1994, 35, 6057
12
m
Compendium of Organic Synthetic Methods, Vol9
SmIrH20,l min PhCO2H . Y,; Kudo, T. Chem. Lett., 1993, 1495
Section 33
89%
PhCH20H
H2 (100 atm) , DME , 160°C C14H29C~H
-
Cl4H29CH20H
5% Ru/~1203---Mo(Co),
95% He, D.-H.; Wakasa, N.; Fuchikami. T, Tetrahedron Lett., 1995, 36, 1059 0 1. NaBH4, H20 PhA
N-
*
2. 10% aq. HCl
Ph-OH
85%
u harma. R,; Voymov, G.H.; Ovaska. TV,; Marquez, V.E. Synlett, 1995, 839
SECTION 33:
ALCOHOLS AND THIOLS FROM ALCOHOLS AND THIOLS OH
SH Lawesson’s reagent , toluene 67%
reflux o. T, J. Chem. Sot., Perkin Trans. I., 1993, 1113
MeO-{=)+OH
“‘EyF
*
MeO-(=)-OH
g3%
Kabalka. GW,; Reddy, N.K.; Narayana, C. Tetrahedron Lett., 1993, 34, 7667 4 SmI2,8 KOH OH
w
(-)-OH
+ <-)-OH
MeOH 10% Kamochi. Y*; Kudo, T. Tetrahedron Lett., 1994, 35, 4169 H
K
Geotrichium candidum immobilized with a water-adsorbent polymer
73%
OH +
hexane
* A Ph Ph 89%ee,R (56 Nakamura.; Inoue, Y.; Ohno, A. Tetrahedron Lett., 1994, 35,4375
..
Ph w
Section 34A
Reductionof Aldehydesto Alcohols
13
SECTION 34: ALCOHOLS AND THIOLS FROM ALDEHYDES The following reaction types areincluded in this section: A. Reductionsof Aldehydesto Alcohols B. Alkylation of Aldehydes,forming Alcohols. Coupling of Aldehydes to form Diols is found in Section 323 (Alcohol-Alcohol).
74%
amazaki. S, Chem.Lett., 1995, 127
SECTION 34A:
REDUCTIONS OF ALDEHYDES TO ALCOHOLS Na2Te, NMP , PhH
Ph-CHO . Suzulu.;
C
w
phJoH
80°C, 0.8h
59%
Nakamura,T. J. Org. Chem., 1993, 58, 241
00
*AWEt
Na
1. PhCHO , THF, 3h -
PhCH20H
2. H30+
+
PhCHO 50%
50%
Yoon. N.M,; Ahn, J.H.; An, D.K.; Shon, Y.S. J. Org. Chem., 1993, 58, 1941 I. (iPrO)2TiClfinEt@BH4 , CH2C12 -2OOC
phwcHo
Ravikumar, KS.; Baskaran,S.; Chandrw.
02N-i=j-CHO
m.
*
2. aq. Kg03
PheOH 90%
S, J. Org. Chem., 1993, 58, 5981
BH2zIH’3H7
w 02N-i=)-/‘”
M.k; Maiti, PK.; Bhaumik, A. Bull. Chem. Sot. Jpn., 1993,66, 810 [LiAlHq/IQ/LiH] Ph*CHO
= LiInH4 *
PhaOH 92%
Yamada,M.; Tanaka,K.; Araki, S.; Butsugan. Y, Tetrahedron Lett., 1995, 36, 3169
87%
Section 34B
Compendium of Organic Synthetic Methods, Vo19
14
Bu$nH , SiO2, rt CHO
CH2C12, Id
81% Chaboche, C.; Franck, X.; Peyrat, J.-F. .I. Org. Chem., 1995, 60, 7138
. &g&&&;
REVIEW: “P-Hydroxy Diisopinocampheylborane As A Mild, Chemoselective Reducing Agent For Aldehydes,” Cha.; Kim, E.J.; Kwon, 0.0.; Kwon, S.Y.; Seo, W.W.; Chang, S.W. Org. Prep. Proceed. Int., 1995, 27, 541
SECTION 34B:
ALKYLATION ALCOHOLS ASYMMETRIC
OF ALDEHYDES, FORMING ALKYLATIONS
Et2Zn Bn-Cl
*
-IO
Et
B 88% (83%ee) -Tf
Knochel. P,; Brieden, W.; Rozema, M.; Eisenberg, C. Tetrahedron Lat., 1993, 34, 5881
PhCHO
1. 10% R(+)2-binaphthol , Ti(OiPr)J CHzCl;! * 2 . Bu3Sm
,NaHC03
OH pL
71% (93%ee, R)
IQ&. GE,; Geraci, L.S. Tetrahedron L&t., 1993, 34, 7827 R-BJNOL$Ti(OiPr)4, MS 4A, TFA PhCHO -20°C, 14h ,
Keck. G&;
95% (96% ee) Krishnamurthy, D.; Grier, M.C. J. Org. Chem., 1993, 58, 6543
Section 36
Alcohols from Amides
15
CCl$HO , R-BINOL-Tic12 MS 4A, 0°C , CH2C12
..
-c4:,.+ [>95%ee]
(ilifkSH
0
cc13
[>95%ee]
Mikami. K,; Yajima, T.; Terada,M.; Uchimaru, T. Tetrahedron Mt., 1993, 34, 7591 mSnBu3
, MS4A, CH2C12 t 20% (binol)TiClz , rt , 2d
PhCHO
96% (82% ee , S) Costa, A.L.; Piazza, M.G.; Tanliavini, E,; Trombini, C.; 1[Jmani-Ronchi. A, J. Am. Chem. Sot., 1993, 115, 7001 1.
Ti(OiPr)dl,l’-bi-2-naphthol , MS4A CH2C12,reflux
PhCHO
-78OC,10 min 2. m
OH Phk
SnBu3 , -20°C, 70h
88% (95% ee, R) J(eck. G&; Tarbet, K.H.; Geraci, L.S. J. Am. Chem. Sot., 1993, I15, 8467 1. Et$Zn ,25OC, 10% Lie\\\\\ PhCHO 2.2N HCl 80% ee Mehler, T.; Martens.;
Wallbaum, S. Synth. Commun., 1993, 23, 269 1
1. ZnEt2 , 10%
CP
PhCHO
N H
11”1CPh20H
OH
2.2N HCl , -2OOC 100%ee Wallbaum, S.; m. J, Tetrahedron Asymmetry, 1993, 4, 637 With a chiral oxazoline additive, 60% ee J.m Tetrahedron Asymmetry, 1993, 4, 649 Allen, J.V.; Frost, C.G.; W-s.
16
Compendiumof Organic Synthetic Methods, Vol9
Section34B
1. BuLi 2. PhCHO
h
CPhzOH
OH
N Me
3. znEt2
4.2N HCl
Behnen, W.; Mehler, T.; Martens. TI Tetrahedron Asymmetry, 1993,4, 1413
OH
Et2Zn , toluene , hexane
PhCHO
98% ee , S
-
A 95% (85% ee, R)
Et
de Vries, E.F.J.; mee. 1987
Fit
J,; Kruse, C.G.; van der Gen, A. Tetrahedron Asymmetry, 1993, 4, OH
ZnEt2,5% iPr2NH
PhCHO
y i
5%
*
PhL
Ph-
quant. (46% ee , R) ShengJian, L.; Yaozhonrr. J,; Aiqiao, M.; Guishu, Y. J. Chem. Sot., Perkin Trans. I., 1993, 885 Et2Zn . PhMe , rt PhCHO
90% (96% ee , R) ao.
Rx;
Kim, N. Tetrahedron Lett., 1994, 35, 4115 CHo I
Me2Zn , PhMe , O°C, NHTf
Ti(Ot-Bu)4,8% TTPWI
I
a
NHTf
with Ti(OiPr)d - 80% yield, 0% ee Nowotng, S.; Vettel, S.; Mel, P, Tetrahedron Lett., 1994, 35, 4539
17
Alcohols from Amides
Section 36
Bu$n PhCHO , (R)-Binol +
0.5 Ti(OiPr), , -2O”d /
..
(14
1) 48%
>99% ee Keck. G.E,; Krishnamurthy, D.; Chen, X. Tetrahedron Lett., 1994, 35, 8323 PhCHO
OH
ZnEtz , hexaneftoluene, 10% chiral ligand 20°C, 28h
72% (80% ee) Perez-Encabo,A. Tetrahedron Asymmetry, 1994, 5,
And&, KM.; Martinez, M.A.; Pedro-; 67
ZnEt;! ,5% chiral ligand PhCHO
16h 70% (68% ee , R)
Ishizaki, M.; Fujita, K.; Shimamoto,M.; -0.
0, Tetrahedron Asymmetry, 1994, 5, 411
H
Et$Zn
PhCHO
*
Me%4 * N 3
P h\‘\\\c
Ph-L
SH
94% (100% ee)
Kanrz, J,; Lee, J.W.; Kim, J.I. J. Chem. Sot. Chem. Commun., 1994, 2009
CHO
P ’
0
Ph
Watanabe,M.; Soai.
\
OH
Et$n ,18h
0
Ph J. Chem. Sot., Perkin Trans. I., 1994, 3125
quant. (93% ee)
18
Compendiumof Organic Synthetic Methods, Vol9
Et$Zn ,22OC
H
PhCHO 10% Stingl, K.; w.
~111 CH (Mes)OLi
00
Section34B
) *
PhL 70-90% (86% ee , S)
N Bn
J, Liebigs Ann. Chem., 1994,49 1 Et$n , chiral ferrocenecatalyst
PhCHO
85% (55% ee , R)
toluene mawa.
S,; Tsudzuki, IS. Tetrahedron Asymmetry, 1995, 6, 1039
PhCHO CH2C12, -78OC
Phw 93% (79% ee)
I(obavashl.. S,; Nishio, K. Tetrahedron L&t., 1995, 36, 6729 Bu3Sn-
, CH2C12,MS * c7H15L 58% (87% ee) 20% Zr-BINOL derivative Bedeschi,P.; Casolari, S.; Costa,A.L.; Tagliavini, E,; Umani-Ronchi, A. Tetrahedron Lett., 1995, 36, 7897 C7H&HO
1. chiral Ti complex , ether Ph/
CHO *
2TFA,THF
pi0
OTMS 97% (80% ee) Singer, R.A.; &reira.
E.M, J. Am. Chem. Sot., 1995, 117, 12360
NON-ASYMMETRIC Sn(CH$H=CH& Ph-
ALKYLATIONS
, D-arabinose, rt
CHO 5% Sc(OTf), , aq. MeCN
Hachiya, I.; Kobayashi, S. J. Org. Chem., 1993, 58, 6958
*
PhL
98%
Section 36
Alcohols from Amides
/m
Ph
19
PhCHO , Et$n , THF cat. Pd(PPh& , rt ,3h
H I
0
-
PJJ
88% Yasui, K.; Goto, Y.; Yajima, T.; Taniseki, Y.; Fugami, K.; Tanaka, A.; Tamaru. Y, Tetrahedron Lett., 1993, 34, 7619 diethyl ether, -5OOC PhCHO
98% t-Bu-
Et
(<1:>99 syn;anti) Wissing, E.; Havennith, R.W.A.; Boersma, J.; Smeets, W.J.J.; Spek, A.L.; van Koten, G,J. Org. Chem., 1993, 58, 4228 BuCHO + t-BuCHgHO
t
Ph
Bu OH
PhTi(OiP& , -4OOC 2 MAPH , PhLi , -78OC
Ph
t-BuHg +
OH 1) 60% 10.8) 60%
.. ..
(3 3 (1’
MAPH = ArOAr, Ar = 2,5diphenylphenyl Maruoka, K.; Saito, S.; Conception, A.B.; Yamamoto. H, J. Am. Chem. Sot., 1993, 115, 1183 , THF/aq. HCl
C7H fi---CHO
20°C, lh
*
C7Hl5L
>99% Yanagisawa, A.; Inoue, H.; Morodome, M.; Yamamoto. H, J. Am. Chem. Sot., 1993, 115, 10356 e
SnBu3
, CH2C12, 25OC
PhCHO
83%
5% Ir(CO)(PPh&C104, 30h Nuss. J.M,; Rennels, R.A. Chem. Lett., 1993, 197 1. e
I
, SnC12.2 Hz0 *
PhCHO NaI,DMF
,hL
2,30%NH4F,H20 89% Imai, T,; Nishida, S. Synthesis, 1993, 395
20
Compendiumof Organic Synthetic Methods, Vo19
Section34B
1. Bu$nSiMe3, THF, rt 3h,Bu@CN
PhBCHO
2. H30+
SnBu3
Bhatt, R.K.; Ye, J.; Falck. J.R. Tetrahedron Lett., 1994, 35, 4081
m
PhCHO
SnBu3
5% Yb(OTf)3 85% Aspinall, H.C.; Browning, A.F.; Beeves N,; Ravenscroft,P. Tetrahedron Lett., 1994, 35,4639 mBr
,DMF,rrt *
ph/\/CHo GeI2 , lh
Phi 85%
Hashimoto, Y.; Kagoshima, H.; -0.
K, Tetrahedron Lett., 1994, 35,4805
OTIPS TIPS0
Ih40#‘,,, OTIPS /
1 C@ &HO , Me2AlCl , hexane -78OC,17h
SMe chirality
transfer
ene reaction
Masaya, K.; Tanino, K.; Kuwajima. I, Tetrahedron Lett., 1994, 35, 7965
BuGn-noMe :.I::b’” *-780zpJOMe
OMe
90% (70:30 de) Colombo. L,; DiGiacomo, M.; Brusotti, G.; Delougu, G. Tetrahedron Lett., 1994, 35, 2063 H
1. Li (powder) , naphthalene PhS02Et 2. Li (powder) , naphthalene * 3. PhCHO Guijarro, D.; m.
b& Tetrahedron Lett., 1994, 35, 2965
E -(I
61% Ph
Section 36
Alcohols from Amides
21
*3
SiMQ
sink3
l.Ga,KI,LiCl PhCHO , TI-IF , reflux w 2. H30+ H 4 Br
+ H
,8‘
x
Ph
Ph ..
(91 Han, Y.; Huansz. Y.-Z, Tetrahedron Lett., 1994, 35,9433
C,H7-
SnBug
-
cd413cHo
9) 95%
+
H
HO
w7
BuSnC13, CHCl3 , O°C
..
(98 Mipki.
2) 86%
H,; Yamamura, K. Chem. Lett., 1994, 897 10.5 CuCl , THF ) It
1. mBr
t
PhCHO 1.5 SnClp2 Hz0 , Id 2.30% aq. NI-IP
PhL 98%
T.Y; Nishida, S. J. Chem. Sot. Chem. Commun., 1994, 273
m
Ph EtCHO , Zn , aq. NH&I, Ph-Cl
Et
OH 98% (73:27) Rairama, R.; Ahonen, M. J. Chem. Sot. Chem. Commun., 1994, 1217
WR.; l
THF *
. .
cat. Pd(PPh& , PhCHO wso2ph
Et+,
THF , reflux
Ph 86%
Clayden, J.; lulia.M,
J. Chem. Sot. Chem. Commun., 1994, 1905
22
Compendiumof Organic Synthetic Methods, Vol9
mso2ph
l*
Section 34B
pd(pph3)4
2.2 Et2Zn , CgHlgCHO THF , reflux Clayden. JJ Julia, M. J. Chem. Sot. Chem. Commun., 1994,226l Ph PhCHzSiMe3, hv , MeCN
OSiMe3
Mg(C104)2, 6.5h
Fukuzumi. S,; Okamoto, T.; Otera. J, J. Am. Chem. Sot., 1994, 116, 5503 Cl 2: PhCHO ,THF , -78OC ’ Ba* c7Hyph+ C7H15
HO47Hfi
d
Ph ..
3) 80% (>99:1 E.-z) Yanagisawa, A.; Habaue, S.; Yasue, K.; mamoto. K J. Am. Chem. Sot., 1994, 116, 6130
(97
CHO
QH = MSnBu3
> InC13, acetone, Sh , -78OC+ rt (98:2 anti:syn)
Mar&B.
J.k; Hinkle, K.W. J. Org. Chem., 1995, 60, 1920 1. PhCHO , DMF , O°C
mSiQ3
2. H20 Kobavashi. S,; Nishio, K. J. Org. Chem., 1995, 60, 6620
Ph
Section 36
Alcohols from Amides
C@$rCpCi ,20% ZnBr2 * THF ,3h, 25OC
PhCHO Zheng, B.; Bebnik.
23
Hz0
88%
J. Org. Chem., 1995, 60, 3278 In, H20,30 min
PhCHO
Br&
-
::OH Ph
Br
75%
I& C-J, Tetrahedron Lett., 1995, 36, 517
Me 1. Ti(OiPr)4 , iPrMgC1
4
+
OH
HO
i Ph . 84) 81% (16 Harada,K.; Urabe, H.; Sate. FcTetrahedron Lett., 1995, 36, i203 Nakagawa,T.; Kasatkin, A.; Sate. F, Tetrahedron Lett., 1995, 36, 3207
~cHooo
1. TMSOTf, CH& MqS , -78°C
--
2. Bu$nCH2CH=CH2 -40°C 3. TBAF
d3 (>99
m.
:
OH
s; Kim, S.H. Tetrahedron Lett., 1995, 36, 3723
mBr
, aq. NH4Cl
QH
PhCHO sonoelectro-producedZn powder
-
Phb
82% Durant, A.; Delplancke, J.-L.; Winand, R.; Reisse,J. Tetrahedron L&t., 1995, 36, 4257 Brw
PhCHO
, Mg” , CuCI22 Hfi
,,Y-
99% THF,6h OH Sarangi, C.; Nayak, A.; Nanda, B.; Das. N.B.; Sharma,R.P. Tetrahedron Lett., 1995, 36, 7119
24
Compendium of Organic Synthetic Methods, Vol9
Section 34B
H Me$iw
Br siMe3
CHO In,HzO,rt Isaac, M.B.; &w,
--/“-
62% (7525 E:z)
T.-H Tetrahedron Lett., 1995, 36, 8957 0
CHO
+
0
+
BiClj-Zn , reflux
/
Ph
Ph . (74 Miyoshi, N.; Kukuma, T.; Wada, M. Chem. Lett., 1995, 999.
Ph 26) 85%
1. Ti(OiPr)z ,2 iPrMgBr /mBr
* -yPh 94% 2. PhCHO OH Kasatkin, A.; Nakagawa, T.; Okamoto, S.; Sate. F, J. Am. Chem. Sot., 1995, 117, 388 1 1. LDBB , THF , -78OC 2. MnC12 , THF , -78OC SPh LDBB = 4,4’-di-t-butylbiphenylide
CHo -78OC + O°C
OMe
84% (44:56) Ahn, Y .; Doubleday, W.W.; Cohen, T. Synth. Commun., 1995, 25, 3 3
PhCHO , 10% Pd(PhCN)g12 3 SnC122 H@ , DMI ,25OC MPMaz>’ 91% MPMO Kanq. S.-K,; Park, D.-C.; Park, C.-H.; Jang, S.-B. Synth. Commun., 1995, 25, 1359
Alcohols from Amides
Section 36
BrN
PhCHO
25
, Sn , Me$iCl 89%
Bu&Br , MeOH, rt ,4h Zhou, J.-Y.; Yao, X.-B.; Chen, Z.-G.; Wu. S.-H,Synth. Commun., 1995, 25, 3081
PhCHO
aSnBu3 ,THF,lt,4d * PhL
90%
pta2(pph3)2
Nakamura, H.; Asao, N.; mote.
w
Y, .I. Chem. Sot. Chem. Commun., 1995, 1273
13CHO
CH2C12-H20 (9.1 .. . H20, Bu$JBr (1 asuama. Y,; Kishida, M.; Kurusu, Y. J. Chem. Sot. Chem. Cohun.,
9) 48% 99) 48%
1995, 1405
REVIEW: “Synthetic Organoindium Chemistry: What Makes Indium So Appealing,” Cintas. P, Synlett, 1995, 1087
ALCOHOLS AND THIOLS FROM ALKYLS, METHYLENES AND ARYLS
SECTION 35:
No examplesof the reaction RR1 + ROH (R1 = alkyl, aryl, etc.) occur in the literature. For reactionsof the type RH + ROH (R = alkyl or aryl) seeSection 41 (Alcohols and Phenolsfrom Hydrides). NO ADDITIONAL EXAMPLES
SECTION 36: ALCOHOLS AND THIOLS FROM AMIDES 0 C6h3
LiBH3P-Pyr , THF, 25OC LA
*
N Pyr = pyrrolidino \3
Fisher, G.B.; Fuller, J.C.; Harrison, J.; Goralski, C.T.; Sinearam. B, Tetrahedron Lett., 1993, 34, 1091
(-13\/\OH
71%
26
Compendiumof Organic Synthetic Methods, Vol9
Section 39
SECTION 37: ALCOHOLS AND THIOLS FROM AMINES NO ADDITIONAL EXAMPLES
SECTION 38: ALCOHOLS AND THIOLS FROM ESTERS Pi,
180°C, 15h
e H+Bu 68% OBu Vega, F.R.; Clement, J.-C.; des Abbayes,H. Tetrahedron Lett., 1993, 34, 8117 Mg , MeOH, rt ,2.5h Me0 Y.-C,; Lebeau,E.; Walker, C. Tetrahedron Lett., 1994, 35, 6207
98%
1. PMHS , Ti(OiPr)J , THF Ph-C&Me
t
2. NaOH
PhCH20H
86$
PMHS = polymethylhydrosiloxane Breedon, S.W.; bwrence. N.J, Synlett, 1994, 833 1.2.5 eq. PHMS ,25% Ti(OiPr)d 65OC, Id CgHlg-COzEt t 2. aq. NaOH , THF Reding, M.T.; Buchwald. S.L,J. Org. Chem., 1995, 60, 7884 C7HfiCH2SAc
OH C9H19
93%
BER , Pd(OAc)z , MeOH, reflux w C7HfiCH2SI-I
BER = borohydride exchangeresin Choi, J.; Yoon. N.M,Synth. Commun., 1995, 25, 2655
SECTION 39:
/
98%
ALCOHOLS AND THIOLS FROM ETHERS, EPOXIDES AND THIOETHERS Bu,CuCNLi2,
THF OH
products are converted to alkenes via Swem oxidation and elimination
(95
Chauret, DC.; Bong, J.hl, Tetrahedron Lett., 1993, 34, 3695
+ :
Bu 5) 8040%
Section 39
Alcohols from Ethers
27
OH
OH
YJ
v
Al(Hg) , 10% aq. NaHC03
yield is 23% without ultrasound
also used Zn rather than Al(Hg)
ando Moreno. M.J.S SacMelo, M.L.; CamposNeves, A.S. hedron Lett., 1993:‘34, 353 Salvador, J.A.R.; S&eMelo. M.L,; CamposNeves, A.S. Tetrahedron Mt., 1993, 34, 361 l
Phi , Pd(PPh&$
, Zn , ZnCl2
Ph
THF,60°C,4h,NEt3 Duan, J.-P.; Chew. C-H, Tetrahedron Lett., 1993, 34,4019 1. LiI , MeCN , Amberlyst 15 rt, 30min MOTS
***+o = 3
= = &H
2. Bu$nH , AIBN , 80°C toluene ,2h
MOT,
Federici, C.; &i&i. G,; Rossi, L.; B Lett., 1994, 35, 797
99~88%
C,; Chiummiento, L.; Funicello, M. Tetrahedron
H2, Pd-C ,16h
t
P-OH HO
86%
Me
Bach, T, Tetrahedron Lett., 1994, 35, 1855
l\ aI
OH ’ 10% Pd(OAc)z
5 eq. NaO$H ,2 eq. BufiCl 3 eq. iPr2NEt , 80°C, Id N,N-dimethylacetamide Larock. RC,; Ding, S. J. Org. Chem., 1993, 58, 804
I (69:31 E.2)
70%
28
Compendiumof Organic Synthetic Methods, Vol9
zH *aa
Section 39
Mg , MeOH
,,,\I@ / BnO
7-L
C02Me
H
98%
p;als. CA; Lee, E.; Lee, G.H. J. Org. Chem., 1993, 58, 1523
Pd/C , HCO2NH4, EtOH
0 w-h7
OH /
Al
23OC, 2d
W-h
Dragovich. P.S,; Prins, T.J.; Zhou, R. J. Org. Chem., 1995, 60, 4922
A
81%
98% Beugelmans, R.; Bourdet, S.; Bigot, A.; Zhu. L Tetrahedron Lett., I994, 35, 4349
)
Te9LiBT3,n
)
I
TsO Kumar, A.; m.
4
D.C: Tetrahedron Let?., 1994, 35, 5583 L-Selectride , THF ,67OC, 12h
Wheless, K. Tetrahedron Let?., 1994, 35, 8727
1. TMSN3 , W(Nt-Bu)2(NHIt-Bu)2 ,5d w
Ph
2. H+
OH
95%
[ with Cr(Nt-Bu)2C12;12h - 95% ] Leunn. W.-H\; Chow, E.K.F.; Wu, M.-C.; Kum, P.W.Y.; Yeunrr. L.-L, Tetrahedron Let?., 1995, 36, 107
29
Alcohols Tom Halides
Section 40
Ph
5% SmI2(THF)z, CH2C12
NEt2
Et2NH,rt,18h
(100
OH
+
..
0)
63%
regioselectivity of addition reversedwith Me&N3 to form azide-OTMS Van de Weghe, P.; collin. Tetrahedron Lett., 1995, 36, 1649
0
TMSN3, Ph&bOH, PhH reflux ,2h
67% 19% .. Funwara. M.; Tanaka,M.; Baba, A.; Ando, H.; Souma,Y. Tetrahedron Lett., 1995, 36, 4849 l.e-,Ni(II),Mganode,DMF,rt mOPh
*
PhOH
2. Hz0 99%
Olivero, S.; Dufiach. E, J. Chem. Sot. Chem. Commun., 1995,2497 Additional examplesof ethercleavagesmay be found in Section45A (Protection of Alcohols and Thiols).
SECTION 40:
ALCOHOLS AND THIOLS FROM HALIDES AND SULFONATES
02N-(-)-Br :::v::02N-(-)
\a
Bieniarz. C,; Cornwall, M.J. Tetrahedron Lett., 1993, 34, 939
I
a.
.
/
Br
siMe3
1. Li dispersion, ether reflux 2. PhCHO , -1OOC lh
also works with ketones M; Hatano,K.; Kimura, M.; Watanabe,T.; Oriyama, T.; Koga, G. Tetrahedron Lett.,
1994, 35, 579
30
Compendiumof Organic Synthetic Methods, Vol9
Section42
1. Me3ZnLi , THF , -78OC
Ph-I
2. Me3Al, CHg12, O°C, lh
Ph 55%
Kondo, Y.; Takazawa,N.; Yamazaki, C.; Sakamoto.,J. org. chem., 1994, 59,4717
PhCHO -
PhCHCl2 2. NaB0~4 H@ ,2h
m
H
1. Bug , t-BuLi , -78OC
PC15
-
PhJL
G.W.; Lin, N.-S.; Yu, S. Tetrahedron Let?., 1995, 36;8545
Bu 64%
NHBn
NHBn
0 Yang, R.-Y.; Dai. I..-& Synth. Commun., 1994, 24, 2229
G Br
1. HC02NHEt3
CO2H 2.H20
80% J,; Renyer, M.L.; Veerapanane,H. Synth. Commun., 1995, 25, 3875
Mer.
SECTION 41: ALCOHOLS AND THIOLS FROM HYDRIDES
0\ /
1. e- , CF$02H, CH2C12,NEt3
*
2.H20
(t\ /
Fujimoto, K.; Maekawa, H.; Tokuda, Y.; Matsubara,Y.; Mizuno, T.; Nishiguchi.
OH 73% SYnlett,
1995,661
SECTION 42: ALCOHOLS AND THIOLS FROM KETONES The following reaction typesare included in this section: A. Reductionsof Ketonesto Alcohols B. Alkylations of Ketones,forming Alcohols Coupling of ketonesto give diols is found in Section 323 (Alcohol + Alcohol).
Section42A
Reductionof Ketones
31
SECTION 42A: REDUCTION OF KETONES TO ALCOHOLS ASYMMETRIC
REDUCTION OH = Z I
BH3, THF , 80°C w
> 90% (92% e-e,R)
P ii
Quallich. GJ,; Woodall, T.M. Tetrahedron Lett., 1993, 34,4145
Me
85% (76%ee,R)
2.1N HC1 P Me Balm. (3,; Elder, M. Tetrahedron Lett., 1993, 34, 6041 G. candidium
CQzEt N
C02Et cyclopentanol H20, 70h
(7193syn:anti)
Me QH E _=
immobilized G. candidium hexane ,3h cyclopentanol
-/I/
(955 syn:anti)
G. candidium = Geotrichum candidum
Nakmura. KJ Takano, S.; Ohno, A. Tetrahedron Lett., 1993, 34, 6087 0.6 BHpSMe2 , THF rt,clh Me
M
10%
PA
R
H *
Y H
OH = =
+
Phl
P&Me
Me
P ’ ‘Ph
82% (27%ee,S)
Bums, B.;,Studley, J.R.; Wills. M, Tetrahedron Lett., 1993, 34, 7105
1.ld4j~; P
P
Me$iCl Me
2.2N HCl
H *
C02Et = = = = I
PhL
Me
92% (84% ee, R)
&-&IL C,; Seger,A.; Felder, M. Tetrahedron Lett., 1993, 34, 8079
32
Compendium of Organic Synthetic Methods, Vo19
Section 42A
2. SmI3, THF , ICHgH21 3. quench quant. (97% ee , R) Evans. D.pL; Nelson, S.G.; Gag&, M.R.; Muci, A.R. J. Am. Chem. Sue., 1993, 115, 9800 OH
1. P-TADDOL complex , Ph2SiH2 , PhH
50% (29.5:70.5 R.-S)
r~mw112 2. TsOH , MeOH
-APh
TADDOL = a,a,a’,&tetraaryl-4,5-dimethoxy-1,3-dioxolane Jakaki, J.-i.; Schweizer, W.B.; Seebach. D, Helv. Chim. Acta, 1993, 76, 2654 Bakers yeast (cell free extract) OAc
Ishihara, K.; Sakai, T.; Tsuboi, S.; IJtaka, 0
OAc
NaDPH ,8h
62% (>99% ee, S) Tetrahedron Let?., 1994, 35,4569
[ (COD)Rh(DiPFc) 1’ OTf H
Ph A
60 psi H2 ,25OC ,4h
L Ph
OH
DiPFc = 1, l’-bis-(diisopropylphosphino)ferrocene quant. Burk. MJ,; Harper, T.G.P.; Lee, J.R.; KaIberg, C. Tetrahedron Let?., 1994, 35, 4963
dcl
loIH3@g;;
dcy%@l.7%e,sJ
Hong, Y.; &D. Y.; Nie, X.; Zepp, C.M. Tetrahedron Let?., 1994, 35, 6631 Ph
1. Ph$iH2 ,5% Rh-diferrocenylTHF , o”c dichalcoginide
Ph *
67% (50% ee , R) 2.0.5M HCI/MeOH 0 OH Nishibayashi, Y.; Singh, J.D.; Segawa, IS.; Kukuzawa, S.i.; Uemura, S, J. Chem. Sot. Chem. Commun., 1994,1375
Section 42A
Reduction of Ketones
Bakers yeast sugar
OH
SH
C02Et
+
CO2Et
C02Et
.. (77 55% ee Tetrahedron Asymmetry, 1994, 5, 403
Nielsen, J.K.; Madsen.
Me
33
/L
23
immobilized Geotrichum candidurn
i)H = =
w hexane 2-hexanol
Ph
MeA
Ph
73% (>99% ee , S) Nakamura. K,; Inoue, Y.; Ohno, A. Tetrahedron Lett., 1995, 36, 265 OH
0
OH Ph
OH
(-)-B -chlorodiisopinocampheylborane -15OC + OOC, THF, pyridine
Ph
99% (96.4% ee) . Shteh. W.-C,; Cantrell Jr., W.R.; Carlson, J.A. Tetrahedron Lett., 1995, 36, 3797 Hz, (S-BINAP)zRuBrz COzMe
* MeOH, rt ,48h
OH == =
C02Me
80% (97% ee)
Genet.; Ratovelomanana-Vidal, V.; Ctio de Andrade, M.C.; Pfister, X.; Guerreiro, P.; Lenoir, J.Y. Tetrahedron Lett., 1995, 36, 4801
iL
H2 , iPrOH , chiral bis-phosphine
H
>99% (87% ee, R) * PhL chiral bis-amine Ph Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Novori. R,, J. Am. Chem. Sot., 1995, 117, 2675
4
Ph
[RuC12(mesitylene)]2, KOH , 15h TolO$HN+
/-f
Ph
N
NH2
Ph
Hashiguchi, S .; Fujii, A.; Takehara, J.; Ikariya, T.; &yori. 7562
OH PhA 95% (97% ee, S) & J. Am. Chem. Sot., 1995, I1 7,
34
Section 42A
Compendium of Organic Synthetic Methods, VoI 9
1. Ph2SiH2 , THF , 1% RhCl(NBD)zL chiral ferrocenyl phosphine ligand
0
OH 90% (87% ee , S)
PhA 2. H30+ * PhA . Havashl. T,; Hayashi, C.; Uozumi, Y. Tetrahedron Asymmetry, 1995,6, 2503 1.0.1 chiraI diol , hexane , -3OC , catecholborane 2. H30+ quant. (82% ee) Giffels, G.; Dreisbach, C.; Kragl, U.; Weigerding, M.; WaIdmann, H.; Wa~&ey. C1,Angew. Chem. Int. Ed. Engl., 1995, 34, 2005
NaBH4, EtOH Co (P-oxoaldiminato) complex
99% (73% ee , S) Nagata, T.; Yorozu, K.; Yamada, T.; Mukaiyama. T,Angew. Chem. Int. Ed. En& 1995, 34, 2145
NON-ASYMMETRIC
o= 0
REDUCTION
1. CdCl$Mg (powder) THF,15min
OH
92%
2, H20
Bordoloi. M, Tetrahedron Lett., 1993, 34, 1681
t-Bb
. olrm
(-)
o
LiAIH(zt2cMe3)3
~
t-Bu
with LiAlH(OCMe3)3 - 90: 10 trans:cis Cr.; Deberly, A.; Toneva, R. Synlett, 1993, 585
(-)
OH
5:95 trans:cis
Cu(I1) exchanged cationic resin ‘.,u-(-=’
NaBH4, EtOH, O°C
*
t-Bu-(-)-oH 98%
Sarkar. A,; Rao, B.R.; Ram, B. Synth. Commun., 1993, 23, 291
35
Reduction of Ketones
Section 42A
& :;:I;;
&
Fuller, J.C.; Staangeland, E.L.; Goralski, C.T.; Sinearam.
o=
Tetrahedron Lett., 1993, 34, 257
iPrOH , SiO2-Zr catalyst
0
Inada.;
92%
OH
reflux
87%
Shibagaki, M.; Nakanishi, Y.; Matsushita, H. Chem. Lett., 1993, 1795
0
OMe TiC14, MeflBH4 t
Ph
CH2C12 , -78°C
Ki other reducing agents also used Sarko, CR.; Guch, I.C.; Dime.
t-Bu
do
(99 M, J. Org. Chem., 1994, 59, 705
Liz;;;;H7)2
t ,:
1)
:
93%
&OH
99% Harrison, J.; Fuller, J.C.; Goralski, CT.; Singaram. B, Tetrahedron Lett., 1994, 35, 5201 OH
0 1. Cp2TiC12/NaBHq, 5 min 2.1 N NaOH % Barden, M.C.; Schwartz. J, J. Org. Chem., 1995, 60, 5963
B 0
(MeO)3SiH , LiOMe , ether
Ph
-20°C, 9h
*HOlph (8
+
XPh .
92) quant.
wth (Me0)$iI-I/HMPA/LiOMe/O°C/2h + (9O:lO) 98% Hojo, M.; Fujii, A.; Murakami, C.; Aihara, H.; Hosomi. Tetrahedron Lett., 1995, 36, 571
36
Compendium of Organic Synthetic Methods, Vol9
Section 42B
Hz (8 atm) , cat. RuClz(Binap)(dmf), -H
iPrOH , diamine , KOH ,28OC
d Ph Ph Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori. R,J. Am. Chem. Sot., 1995, 117, 10417
cat. [NiClz(PPh&
0
, cat. NaOH
OH 82%
- PhA iPrOH , Ar ,3Oh, heat PhA lyer. &; Varghese, J.P. J. Chem. Sot. Chem. Commun., 1995, 465
SECTION 42B: ALKYLATION
OF KETONES, FORMING ALCOHOLS
Aldol reactions are listed in Section 330 (Ketone-Alcohol)
o=
Me
/
0
Hebri, H.; Duiiach.;
e’ , SmC13, DMF , 20°C
Perichon, J. Tetrahedron Lett., 1993, 34, 1475 3 eq. Me$=CH2 , THF 0 -1OOC -+ rt
91% Hamett, J.J.; Alcaraz, L.; Mioskowski, C.; Martel, J.P.; LeGall, T.; Shin, D.-S.; Falck. J.K Tetrahedron Lett., 1994, 35, 2009
C6H13
-0.
JL
e’7 CH3
DMF , -OH Bu#BF4
+
.,,,330H OH
89% T,; Morishima, Y.; Moriyoshi, N.; Ishifune, M. J. Org. Chem., 1994, 59, 273
Section42B
Alkylation of Ketones
37
1.2.2 eq. SmI2 , THF 2 eq. t-BuOH
t
2. H30+
53% (1:l) &lolander. G.A,; McKie, J.A. J. Org. Chem., 1994, 59, 3186 0.05 CeC13,lh , THF 0
1.1
:=\ -MgBr
93% rtrov. V,; Bratavanov, S.; Simova, S.; Kostova, K. Tetrahedron Lett., 1994, 35, 6713
mBr C02Et
, In 91Oh CO2Et
aq. MeOH
Br9 wlust o=
76%
Ii. C.-k, Lu, Y.-Q. Tetrahedron Lett., 1995, 36, 2721
0
THF , 1Sh
1.8 Et$Zn , Ti(OiPr)4 , hexane
PhCHO Hang.;
80%
usescommercialZn dust Majee, A.; Das, A.R. Tetrahedron Lett., 1995, 36,&B
Ranu.;
OH
-23°C , 0.1 chiral catalyst Guo, C. Tetrahedron Lett., 1995, 36, 4947
Ph
Me3Ti*MeLi , ether W-h
97% 99% ee, S
w
-5OOC
Et
* W-h
selective for conjugated ketones in the presence of non-conjugated ketones M&& I&; Leung, C.W. J. Am. Chem. Sot., 1994, 116, 371
78%
Compendiumof Organic Synthetic Methods, Vol9
38
Section42B
1. 10%CpzTi(PMe3)2,Ph#I-I2 1111111111
*
OH
6 >60%
Kablaoui, N.M.; Buchwald. S.L,J. Am. Chem. Sot., 1995, 117, 6785
e’ , MeCN , ZnBr2 Bu4N BF4
.
(95 Row
5) 85%
Y,; Derien, S.; DuWach,E.; Gebehenne,C.; Perkho;, J. Tetrahedron, 1993, 49, 7723
wBr *
+
Zn , aq. NH&l, THF
(54 Ahonen, M.; SiiSholm.
m’ PhL
..
46) 73%
Chem. Lett., 1995, 341
Ph
9PbCr(~eda) THF , -6OOC
Ph 77%
WiDf. P,; Lim, S. J. Chem. Sot. Chem. Commun., 1993, 1655
. 11.G,; Marcantoni, E.; Petrini, M. Angew. Chem. Int. Ed. En&
70% 1993, 32, 1061
39
Alcohols from Alkenes
Section44
SECTION 43: ALCOHOLS AND THIOLS FROM NITRILES 1. Li (excess), PhCHO , -3OOC + MeCN 5% 4,4’-his-t-Bu biphenyl 2. H20, HCl Guijarro, D.; Yus. M, Tetrahedron, 1994, 50, 3441
H 39%
Me-L
Ph
SECTION 44: ALCOHOLS AND THIOLS FROM ALKENES 1. Ti(BH& , 30 min CH2C12,-2OOC -2.10% K2CO3
c(,
+
aOH
1.2) 82% (1 Kumar, K.S.R.; Baskaran,S.; Chandrasekaran,S. Tetrahedron Lek., 1993, 34, 171 Me
Zn(BH& , DMF SiO2, rt ,30 min 30) 80%
(70 &nu. B.C,; Charkraborty, R.; Saha,M. Tetrahedron Lett., 1993, 34,‘4659
a
l.Mg*,THF,rt 2. ethylene oxide THF , -78OC 3. co2, oc + rt
OI-
0
a
OH 86% with Mg* = 8 Li, naphthalene,4 MgC12, THF, 3 Li H30+ at -78OC Sell, M.S.; Xiong, H.; We. R.D. Tetrahedron Lett., 1993, 34, 6007 6011 40°C 4. H30+ , 0°C + -9
o 69%
1.2 eq. Ph02BH, THF Nb catalyst, 25OC, Id 2. H202, NaOH Burgess.K,; Jaspars,M. Tetrahedron Lett., 1993, 34, 6813 also with CpzTiC14, see Burgess.K,; van der Donk, W.A. Tetrahedron L&t., 1993, 34,6817
40
Section 44
Compendiumof Organic Synthetic Methods, Vo19
By <=j
a
::R2isH~A1BN tBr (=)
\
SH
Hache,B.; Gareau.Y, Tetrahedron Lett., 1994, 3.5, 1837 buffered AD-mix-p , O°C OH
t-BuOH-Hz0 , MeS02NH2
70%
(70%ee)
Vanhessche,K.P.M.; Wang, Z.-M.; ms.
K.B. Tetrahedron Lett., 1994, 35, 3473
1. catecholborane, 10% SmI3,18h 2. oxidation
79% (5O:l 1”:2”)
WlW
OH Evans. D.A,; Muci, A.R.; Stiirmer, R. J. Org. Chem., 1993, 58, 5307
1. w
, -25OC
QH
w
2. oxidation
+L 74% (76% ee, S)
new asymmetricborane Dhokte, U.P.; Brown. H.C. Tetrahedron Lett., 1994, 35,4715
OH
1. Et2BH 2. Et$n
Ph
3. PhCHO , Ti(OiPr)J 0 NHTf 8%
*
“‘I NHTf
‘-0 67% (80% ee)
Schwink, L.; Knochel. P, Tetrahedron L&t., 1994, 35, 9007 OH 1.4 EtMgCl , ether, 25OC, 12m 5% cp$rC12
OH
2.02 , o”c Houri, A.F.; Didiuk, M.T.; Xu, 2.; Horan, N.R.; ItIQveyda A& J. Am. Chem. Sot., 1993, 115,6614
Section 45
41
Alcohols from Misc.
SiO;!, Zn(BH& , DME , rt -
w-b-
C~Hlf~OH
95% Ranu. B.C,; Sarkar, A.; Saha, M.; Chakraborty,R. Tetrahedron, 1994, SO,6579 1. Co(tdcpp) ,02, Et3SiH iPrOH , CH2Q PhJ
OH
2. P(OMe)y
tdcpp = 5,10,15,20-tetrakis(2,6-dichlorophenyl)porphinato a. Y *; Sugamoto,K.; Matsui, T. Chem. L&t., 1993, 925 1. HSiC13, MeO’/MOP , 40°C , Id PdCl(q3-C&)2 w 2. H202, KF , KHC03 Uozumi, Y.; Kitayama, K.; mashi. 68,713
SECTION 45:
81%
OH w-h3
A
83~71%(93% ee) T,; Yanagi, K.; Fukuyo, E. BUZZ.Chem. Sot. Jpn., 1995,
ALCOHOLS AND THIOLS FROM MISCELLANEOUS COMPOUNDS
f-k
1. MOM-Cl , iPr2NEt , CH2C12 2. 3.5 eq. Dibal
hv,CO,THF 65%
Merlic, CA,; Roberts,W.M. Tetrahedron Lett., 1993, 34, 7379
42
Compendiumof Organic Synthetic Methods, Vo19
Section 45A
l.TBAF,THF,rt C ~H2+WIe#Me3
*
G2H25--4H
2. H202, KHC03 MeOH, 40°C
65%
Suginome, M.; Matusnaga, S.; &o. Y, Synlett, 1995, 941
SECTION 45A: PROTECTION
l
Mezt-BuSi0+H2r;OSiEt3
OF ALCOHOLS AND THIOLS
PdI;xIeM;;Iin* 9
H~~CHZ<‘=~ 90%
Cormier. J.F,; Issac, M.B.; Chen, L-F. Tetrahedron L&t., 1993, 34, 243
J9 Al””
Py 9 CH2C12 $I
u
c13c
occ13
Burk. R.M; Roof, M.B. Tetrahedron Lett., 1993, 34, 395
OH I yy
OSiMe3 I
10% FS03H, rt, 30 min xs wSiMe3
YY
H
95%
Linshutz. B.H.; Burgess-Henry,J.; Roth, G.P. Tetrahedron Lett., 1993, 34,995 Bufi+ -OS02-0-OS020- BudN+ Pd\/O”
0.67 h ,
5, Pm
Q 95%
Jung, J.C.; Choi, H.C.; Kim. Y.H, Tetrahedron Lett., 1993, 34, 3581
xoH CAUTION:
. ~s.A.;
t-BuPhzSiCl , N&N03 DMF,ld NH6\J03 & NH4C104
OSiPhzt-Bu 87%
[w/ AgNO@nOH/15 min - 83%] arepotentially explosive Wijaya, N. Tetrahedronktt., 1993, 34, 3821
Section45A
Protectionof Alcohols
43
dihydropyran , CH2C12,rt BeOH
* [~(MecN)3~triphos)l PKl2 Ma, S.; Venanzi. LM, Tetrahedron Lett., 1993, 34, 5269
B”\/omp 99.5%
Bn
CH2C12, 20°C OH
. we.
see Tetrahedron L&t., 1988, 29,295l
B,; Franck, X.; Cave, A. Tetrahedron Lett., 1993, 34, 5893
z
1. BF3e2AcOH , CHgl;! rt ,20 set
02Me
Ph2S’ P Flem;
H
2. H202, KF , NaHC03
CO2Me
MeOH,THF,rt,3d
P*
*
77%
Winter, S.B.D. Tetrahedron Lett., 1993, 34, 7287 (-)w = =
OH = t =
1. “Cp$r” *
97%
2. H30+
Phi - see Tetrahedron Lett., 1986, 27,2829 CP2zr = Cp$Q/BuLi T,; Hanzawa, Y. J. Org. Chem., 1993, 58, 774
Ito, H.; -hi.
MoOz(acac)z, CH2(0Me)2, reflux PhCH20H Kantam. m;
Bn
\
/ CH2ho
w
PhCH2OCH2OMe 85%
Santhi, P.L. Synlett, 1993, 429 OTBDPS
7 BC136Me2, ether, Id w
,OTBDPS
Ho\ (CH2ho
93% Congreve, MS.; Davison, E.C.; Fuhry, M.A.M.; Holmes. AB,; Payne, A.N.; Robinson, R.A.; Ward, S.E. Synlett, 1993, 663
Compendiumof Organic Synthetic Methods, Vol9
44
0
a
Al203 Illi~OwWe
Section 4SA
,9 min OH
CMe3
89% Ley. S.V,; Mynett, D.M. Synlett, 1993, 793
1. Bu$n(OMe)2, PhH , reflux
HQJrJy 2.Phcilfrsmk 80% Boons, G-J.; Castle, G.H.; Clase, J.A.; Grice, P.; ky. S.V,; Pinel, C. Synlett, 1993, 913 dihydropyran , hexane BUMOH
*
HY zeolite , reflux , 1.5h 85%
I(umar. P,; Dinesh, CU.; Reddy, R.R.; uy.
R, Synthesis, 1993, 1069
dihydropyran , CAN, MeCN * rt,30min
/qOH Maity, G.; by.
*OTHP 91%
S.(z Synth. Commun., 1993, 23, 1667
m
dihydropyran , CHCl
MoOz(acac)z, reflux ,4h OH tam. M.L,; Santhi, P.L. Synth. Commun., 1993, 23, 2225
A+==-
Va
(CH&OAc
‘“zLa,30vec
t
OTHP
HO-{=)--
(CH2)30Ac
with 2.5 min of microwave, obtain 92% bis deacetylation 93% R&; Varma, M.; Chatterjee,AK. J. Chem. Sot., Perkin Trans. I., 1993, 999
MOM-Cl , Na-X-zeolite BUsOH w.
CH2Cl2 , reflux
*
BusOMOM 90%
P,; Raju, S.V.N.; Reddy, R.S.; Pandey, B. Tetrahedron L&t., 1994, 35, 1289
Section 45A
Protection of Alcohols
= P =
45
= S =
1.5% EtSH , 10% BF3QEt2 CH2C12 , -2OOC+ O°C 2. aq. NaHCO3
. m;
cleavage of THP ethers in the presence of other acid labile functional groups Mitra, A. Tetrahedron Let?., 1994, 35, 3033
c
Bu-OH
0
, Al203 , ZnCl2 w
r-t, 15min 90%
Ranu. BC,; Saha, M. J. Org. Chem., 1994, 59, 8269
94%
&&&
85%
C,; Saleh, S.; Blair, I.A. Tetrahedron Let?., 1994, 35, 7565
NHTMS
HOOC(CH2)yjOH
+
HOOC(CH&OSiMe3
cat. TBAF , CHg12, O°C
quant other silazanes can be used as well TanabfL Y,; Murakami, M.; Kitaichi, K.; Yoshida, Y. Tetrahedron Let?., 1994, 35, 8409 Ph
i=)
,OH
HIP-OH, DEAD, PP;
-4 LiNaphth , THF , -78OC HIP-OH = (CF3)2CPhOH Cho, H.-S.; Yu, J.; j&l&, J& J. Am. Chem. Sot., 1994, 116, 8354
86%
Compendiumof Organic Synthetic Methods, Vo19
46
5X
0
0
0= = = =
Dowex 5OW-X8,25h 90% MeOH C02Me *
x
Section 45A
Q = I5
P
C02Me
OBz OH
0J-J
OBz
87% Park, K.H.; Yoon, Y.J.; be. S.G. Tetrahedron Lett., 1994, 35, 9737
OH
OSiMe3
w 90%
Al203 ,3% H20,5 min Feixas, J.; Capdevila, A.; Guerrero. A, Tetrahedron, 1994, 50, 8539 OTHP NaCNBH3 , BF3aOEt2 rt ,2h
Srikrishna. A,; Sattigeri, J.A.; Viswajanani, R.; Yelamaggad,C.V. J. Org. Chem., 1995, 60, 2260 0-
1. AcCl , ZnCl;! , ether
OAc
OCH20Me 97%
2. MeOH, ether, iPr2NEt * u Bailey. W.F; &cone, L.M.J.; Rivera, A.D. J. Org. Chem., 199% 60, 2532 ii
*&CH&-
OCMezEt
10%TfOSiMezt-Bu , CH2C12 * rt
Br
Franck, X.; Finadere. B,; Cave, A. Tetrahedron L&t., 1995, 36, 711
OH
47
Protectionof Alcohols
Section45A
.,uOooMe
1%129MeOH
BnowOH
)
78% Vaino, A.R.; Szarek. W.A, Synlett, 1995, 1157
98% Yanada. R,; Negoro, N.; Bessho,K.; Yanada, IS. Synlett, 1995, 1261 PhCH20H
2 eq. dihydropyran , DMF , 60°C, 7h *
PhCH20THP
88%
0
I)+ I 0
Miura, T.; Masaki. Y, Synth. Commun., 1995, 25, 1981 dihydropyran ,5OC, 10 min * Envirocat EPZG
MOH
MOTHP
88% Bandgar. BP,; Jagtap,S.R.; Aghade, B.B.; Wadgaonkar,P.P. Synth. Commun., 1995, 25, 2211
(t
DDQ , MeCN , H20,5h OTHP
Raina, S.; Singh. V.K,Synth.
OH 90% Commun., 1995, 25, 2395
REVIEW:
“Silyl Ethers as Protective Groups for Alcohols. Oxidative Deprotectionand Stability Under Alcohol Oxidation Conditions,” Muzart. J, Synthesis, 1993, 11
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
48
Compendium
CHAPTER
OF ALDEHYDES
46: ALDEHYDES
FROM
ALKYNES
NO ADDITIONAL
SECTION
Ph
47: ALDEHYDES
a
Cha, J.S.; &own.
Section 48
4
PREPARATION
SECTION
of Organic Synthetic Methods, Vol9
FROM
AlH(O&Bu)3 Cl HL
EXAMPLFS
ACID DERIVATIVES
, diglyme-THF
81%
t Ph a
-78OC J. Org. Chem., 1993, 58, 4732
H
quant. Maeda, H.; Maki, T.; mri.
fL Tetrahedron
Lett., 1995, 36, 2247
1.2 eq. piperidine , THF , rt 2.2 eq. NaEtzAlH2,
rt , lh 74%
Yoon. N.M,; Choi, K.I.; Gyoung, Y.S.; Jun, W.S. Synth. Commun., 1993, 23, 1775
SECTION
48: ALDEHYDES
FROM
ALCOHOLS
AND THIOLS
Mn02, Bentonite microwave
CHO 60%
Martinez, 5293
L.A.; Garcfa, 0.; Delgado, F.; Alvarez. C,; Patifio, R. Tetrahedron
OMe L&t., 1993, 34,
Section 49
Aldehydes from Alkynes
49
TCM (trichloromelamine) CH2C12, rt ,2Oh PhCHzOH
83%
PhCHO
also oxidizes 2’ alcohols to ketones Kondo. S ,; Ohira, M.; Kawasoe, S .; Kunisada, H.; Yuki, Y. J. Org. Chem., 1993, 58, 5003 5% CpRu(PPh&Cl PhMOH
, 10% (C2H$#HPF6 *
8h
Ph”OH 90%
mt.
R.m;
Kulawiec,
R.J. J. Am. Chem. Sot., 1993, 115, 2027 hydrous zirconium (IV) oxide Me$iCl , PhCHO , xylene t
W-h~OH Kuno. H.; Shibagaki, 1699
dI \
C5H1 IBCHo
67% M.; Yakahashi, K.; Matsushita, H. Bull. Chem. Sot. Jpn., 1993, 66,
#OH
also for the preparation of ketones and 1,2-diketones Santagostino, M. Tetrahedron Lett., 1994, 35, 8019 Montmorillonite
K-10, pentane
)c KzFe04,3h Delaude, L.; Laszlo, P,; Lehance, P. Tetrahedron Lett., 1995, 36, 8505 PhloH
PhCH20H Mohand, S.A.; Muzart.
SECTION
88%
\
0
0
. WM.; .
d I
DMSO , rt
CHO
PDC/Adogen 464
t
PhCHO 63%
PhCHO
98%
J, Synth. Commun., 1995, 2.5, 2373
49: ALDEHYDES
FROM
ALKYNES
Conjugate reductions and Michael Alkylations of conjugated aldehydes are listed in Section 74 (Alkyls from Alkenes).
50
Compendium of Organic Synthetic Methods, Vol9
Phillips,
O.A.; Eby, P.; Maiti.
S.N,Synth. 1. Me@,
Section 51
Commun., 1995, 25, 87 KOH , Hfl
w
PhCHO 2. SiO2 Lemini, C.; Ordoflez, M.; Perez-Flores, J.; Cruz-Almanza.
PhCH2CH0
Synth. Commun., 1995,
25,
2695
1. a
2. H20
Ph”CHO
pf-d-dCHo
3. N&O3 Schummer. D,; Hofle, G. Tetrahedron, 1995, 51, 11219 Related Methods:
SECTION
50:
85%
Aldehydes from Ketones (Section 57) Ketones from Ketones (Section 177) Also via: AIkenyl aldehydes (Section 341)
ALDEHYDES AND ARYLS
FROM
ALKYLS,
METHYLENES
72x72% VeteIino, M.G.; (be. J.W. Tetrahedron
Hc-c=j-C,,
Let?., 1994, 35, 219
*r03
’ cAN’
g50c *
H+-CHO
70%
Ganin, E.; Amer. I, Synth. Commun., 1995,
SECTION
51: ALDEHYDES
FROM
25,
3149
AMIDES
NO ADDITIONAL
EXAMPLES
Section 53
Aldehydes from Esters
SECTION
52: ALDEHYDES
FROM
51
AMINES
1. BuLi
Bu
2. H30+ 98 x 70% ; Carter, D.S.; Dubree, H.J.P. Tetrahedron Lett., Related Methods:
SECTION
53: ALDEHYDES
c6
13
1993,
34,
3255
Ketones from Amines (Section 172)
FROM
ESTERS C
Bu$nH, PhH
13
SPh PhS h
H 0.4% Pd(PPh3)4
0
PhS *
C02Me
199 (E.-Z)
%f
Kuniyasu, H.; Ogawa, A.; Sonoda N, Tetrahedron Lett.,
93%
0
1993,
34,
2491
1.5% Cp2TiClfiuLi
OH
polymethyl-hydrosiloxane THF 2. workup Barr, K.J.; Berk, S.C.; Buchwald. S.L,J. Org. Chem., 1994, 59, 4323 NaAlH(NEt2)3 , THF ,6h w
mC02Et
65%
-CHO
65% Cha. J.S ‘; Kim, J.M.; Jeoung, M.K.; Kwon, 0.0.; Kim, E.J. Org. Prep. Proceed. Int., 27,95
1995,
Ca(BH& , 1,5-cod, THF *
CllH23C02Me
95%
CllH23CH20H
Narasimhan, S.; Prasad, K.G.; Madhavan, S. Synth. Commun.,
1995,
25, 1689
1. PhMezSiLi , THF, -1lOOC 2,
MeC02Me 2. CrO3,
DMSO , rt
Fleming. I,; Ghosh, U. J. Chem. Sot., Perkin Trans. I., 1994, 257
MeCHO
70x74%
52
Compendium
of Organic Synthetic Methods, Vol9
Section 55
REVIEW:
“Asymmetric Reductions of C-N Double Bonds. A Review,” Zhu, Q.-C.; Hutchins. R.Q, Org. Prep. Proceed. Int., 1994, 26, 193
SECTION
54:
ALDEHYDES THIOETHERS
FROM
ETHERS,
EPOXIDES
AND
LiCLO4 , ether
0 w Palani, N.; Balasubramanian.
*
rt ,6h K.K, Tetrahedron
cpCHO 60%
Lett., 1995, 36,9527
Bu
.. MABR , CH2C12, -2OOC (0 . SbF3 , PhH ,25OC (85 K.; Murase, N.; Bureau, R.; Ooi, T.; Yamamoto, H, Tetrahedron,
Maruoka,
LiTMP
,THF , 20°C
)
ClOH2lJ
Yanagisawa,
CloH21~cH0
83% A.; Yasue, K.; Yamamoto. H, J. Chem. Sot. Chem. Commun., 1994, 2103
Related Methods:
SECTION
55:
Ketones from Ethers and Epoxides (Section 174)
ALDEHYDES
FROM
HALIDES
AND SULFONATES
1. iPr$i-SH/KH 2. TBAF, THF PB’
100) 73% 15) 62% 1994, 50, 3663
H
* P
3. Hz0
88~73% Miranda, E.I.; Diaz, M.J.; Rosado, I.; Sode qu’st. J.A, Tetrahedron L&t., 1994, 35, 3221 Rane, A.M.; Miranda, E.I.; Soderauist, J,A: Titrahedron Lett., 1994, 35, 3225 30 atm CO , SiH(SiMe$y CSH
WI.;
, PhH
e W174HO AIBN , reflux 80% Hasegawa, M.; Kurihara, A.; Ogawa, A.; Tsunoi, S.; Sonoda 1743r
+ octane (16%) N,Synlett,
1993, 143
Section 58
Aldehydes from Nitriles
53
(f-o/ 02
0-d Br
vI
1. PhLi , THF , -78OC 2.
C
I v
l+CHO
Me Hardcastle, I.R.; C)Yilvle. P,; Ward, E.L.M. Tetrahedron
OMs
MeMgBr
Lett., 1994,
84% Me
35, 1747
OH
, THF
Cossv. J,; Ranaivosata, J.-L.; Bellosta, V.; Wietzke,
R. Synth. Commun., 1995, 25, 3109
CHBrz
CHO NaOAc , CaCO3,7h TBAB , H20, reflux
\
64%
I b
/
CHBr2 CHO S,; Liu, G.-B.; Sawada, T.; Tori-i, A.; Tashiro, M. J. Chem. Res. (S), 1995,
m.
SECTION
56: ALDEHYDES
FROM
SECTION
57: ALDEHYDES
FROM
1. TMSC(Li)Nz
.
reflux
. . . T, Synlett, 1994,
58: ALDEHYDES
FROM
CHO
, THF , iPr2NH
2. Hz0
K.; -T..
SECTION
EXAMPLES
KETONES
-78OC +
Pha
410
HYDRIDES
NO ADDITIONAL
Miwa,
CHO
-
02
t
*Phd 72%
109
NITRILES
NaAIH(NEt& , THF ,25OC PhCN PhCHO 97% Cha. J&; Jeoung, M.K.; Kim, J.M.; Kwon, 0.0.; Lee, J.C. Org. Prep. Proceed. Int., 1994, 583
26,
Compendium of Organic Synthetic Methods, Vol9
54
SECTION
59: ALDEHYDES
FROM
Section 59
ALKENES
Rh(acac)(CO)2, H&O 100 atm , 60°C, PhH ,42h
..
(90
10)
> 99% conversion Higashizima, T.; Sakai, N.; Nozaki, K.; Takava, H, Tetrahedron Lett., 1994, 35, 2023 Ph
4 eq. PhSH , EtflOTs , MeCN
* PhS-CHO e’ (0.05 F mol-‘) Yoshida. J,; Nakatani, S.; Isoe, S. J. Org. Chem., 1993, 58, 4855
77%
S.-Q, Jung, K.-Y.; Chung, J.-U.; Namkoong, E.-Y.; Kim, T.-H. J. Org. Chem., 1995, 60,4678
CHO H Hz, CO (1600 psi) t carbohydrate-OPAr2
n
8 8 OHC
\
/
\
/
\
+
53% conversion 51%ee(96 : RajanBabu, T.V.; Ayers. T.A, Tetrahedron Lett., 1994, 35,4295
Ph
CO,& [Rh(cod)IOAc)]2
4
+
Ph
CHO
(96 D~M.P.;
/ 1 / 1
Shanklin, M.S.; Zlokazov, M.V. Synlett, 1994, 615
..
4) 94%
Section 60A
55
Protection of Aldehydes
Rh(acac)(CO)rBINAPHOS
82% ee
Hz/CO (100 atm) , PhH , 60°C ,62h* A CHO Sakai, N.; Nozaki, K.; ma. I-l. J. Chem. Sot. Chem. Commun., 1994, 395 CO, Hz, 5% Rh(cod)L BF4 CHO
PhH, 55OC L = bis phosphine Ghan. A.S.C,; Pai, C.-C.; YanG T.-K; 2031
60:
phICHo
. (3 .5 1) Chen, S.-M. J. Chem. So;. Chem. Commun., 1995,
Related Methods:
SECTION
+
Ketones from Alkenes (Section 179)
ALDEHYDES COMPOUNDS
FROM
MISCELLANEOUS
MeCN , CuC12e2 Hz0 *
Ph Singh, L.; m.
H R&
H Synth. Commun., 1993, 23, 3139
H I NN
Ph L -N
TMSCl , NaN02, Ccl4 NH2
-)
Khan. Rx;
0 Mathur, R.K.; Ghosh, A.C. J. Chem. Res. (S), 1995, 506
SECTION
60A: PROTECTION
-Q AC
Vu.;
95%
PhCHO
Aliquat 336
K
P
P
OF ALDEHYDES
A1203 (neutral) , microwave w
-0Ac Chatterjee, AK.; Varma, M. Tetrahedron Ph Ph
PtiCHO
CH2C12, rt
2 eq. AgN02, rt, 30min
98% Lett., 1993, 34, 3207
12, THF 96% Ph
also for protected ketones also works with dithianes Nishide, K.; Yokota, K.; Nakamura, D.; Sumiya, T.; &de. M.; Ueda, M.; Fuji, K. Tetrahedron Lett., 1993, 34, 3425
56
Compendium of Organic Synthetic Methods, Vo19
Section 59
t-BuOK,THF,rt,2Omin t
P
I(u. Y.-Y.; Patel, R.; Sawick, D. Tetrahedron Ph
T
SPh
P+CHO
95%
Ox+ Lett., 1993, 34, 8037
DDQ , H20, MeOH )
hv (h > 350 nm)
SPh
Ph-CHO 95%
Mathew,
L.; sankararaman.
.I. Org. Chem., 1993, 58, 7576 p-TsOH , MgS04,
PheCHO
PhH
ethylene glycol , reflux ,4.5h *
phTJ 97%
Lu, T.-J,; Yang, J.-F.; Sheu, L.-J. J. Org. Chem., 1995, 60, 2931
HS
SH
, C&Q2
CHO CoBr$Si02,3
(t
min also with ketones
WY.
H.K. Tetrahedron
-CHO
99%
z&t., 1994, 35, 5717 SEt
2 EtSH , HY zeolite , CHg12 w 35OC
I MSEt
ketones can also be used
92% Kumar.;
Reddy, R.S.; Singh, A.P.; Pandley, B. Synthesis, 1993, 67 ethylene glycol , TsOH
ph-cHo
microwave,
2 min
ketones can also be used Monhaddam.
F.M; Sharifi, A. Synth. Commun., 1995,25,
2457
Section 60A
Protection of Aldehydes
57
MoOz(acac)z , MeCN ,4h
Kantam. b&;
PhCHO
Swapna, V.; Santhi, P.L. Synth. Commun., 1995, 25, 2529 1,2+%hanediol, cat. CAN
PhCHO
*
Ph
CHC13 , rt , overnight Mandal, PK.; Boy. S.C, Tetrahedron,
ketones can also be used 1995, 51, 7823
97%
85%
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
58
Compendium of Organic Synthetic Methods, Vo19
CHAPTER
Section 61
5
PREPARATION AND ARYLS
OF ALKYLS, METHYLENES
This chapter lists the conversion of functional groups into methyl, ethyl, propyl, etc. as well as methylene (CH2), phenyl, etc.
SECTION
61:
ALKYLS, ALKYNES H
P \ I c / . . . ~M.A.;
METHYLENES
AND ARYLS
1. C&-J&=CH , cat.CuCl cat. Pd(PPh)& , t-BuNH2 CC@Me PhMe,rt 2. PCC, CH2C12, rt 3. CHC13, CSA
I Weiss,T.J. Tetrahedron
Lett., 1994,
35,
1127
2.7 eq.TfOH ,22OC, 28h * Ph/ 2 eq. Cp(C0)3WH Luan, L.; Song,J.-S.; Bullock. =J. Org. Chem., 1995, 60, 7170
Masquelin,T.; Obrecht,D, Tetrahedron Lett.,
\ 0 I
&tori.
/
FROM
1994,
PhC=CH, 1,2-dichlorobenzene llO°C, 14h zeoliteHSZ-360
98%
35, 9387
Ph 40% yield (49%conversion)
G,; Bigi, F.; Pastorio,A.; Porto, C.; Arienti, A.; Maggi, R.; Moretti, N.; Gmppi G. Lett., 1995, 36, 9177
Tetrahedron
Section 61
Alkyls from Allkynes
(3 Rahimizadeh, M. Tetrahedron
Taber,;
59
.
1)
71%
Lett., 1994, 35, 6139
1. Rh(OAc)2 , PhH 2. air
Mueller, P.H.; Kassir, J.M.; Semones, M.A.; Weingarten, M.D.; pad= 1993, 34, 4285
A, Tetrahedron
L&t.,
PhOfi I
76% Grissom, J,W,; Klingberg,
D. Tetrahedron
Lett., 1995, 36, 6607
Wll
1. TaCl5 , Zn , DME/PhH 2.Py,THF 3. HC&---(CH2)4--C=CH 4. aq. NaOH
i w-b
Takai.;
, 50°C ,2h
CgH1
*
CsHIl
1
Yamada, M.; -to.
82% K, Chem. Lett., 1995, 851
60
Compendium of Organic Synthetic Methods, Vol9
SECTION
62:
ALKYLS, METHYLENES ACID DERIVATIVES NO ADDITIONAL
SECTION
63:
Section 64
AND ARYLS
FROM
EXAMPLES
ALKYLS, METHYLENES AND ARYLS ALCOHOLS AND THIOLS
Me;-“.
FROM
9“0I-L Me;oMe 70%
Bijoy, P.; &&&a Rao. w.R, C02Et
Tetrahedron
C#IflH , TMAD, PhH , DHTD-TBP
Lett., 1994, 35, 3341 Bu3P
CO2Et *
<
64% C3H
C02Et
4
C02Et TMAD = Me2NCON=NCONMe2 DHTD = 4,7-dimethyl-3,5,7-hexahydro-l,2,4,7-te~zocin-3,8-dione Tsudoda. T,; Nagah, M.; Nagino, C.; Kawamura, Y.; Ozaki, F.; Hioki, H.; 16, S. Tetrahedron Lett., 1995, 36, 253 1 C&l @CH20H
w
93%
w-wH3
2. Ph$iH , BEt3 r-t, 0.2h Tetrahedron, 1994, 50, 10193
Oba, M.; w
SECTION
1. PhNCS , NaH
64:
ALKYLS, METHYLENES ALDEHYDES BER-Ni(OAc)z
PhCHO BER = borohydride exchange resin Bandgar. BE; Kshirsagar, S.N.; Wadgaonkar,
AND ARYLS
FROM
, MeOH *
91%
PhCH3
P.P. Synth. Commun., 1995,
25, 941
Related Methods: Alkyls, Methylenes and Aryls from Ketones (Section 72)
Alkyls from Alkyls
Section 65
SECTION
65:
ALKYLS, ALKYLS,
METHYLENES METHYLENES
61
AND ARYLS AND ARYLS
FROM
1. e’ , 70°C , dioxanef5% H2SO4 2. Ph-C=C-CqLEt , 220°C ,4Sh _Ohno.T,; Ozaki, M.; Inagaki, A.; Hirashima, T.; NishQuchi. L Tetrahedron 2601
.
.
\w II\/\//\
Lett., 1993,34,
w N,; Kitmura,T.; Watanabe,K.; Yamaguchi,T.; Shigyo,H.; Ohta,T. Tetrahedron Lett., 1993, 34, 3421
OTf
t
v Pd(PPh&Clz
+
(2
/ I\ 1 I \ml / / \ 1)
90%
Rice. J.E,; Cai, Z-W. J. Org. Chem., 1993, 58, 1415
&
iIz*Lmp9m ~&
Flipin. L.A.: Muchowski, J.M,; Carter,D.S. J. Org. Chem., 1993, 58, 2463
89%
62
Compendium of Organic Synthetic Methods, Vol9
OH
OH
+
Section 65
OH
A
2 eq. AlCl3 ,2 eq. FeC13
I v
50°C, lh
5,
OH
6
A
I v
I v
OMe 48Y ; Maggi, R.; Bigi, F.; Grandi, M. J. Org. Chem., 1993, 58, 7271 0
.
(4
OMe
56) 77%
Hashimoto, Y .; Hirata, K.; Kagoshima, H.; Kihara,N.; Hasegawa, k; Saieo.K. Tetmhedmz, 1993,
49,
5969
0\/
H
H
5 q. H2SO4,reflux ,3.5 h
(=K-)
68%
yieldbasedonmolesof alkylatingagent
Chung,K.H.; Kim, J.N.; mu. E.K, Tetrahedron
Lett., 1994, 35, 2913
1. s-BuLi.TMEDA , -9OOC , THF 2. Me1, -78OC
Me 65%
3. H30+ Mortier. J,; Moyroud, J.; Bennetau,B,; Cain,P.A. J. Org. Chem., 1994, 59, 4042
CO2Me
Zn dust
Alkylation alsooccurswith benzylic andallylic halides Mood. N.& Nosal,R. Tetrahedron Lett., 1994,35, 3669
97%
Section 65
63
Alkyls from Alkyls
83%
BilluDs. W.E,; M&or&
m.
D.J.; Maughon, B.R. Tetrahedron Lett., 1994, 35, 4.493
T,; Fujii, T.; Ohshiro,Y. Tetrahedron mt2
Lett., 1994, 3.5, 8005
1. see-BuLVWEDA 2. CubSMe
Meoa I v
3. Br78%
Casas,R.; Cave,C.; d’Angelo,J. Tetrahedron
Lett., 1995,
36,
1039
Ph;BiF2, BFpOEt2, CHg12 Me3Siw -0.
t
-78OC
Y,; Yoshimune,M.; &zuki. )t Tetrahedron
aCU/CU(ClO4)2 Ban&. J.B, Tetrahedron
45%
Lett., 1995,
36, 7475
OH
OH
Lett., 1995, 36, 8509
Ph-
Section68
Compendium of OrganicSyntheticMethods,Vol9
64
SECTION
66:
ALKYLS, AMIDES
METHYLENES
AND ARYLS
FROM
NO ADDITIONAL EXAMPLES
SECTION
67:
ALKYLS, AMINES
METHYLENES
AND ARYLS
FROM
NO ADDITIONAL EXAMPLES
SECTION
68:
ALKYLS, ESTERS
METHYLENES
AND ARYLS
FROM
Ph ohm.
.
83% Y,; Ikeda, E. .I. Chem. Sot. Chem. Commun.,
1789
1994,
A
, ether, 0.C *
Bu
BuMgI (120min addition)
PhO
quant(34%ee) PhO vanKlaveren,M.; Persson, E.S.M.; de1Villar, A.; Grove,D.M.; Backval1,J.-E. Tetrahedron Lett., 1995, 36, 3059
/ o( N
0
10%Ni(acac)z,20% AlEt toluene, reflux , PPh3
\ +
PhB(OH)z
Ph -o! .
Trost.;
(2 1 Spagnol,M.D. J. Chem. Sot., Perkin Trans. i., 1995, 2083
6 1) 70%
Ph
Section 70
SECTION
Alkyls from Halides
69:
ALKYLS, ETHERS,
65
METHYLENES AND ARYLS FROM EPOXIDES AND THIOETHERS
The conversion ROR + RR’ (R’ = alkyl, aryl) is included in this section.
95% M.: Blum. J, J. HeterocycEic Chem., 1993, 30, 29 1
Elmalak, 0.; &&i,~ov&.
Li+ -BuB(allylh , TMSOTf , THF , -78OC
OMe
Ph ) Hunter. R,; Michael,J.P.; Tomlinson,G.D. Tetruhedron,
SECTION
70:
ALKYLS, HALIDES
1994,
Phk 94%
50, 871
METHYLENES AND ARYLS AND SULFONATES
FROM
Thereplacement of halogenby alkyl or aryl groupsis includedin thissection.For the conversionof RX + RH (X = halogen)seeSection160(Hydridesfrom Halidesand Sulfonates). OH
Br
1. hv 9c6D6
Cl
h
9@u3Snh
2. I2 , DBU
57%
(80:20 , tranxcis)
Huval, CC.; Sinnleton.D.A, Tetrahedron Lett.,
1993,
34,
3041 h
1. “activated”Zn , 83% 2. 5%Pd(PPh3)4,Phi rt, 18h S02Ph S02Ph Sakamoto.TJ Kondo,Y.; Takazawa,N.; Yamanaka, H. Tetrahedron Lett., 1993, 34, 5955
Section70
Compendium of OrganicSyntheticMethods,Vo19
66
1. Zn* , ether, 20°C 2. H-30+
Bu
Bu Meyer, C.; -I.;
Courtemanche, G.; Normant.J.-F, Tetrahedron
60% (73:27cis: trans) L&t., 1993,34, 6053
t Pd(PPh3)4 , CuI-DMF 48h Levin. J.I, Tetrahedron
Lat.,
1993,
34,
6211
Mg , THF heat OMe
(90:10 S:R)
OMe Moorlag, H.; Mevers. AI, Tetrahedron
L&t., 1993, 34, 6989, 6993
1.Zn , DMSO , THF , 0°C 2. CuCN, THF , LiCl
Knochel,;
Ph
Chou,T.-S.; Jubert,C.; Rajagopal,D. J. Org. Chem., 1993, 58, 588 3 eq.PhMgCl, ether, 35OC 1.5ZnC12edioxane Ph
I * A/ 10%NiClz(dppf) A/ Park, K.; Yuan, K.; Scott. W.J. J. Org. Chem., 1993, 58, 4866 BuMnCl ,3% CuClqLi2 W19-Br
THF/NMP,rt, lh
Cahiez. G,; Marquais,S. Synlett,
1993,
45
*
W-b-BU
72%
93%
Section 70
Alkyls from Halides
67
PhCHO , -78’ + rt
Li B
Ph
J,; Montserrat,
J.M.; Florez, J. .I. Org. Chem., 1993, 58, 5976
Br
1. BuLi , -4OOC , hexane:THF 2. ally1 bromide , rt
Wu, X.; Chen, T.-A.; Zhu, L.; Beke. Itlz
Tetrahedron
Lett., 1993, 34, 3673 ,OMe
1. e’ , ZnBr2, Ni(BF&bpy3
2.
Fe-(=)Cl
Sibille, S.; Ratovelomanana,
Pd(PPh3)2C12, DMF Fc V.; Nedelec, J.Y.; Perichon, J. Synlett, 1993, 425 Bugn-2
Ph
LiCl , HMPA
Phacl Arai, M.; Kawasuji,
T.; m.
93% v
Bu
E, Chem. Lett., 1993, 357
1. CH2=CHCH2SnBu3 2. HBr , hv
, AIBN
3. Bu$nH
-ca 51X97X51% Lett., 1994, 35, 3865
, AIBN
,G .; Dowd. P, Tetrahedron
1.5% KOH , NaBH4
Rai, R.; Collum. DLB, Tetrahedron
Lett., 1994, 35, 6221
0
C02H
Compendium of Organic Synthetic Methods, Vol9
Section 70
64%
Hatanaka. YJ G&a, K.; m
(58% 9R)
T, Tetrahedron Lett., 1994, 35, 1279
Zn , KI , 10%NiClz(PPh& 67OC, THF ,4h
Jutand. A,; Mosleh,A. Synlett, 1993, 568 F ClZn I xx
\
0
/
0
5%Ni(acac);!, THF PPh3, 10%Dibal >
F
\ -u-
/
OTf l-t
Quesnelle,C.A.; Familoni,0.B .; Snieckus.V. Synlett, Phi , NiBrz(bipy) , DMF Ph
e’ 9 Bu&IBF4 54%
Drandetti. M,; Sibille, S.; Nedelec,J.-Y.; P&ichon, J. Synth. Commun., 1994, 24, 145 OTf
C6&3
9
Me2(CN)CuLipTHF -78OC-+ 25OC
60% * Y 50, C6H
3
OTf Martinez. A.G,; Barcina,J.O.; Diez, B.R.; Subramanian, L.R. Tetrahedron, 1994,
13231
Section 70
69
Alkyls from Halides
Br
THF, 120°C, 12h 0
0 w/ 5% PdC12(dppp)/TBAF/THF/20°C - 7 92% 4-(-CHzCH=CHMe) - 7.2 E/Z Hatanaka,Y;, Goda, K.; Hiyama, T. Tetrahedron Lett., 1994, 35,651l
97%
Percec. V.; Bae, J.-Y.; Hill, D.H. J. Org. Chem., 1995, 60, 1060
Me-(=)-1
PhSnCl3,O.Ol
PdCl2
b
Me,-{=j-Ph
aq. KOH , lOO”C, 3h 86%
Roshchin, A.I.; Bumanin. N.A,; Beletskaya, I.P. Tetrahedron 1. MeZnBr ,5% PdC12(PPh3)2 DMF , 12h C02H
Lett., 1995, 36, 125 Me *
C02H
2. aq. NH4Cl 95%
Abarbri, M.; Parrain, J.-L.; Duchene. A, Tetrahedron
Lett., 1995, 36, 2469
NaBH4, CpzTiCI2 DMF ,75OC Liu, Y.; Schwartz. J, Tetrahedron,
Kodomari.
1995, 51, 4471
L o-l% ZnCldSiO2, K2CO3 Alf13, 30°C, lh M,; Nawa, S.; Miyoshi, T. J. Chem. Sot. Chem. Commun., 1995, 1895
57%
70
Compendium
of Organic Synthetic Methods, Vo19
Section 7 1
10% Pd(PPh& , 10% aq. TlOH DMA , 20°C DMA Anderson.
= dimethylacetamide
JC,; Namli, H. Synlett, 1995, 765 Et$n ,20% LiI , THF , -35OC 7.5% Ni(acac)z, 18h * Et+,
81%
Br fi Devasagayaraj, A.; Stiidemann, T.; JCnochel. P,Angew.
Chem. ht. Ed. Engt., 1995, 34, 2723
SECTION
AND ARYLS
71:
ALKYLS, METHYLENES HYDRIDES
FROM
This section lists examples of the reaction of RI-I + RR’ (R,R’ = aIky1 or aryl). For the reaction C=CH + C=C-R (R = aIky1 or aryl), see Section 209 (Alkenes from AIkenes). For alkylations of ketones and esters, see Section 177 (Ketones from Ketones) and Section 113 (Esters from Esters). (CH2)6--H
F&---cH&-H , TBi@, THF 5% Pd(PPh3)4, 1UWC
Matsuhashi, H.; Juroboshi, M.; Hatanaka, Y.; Hivama. T, Tetrahedron Lett., 1994, 35, 6507 C02H AI
\
1. s-BuLi/TMEDA-THF -98*C + -78OC 2. Me1 3. H+
Cl er. J,; Moyroud,
C02H I 62%
J.; Guesnet, J.-L. J. Chem. SW, Perkin Trans. I., 1995,
Section 72
Alkyls from Ketones
71
Si(OEt)3
, toluene ,2h 93% 4% Ru(H)2(CO)(PPh3)3 reflux Si(OEt)3 Kakiuchi, F.; Sekine, S.; Tanaka, Y .; Kamatani, A.; Sonoda, M.; Chatani, N.; Murti. S, BUZZ. Chem. Sot. Jpn., 1995, 68, 62
SECTION
72:
ALKYLS, KETONES
METHYLENES
AND ARYLS
FROM
The conversionsR2C=O+ R-R, R2CH2,R2CHR’,etc. arelistedin this section.
1) 66%
(3 5 Taber.D.F,; Wang,Y.; Stachel,S.J. Tetrahedron Lett.,
Id93,
34, 6204
Kim. CU.; Misco, P.F.; Luh, B.Y.; Mansuri,M.M. Tetrahedron
Me0
Lett., 1994, 35, 3017
\/
Yli-Kauhaluoma,J.T.; Janda.
MeOTetrahedron
g3v0
Lett., 1994, 35,4509
Et0
I 6 NaOEt,2 12 EtOH , -78OC
ende p Me 0 H . . ,; Kassim,A.M.; Ingrum,A.I. Tetrahedron Lett., 1995, 36, 8395
66% OH
72
Compendium of Organic Synthetic Methods, Vol9
c
, t-BuOK
Section 74A
t
ZO%MeOH,rt,ld
67%
0
Coe, J.W; Vetelino, M.G.; Kemp, D.S. Tetrahedron
1. MeMgBr 2. VC12(tmeda)2 * 3.
Lett., 1994, 35, 6627
Ph
Ph
+
wBr s
Ph 50% I.; Akiyama, H.; Tani. K, Tetrahedron Lett., 1995, 36,6495 i”’I
Kataoka, Y.; Makihira,
SECTION
73
ALKYLS, NITRILES
METHYLENES NO ADDITIONAL
SECTION
74:
ALKYLS, ALKENES
AND ARYLS
FROM
EXAMPLFS
METHYLENES
AND ARYLS
FROM
The following reaction types are included in this section: A. B. C. D. E. F.
Hydrogenation 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 halocyclopropanations
SECTION
74A: Hydrogenation
of Alkenes (and Aryls)
Reduction of aryls to dienes are listed in Section 377 (Alkene-Alkene). [ (t-Bu2Ph)PdPt-Bu]2 Jso2ph
TfEH2
Cho, 1.S.; AIPer. H, J. Org. Chem., 1994, 59, 4027
/ 02
w
46%
Section 74A
Hydrogenation of Alkenes
73
“colloidal palladium” Hz, ether, 25OC “colloidal palladium” = [TMS(OSiHMe),OTMS]Pd(hfacach Fowley, L.A.; Michos, D.; Luo, X.-L.; Cr;ibtree. R& Tetrahedron Mt.,
1993,
34,
3075
chirti catalyst, H2, 65OC Ph
Ph
Broene, R.D.; Buchwald. SL, .I. Am. Chem. Sot.,
91% (>99% ee) 115, 12569
1993,
Hz, rt , lh , MeOWH20 RuC13,
TOA
TOA = trioctylamine Fache, F.; Lehuede, S.; LeMaire. M, Tetrahedron Lett., Ph 0 Cho, I.S.; Lee, B.; m
1995,
36,
99% (ciskans = 1.5) 885
[ (t-Bu2PH)Pd(Pt-Bu)2]2, H2 ,02 THF/CH2C12,6h
Tetrahedron Lett., 1995, 36, 6009
aq. Ba(OH), , NiAl(Raney alloy) 54%
60°C, lh
Br Br Tsukinoki, T.; Kakinami, T.; Iida, Y.; Ueno, M.; Ueno, Y.; Mashimo, T.; Tsuzuki, H.; Tashiro, M. J. Chem.Sot. Chem. Commun., 1995, 209 H2, [ W2(~&t’BU)6(@)2
1
Barry, J.T.; Chisholm.M.H, .I. Chem. Sot. Chem. Comma,
1995,
no yield 1599
74
Section 74B
Compendium of Organic Synthetic Methods, Vo19
SECTION
74B: Formation
of Aryls
OMe / LiCl , CuBr , inhibitor Pd(PPh& , dioxane , reflux
OMe &.& J.M.; MartoreU,G. J. Org. Chetn.,1993, 58, 1963
Crrissom, J.W,; Calkins, T.L.; McMillen,
bMe
H.A. J. Org. Chem., 1993, 58, 65% 50 at.mCO, AC@ PdCl2W’bh 9 mt3
PhooAc
PhH , 140°C, 3h Ishii, Y.; Gao, C.; Xu, W.-X.; Iwasaki,M.; Hidai. MJ.
C
*
OAc 69% Org. Chem., 1993, 58, 6818
HSiMe$-Bu , C) (50 atm) Ru~(CO)~~/PCY~, 140°C,20h
*
*:::: 45%
Chatani, N.; Fukumoto, Y.; Ida, T.; Murai.
S, J, Am. Chem. SM., 1993, 11.5, 11614
PhOH , PhMe ,180”C t
7h %
0
Danheiser, R.L,; Gould, A.E.; de la Pradilla, R.F.; Helgason, A.L. J. Org. Chem., 19%
5514
5%
Section 74B
75
Formation of Aryls
20% Ni(O)-PPh3 , HC=CH N---Ts THF,23OC, 12h 91% Sato, Y.; Nishimata, T.; Mori. M, .I. Org. Chem.,
1994,
59, 6133
1. PhNH2 2. Pd(OAc), , MeCN PhCHO B
;-;FHT3/
.
0
AQtZ
RamaRao.AV,; Reddy,K.L.; Reddy,M.M. Tetrahedron Lett.,
1994,
35,
5039
OH 1.5 I
y
~wipr)3
t
I
0.1SnC14, 0°C 1.5 (MeO)$iMe3
s 78% -Si(iPr)3
Angle. SR,; Boyce,J.P. Tetrahedron
Lett., 1994,
35, 6461
t-BuOOCOPh, Cu(OAc), CuBr , PhH , 80°C, 8.5h
56% Tavares,F.; Mevers. A.1, Tetrahedron Lett., 1994, 35, 6803 N-OH Bn
5% Pd/C, diethyleneglycol 188OC , diethyl ether, 45 min
Bn 89%
I Ar Ar = 4-methoxyphenyl Matsumoto.M.; Tomizuka,J.; Suzuki, M. Synth. Commun.,
1994,
24,
Al1441
76
Compendium
SECTION
74C: Alkylations
Section 74C
of Organic Synthetic Methods, Vol9
and Arylations
of Alkenes
2 BFjmOEt2 25OC
Maietich. G,; Zhang, Y.; Feltman, T.L. Tetrahedron L&t., 1993, 34,441 . Maretich. G,; Zhang, Y.; Feltman, T.L.; Duncan Jr., S. Tetrahedron Lett., 1993, 34, 445 Ar
/OH Ph Toluene , -45OC , 18h 2. LiEt3BH 3. MeOH 4. NaBH4
. Tomloka.;
Ar = 2,6-di-t-Bu-4-OMephenyl Shindo, M.; Koga, K. Tetrahedron
N
M
/
80%
(84% ee)
Lett., 1993, 34, 681
+3-l”l
H
DMF , BuflCl , ld 10% Pd(OAc)z ,3 iPr2NEt 66:34 E.-Z, 99% 5 HC02Na Ding, S. Tetrahedron Lett., 1993, 34, 979
%
0
Larock.;
w-4
1
Me
cat. Pd(OAc);? , Ag2C@ DMF ,45OC, overnight
C02Me Wll
OH OH &ff@.
T, Tetrahedron
L&t., 1993,
34,
1133
NH2
75%
Section 74C
Alkylation of Alkenes
77
Me
1. Et&Cl
60% 2. BuZnCl , DMF * BuJ==i OH 5% C12Pd(PPh3)2 2 BuLi ,5h Ay, M.; Gulevich, Y.V.; Noda, Y. Tetrahedron Lett., 1993, 34, 1437 OH
. . Nenlshl,;
0
SnBu3
v
10h
Zhang, H-C.; Brakta, M.; DavesJr,. G.D, Tetrahedron
OTf
0
0
L&t., 1993, 34, 1571
, 30°C, 91h 58% 87%ee,R
Pd(R-BINAP)2, PhH ProtonSponge C)zawa.F,; Kobatake,T.; wi.
Pi0
x
T, Tetrahedron Lett., 1993, 34, 2505
Q-I 11I, AIBN , To1 52%
46h, 85OC
SnBu3 Kinnev. W.A, Tetrahedron Lett., 1993, 34, 2715 PhBr , To1,2% Pd(PPh& phm,, Bu$nmNI-12 R.J&; Geng,B.; &Iore;ill. J.JE J. Org. Chem., 1993, 58, 1443 w-h7
00
w-b3
1. Me2SCHC02Et
H
Bu$n
B(W
l312
2. H202, NaOAc
Dem. M.-Z,; Li, N.-S.; Huanrr.Y.-Z,J. Org. Chem., 1993, 58, 1949
60%
47%
Compendium of Organic Synthetic Methods, Vo19
Section 74C
0
Br J&;
OMe
Qabar, M.N. J. Org. Chem., 1993,
58, 4473
1. PdC12 , LiCl , THF o”c + 25OC ] 2. aq. NH4Cl
-PhINH2
0
2. PhHgCl , O2 60% Larock. R.C%; Ding, S. J. Org. Chem., 1993,
E:z)
58, 2081
PhOTf , Pd(PPh3)4, 85OC
(CH2)8co2Me
/9-BBN
/
(74:26
&PO4 , dioxane
-
ph-
58,
2201
(cH2)&02Me 87%
Oh-e, T.; &G\raura. N.: Suzuki. A, J. Org. Chem., 1993, Ph
1.2 Et$n , 1.5% PdC12(dppf), THF 2. CuCN.2 LiCl 3.
Stadmiiller, Sot., 1993,
C02Et
H.; Lentz, R.; Tucker, C.E.; S tiidemann, T.; Diirner, W.; Knochel. 115, 7027
phi
3 eq. EtMgBr , Cp$rCl2 THF,rt,6h
Suzuki, N.; Kondakov,
D.Y.; Takahashi,
T, J. Am. Chem. Sot., 1993, 11.5, 8485
J. Am. Chem.
Section 74C
Alkylation of Alkenes
79
C02Et N2+BFd
4
C02Et
, EtOH
2% Pd(OAc)z , 60°C, lh
SenguPta.;
Bhattacharyya, OH
71%
S. J. Chem. Sot., Perkin Trans. l., 1993, 1943 OH
5 eq. MeMgBr 0.05 PdC12(PPh3)2
97% VW,;
Giesen, V.; Fuest, M. Liebigs Ann. Chem., 1993, 629
e, , DMF , Et&104 47% Ni(teta)(ClO& Ozaki. S,; Horiguchi,
I.; Matsushita, H.; Ohmori, H. Tetrahedron
Lett., 1994, 35, 725 iMe
LDA, TMS-Cl C3H
06
Et Wright. S.W, Tetrahedron
THF , -78OC
*
C3H
Et
93%
Lett., 1994, 35, 1841 Phi , Bu4NHS04,
aq. MeOH
02Me
02Me 5% [Pd(OAc)2/2 PPh3] Jeffery. T, Tetrahedron
A Ph
96%
Heck reaction in aqueous media Lett., 1994, 35, 3051
0
0
Phi , SmIz/THF , 15 min DMSO
0 Nazareno, M.A.; Rossi. R.A, Tetrahedron
Ph A/ Lett., 1994, 35, 5185
Ph
47%
Compendium
of Organic Synthetic Methods, Vol9
Section 74C
Ph Pd(OAc)2, Bu3P, 3h IS2CO3 , DMF , 80°C +
Phi
Ph +
quant. (78 Ono, IS.; Fugami, K.; Tanaka, S.; Tamaru. Y, Tetrahedron Lett., 1994, 0
I
Majetich.
OOCNHMe 6) 35, 4133
0 2 AlEt
, 0°C b
SPh
10h
G,; Zhang, Y.; Liu, S. Tetrahedron
SPh
I
0 Lett., 1994,
4 35,4887
0
70%
,SnBuj
Pd(PPh3)4, THF ,65OC, lh Matthews,
D.P.; Waid, P.P.; Sabol. J.S.: McCarthy. J.R, Tetrahedron
66% Lett., 1994, 35, 5177
TfO OMe
SnBu3
OMe 70%
B.
D,; Cardamone, Rbe9 Guzzi, U. Tetrahedron l
/ SnBu3 1. 5% Pd2(dba)3 ,20% AsPh3 w 2.5% TFA , CH2C12 = Rink amide resin Deshnande. M.S, Tetrahedron
Lett., 1994, 35, 5613
89%
Section 74C
81
Alkylation of Alkenes
2 eq. MesSiCHzMgCl
phwseMe
b l?h-siMe3 5% NiC12(PPh&, DME reflux , 1.5h Hevesi.L,; Hermans,B.; Allard, C. Tetrahedron Left., 1994, 35, 6729 1.0.3 q3-C3HSPdC1)2 , HSiPh2F 0.6 o’-diphenylphosphinobinaphthol Ph-
79%
Ph
derivative
P
20°C , 10h 2. MeLi
Me S iPh2Me
96% (66%ee,S) Hatanaka. Y,; Goda, K.; Yamashita, F.; Hiyama, T. Tetrahedron
NC
/‘Q
Left., 1994, 35, 7981
0
NH 12
NH2
Mn(OAc), , CuOAc ultrasound ,4h
/ Bosman, C.; D’Annibale.
0
47%
A.; Resta,S.; Trorrolo.C, Tetrahedron Bufl+
Left., 1994, 35, 8049
(Ph3SnF2)‘, THF
OTf
Ph Pd(PPh3)4, reflux ,30 min
-
8-
81% A.&; Barcina, J.O.; Cerezo, A. de F.; Subramanian, L.R. Synlett, 1994, 1047
10% ZrC12(qC&),
1.5 BuMgCl
II, 6h Takahashi. T,; Kotora, M.; Kasai, K. J. Chem. Sot. Chem. Commun., 1994, 2693 ,SiUe3 1. BuLi , THF , -7OOC 2.ZnBr2, -7OOC + 2o”c 3. H30+
t
81%
82
Section 74C
Compendium of Organic Synthetic Methods, Vol9
C$-I&Me#H
, Et3SiH
t
AcH$(H$)4\/
SW3
tridecane , di-t-Bu hyponitrite 65% Dang, H.-S.; Roberts,.P,
Tetrahedron
Lett., 1995, 36, 2875
PhSnCl3, aq. KOH ,3% PdC12 *
Br*COOH
Ph*COOH 83%
Rai, R.; Aubrecht, K.B.; Collum. D.B. Tetrahedron
Lett., 1995, 36, 3169
cylization-Diels-Alder
Joumet, M.; B.
m J. Org. Chem., 1995, 60, 6885
Chavan. S.P,; Ethiraj, KS. Tetrahedron
Lett., 1995, 36, 2281
OMe
OMe BF3eOEt2, C&I 12, refk
y 2h
56% Maietich.
G,; Liu, S.; Siesel, D. Tetrahedron
Lett., 1995, 36, 4749
Alkylation
section 74C
83
of Alkenes
Ph 10% Pd(OAc)z ,20% Bu3P Phi , DMF, 100°C, 1Sh
S.-K,; Jung, K.-Y.; Park, C.-H.; Namkoong, E.-Y.; Kim, T.-H. Tetrahedron
Zhang, W.; Dowd. P, Tetrahedron
Lett., 1995,
Lett., 1995, 36, 8539
95% Yu, J.; Cho, H.S.; Falck.
Tetrahedron
Lett., 1995, 36, 8577
. JEt3
, PhMe , reflux
5% RuH2(CO)(PPh& 94% Trost.;
Ixni, K.; Davies, I.W. J. Am. Chem. Sot., 1995, 117, 5371 1. Me3Al,8%
y”
Cl$ZrCpz , DCE ,22OC
2.02 92% (74% ee)
Kondakov,
D.Y.; Negishi.J.
Am. Chem. Sot., 1995, 117, 10771
Compendium of OrganicSyntheticMethods,Vol9
84
4
OTf
Draper,T.L.; mv.
Section74D
CO,Et
,5% PdC12(PPh3)2 w 3 LiCl , DMF , 110°C
T&SynZett, 1995, 157 Si(OEt)g
Si(OEth
, toluene,135OC
0
0
Ru(H)2(CO)(PPh&7 2d
%
c
50% Kakiuchi, F.; Tanaka,Y.; Sato,T.; Chatani,N.; Murai. S, Chem. Lett., 1995,
679
1. BC13, CH2C12,O°C PhwPh 2. catechol, PhH 3. PhBr, Pd(PPh& , NaOH Farinola,G.M.; Fiandanese, V.; Mazzone,L.; Naso.F, J. Chem. Sot. Chem. Commun., ph-sMe3
86% 1995,
2523 REVIEW:
“RecentDevelopments andNew Perspectives In The HeckReaction,”Cabri.W,; Candiani,T. Accts. Chem. Res., 1995,
SECTION
74D:
28, 2
Conjugate Reduction of a&Unsaturated Carbonyl Compounds and Nitriles
0
0
2% [Pd(Pt-Bu)(PHt-Bu& 02 9 H2(10 psi) I 4
Me
90%
THFJ3h glassautoclave )
Sommovigo,M.; u.H.Tetrahedron
Lett., 1993,
4
Me
34, 59
OH Eta-
9 ~&oh6
t
ph/\/co2ph
CO (1 atm), NE@,3O”C 80%
bh. x; Fujiwara,IS.; Takahashi,S. Bull. Chem. Sot. Jpn., 1993, 66, 978
Section 74D
85
Conjugate Reduction
PhSiH3, 20°C, 16h MOcomplex
..
(62 Schmidt.T, Tetrahedron
38) 95%conversion
Lett., 1994, 35, 3513
NaHTe, EtOH Ph*CHO
w
phmCHO
rt ,5h
>98%
Yamashita.M,; Tanaka,Y.; Arita, A.; Nishida,M. J. org. Chem., 1994, 59, 350 TFA-Et3SiH,30 min -78°C + O°C
zhao, Y.; m.
variousprotonicandLewisacidsused P,; Keo, E.A. Tetrahedron Lett., 1994, 35, 4179
NH4+HC02-, Pd-C
t
25OC,4h
Ranu.B.C; Sarkar,A. Tetrahedron
Lett., 1994, 35, 8649
Bakersyeast, 31°C =, pheNo2 phmNo2 3d . shl&, M..; Yoshida,S.; Kohno,Y. Heterocycles, 1994,37, 553
43%
limonene, 10%Pd/C, reflux 0
o= von Holleben.M.L,; Zucolotto,M.; Zini, C.A.; Oliveira, E.R. Tetrahedron,
0
quant.
o=
6994, 50, 973
Compendium of Organic Synthetic Methods, Vol9
86
Na&Od
, aq. dioxane
,5O”C
PhA
, lh *
ECHO
Section 74E
Phi
ICI-IO selective
reduction
of conjugated
Dhillon. RS,; Singh, R.P.; Kaur, D. Tetrahedron
carbonyl C=C units L&t., 1995, 36, 1107
Sm, 12, MeOH , 1min t Bessho,K.; Yanada,K. Synlett,
a;
C02Me
ph/\/C02Et
97% 1995,
443
C02Me
BER-CuS04, MeOH, rt
BER = borohydrideexchangeresin Sim, T.B.; Yoon. N.M,SynZett,
1995,
94%
726
NaBHeBiC13,95%EtOH t
wC02Et Ren,P.-D.; Pan,S.-F.; Dong, T.-W.; Wu. S.-HJynth.
-
CO2Et 98%
Commun., 1995, 25, 3395
0
0
Bakersyeast
,; Saitou,K.; Hida,K.; Ohno,A. Tetrahedron
SECTION
Asymmetry, 1995, 6, 2143
74E: Conjugate Alkylations
Ranu. B.c; Saha,M.; Bhar, S. Tetrahedron
L&t., 1993, 34, 1989
Section 74E
Conjugate Alkylations
PhS-
b
0’ Li+
EL CH2C12 2d, -78OC
\ 6
‘t,
CO2Me
87
C02Me
6
SPh + 2
(15 Corey. E.J,; Houpis, I.N. Tetrahedron
Lett., 1993, 34, 24k
P 1. PhMgBr , CuBr*SMez
h Tv
2.NBS,THF,-78°C
*
0
Li, G.; Jarosinski,M.A.; J-In&y. V.J, Tetrahedron Lett., 1993, 34, 2565 0
PhguLi , THF , -78OC + TMSCl + TMSCN ; James,B. Tetrahedron
81% 83%-k
Ph
Lett., 1993, 34, 6689
h
3 eq.mSnBu3 0.05(Bu$n)z 6 eq.PhSCH(OMe)z 0.3 M PhH, hv (sunlamp)
ea
20%
Me
69%
OMe
(8: 1 transxis)
mk. G&; Kordik, C.P. Tetrahedron Lett., 1993, 34, 6875
I
1
Me(Boc)NCHzSnBu$s-BuLi TMEDA , CuCN, TI-IF
er. m;
Alexander,C.W. Synlett, 1993, 407
&
98% NMeBoc
Section 74E
Compendium of Organic Synthetic Methods, Vo19
88
Et
$
Et 9 Eu( tfc)3 MS , Ccl,, -33OC, 72h
-*
71% (25%ee)
Eu(tfc)3 = [tris-(3-trifluoromethylhydroxymethylene)-d-camphorato] europium (III) Tetrahedron L&t., 1993, 34, 7649 Bonadies, F.; Lattanzi, A.; Orelli, L.R.; Resci, S.; Screttri.
1. BnOCH~CH+CH/Cp$Zr(H)Cl 2. MeLi , Me$u(CN)Liz
81% rnshutz.R.H; Wood, M.R. J. Am. Chem. Sot., 1993, 115, 12625 0 -3
1. Ni(aca& 2. -w
80% Eshelby,J.J.; Crowley, P.J.; Parsons.P.J,Synlett, 1993, 279 1. Me2CuLieLiI
Bu
-
/-co2Et
*
2. MeOTf Amdt, S.; Handke,G.; Krause.N, Chem. Ber., 1993, 126,251
4
SO2Ph -
1. t-BuBr , Cr(en)2+2 , DMF ,4h * 2.H20
t-Bu \
78% \
en = ethylenediamine Tashtoush,H.I.; hstmann. R, Chem. Ber., 1993, 126, 1759
S02Ph
Section 74E
Conjugate AIkylations
89
Ph$b , cat. Pd(OAc);! 0
AgOAc , AcOH ,25OC
Cho, C.S.; Tanabe, K.; Uemura.
Tetrahedron
Ph
Lett., 1994,
0
1275
35,
41%
3 eq. SmI2,THF ,-78°C
Trivellas,A. Tetrahedron Lett., 1994, 35, 1627
-E.J.;
cat. Pd(OAc)z, NaOAc , Id cat. SbC13,AcOH ,25OC *
‘“\(‘rf
88%
0
Ph Cho, C.S.; Motofusa, S.; IJemura.S, Tetrahedron Lett., 1994, 35, 1739 r
0
Me02
3 eq.Me$iSnBu3,2 eq.CsF DMF,rt, lh Br Sate,H.; Isono,N.; Okamura,K.; Date,T.; Mori. M, Tetrahedron
Lett., 1994, 35, 2035
MeTi(OiPr)dMgCl , TI-IF Ni(acac)z, -15OC + rt
Bs.; 6075
.
85%
Kabbara,J.; Nickisch,K.; Neh, H.; Westermann, J. Tetrahedron Mt., 1994, 35,
90
Compendium of Organic Synthetic Methods, Vo19
Section 74E
t-BuHgCl , Et3SiH , DMSO ==c
) dark, hv (sunlamp) -35OC , llh Russell. G.A,; Shi, B.Z. Tetrahedron Lett., 1994, 35, 3841 C02Et
Et$i
A
C02Et 93%
iPrCH0, LiNO3, aq.MeCN e’ C02Me +QL 2 34% UT.; Soejima,T.; Takigawa,K.; Yamaguchi,Y.; Maekawa,H.; I(ashimura. S, Tetrahedron Lett., 1994, 35, 4161 Y
C02teBu 1. BuLi, m -100°C + 3o”c
,C02t-B :: = t =
2. H-20
u
70% +
otherisomers
CookeJr.. M.P,; Gopal,D. Tetrahedron
Lett., 1994, 35, 2837
PhCHO, Ph2C0 hv
Kraus.G.A,; Liu, P. Tetrahedron
69%
Lett., 1994, 35, 7723
MeMgCl , CeC13,THF
Bli.
G,; Bosco,M.; Sambri,L.; Marcantoni,E. Tetrahedron Lett., 1994, 35, 8651
Conjugate Alkylations
Section 74E
wey.
a, Hajra, S.; Ghorai, M.K. Tetrahedron
91
Lett., 1994,
35, 7837
MeO&
Bu$nH
COzMe
.
(1 Miura,
Iondo, T.; Hosomi. A, Tetrahedron
0
$
+
, PhH
BuC=CH , PhC=CSnEtj
Wl
W-I
11
1) 54%
Le ‘tt., 1;94,35,9605
, Me&Cl
Ni(acac)z , Dibal , THF , rt ,2h
%A
80% (>95:5 E.-Z) Ikeda, S.; &to.
Y, J. Am. Chem. Sot., 1994,
116,
5975 CHO
I
94% (93:7 1,4: 1,2) Kabbara. L; Flemming, S.; Nickisch, IS.; Neh, H.; Westermann, J. Synlett, 1994, 679 Et2Zn , MeCN , 1.5% NiC12 , -3OOC phL
ph
309’ chual pyrrolidine 0
l
*Phuh 75% (82% ee , S)
Asami. MJ Usui, K.; Higuchi, S.; Inoue, S. Chem. L&t., 1994,
297
Compendium
92
Ph
Section 74E
of Organic Synthetic Methods, Vol9
Z
Li
Y CH2CI;!
99% AI(OAr)3 , -78OC , lh
I
Ar = 2,5diphenylphenyl Maruoka,
Ph
K.; Shimada, I.; Imoto, H.; Yamamoto. H, Synlett, 1994, 519 PhMezSi
0 HSiPhMe2 , toluene , 1 10°C A
-N
*
[Rh2(oAc),l
dNJl
I I Bn Bn u T,; Oda, T.; Kimura, F.; Onishi, H.; Kanda, T.; I(;ito. S, J. Chem. Sm. Chem. Commun., 1994,2143 1. PhMe#Li ph&C02Me
Crump, R.A.N.C.; wing.;
87%
, Me$Zn , THF/toluene , O°C
2* aq* NH4C1
CO2Me
98% 73% using cuprate Urch, C.J. .I. Chem. Sot., Perkin Trans. l., 1994, 701
5% CuBr , THF , TMSCl ,4h AlMe
, 10% solution in hexane
96% Kabbara. J,; Flemming, S.; Nickisch, K.; Neh, H.; Westermann, J. Chem. Ber., 1994, 127, 1489 t-Bu
t-Bu (t-Bu)2Cu(CN)Li2
t-Bu w
C02Et Gerold, A.; .Krause. N, Chem. Ber., 1994, 127, 1547
quant. 111111111 \ CO2Et
Section 74E
Conjugate Alkylations
93
0
, DME ,0.3h
-A
C02Et
B
.
LiOH , Hz0
96% FJ Forcellese, M.L.; Locati, L.; Screttri, A.; Scolamiero, C. Guzz. Chim. Ital., 1994,
124,467
PhBr, NiBr2, e’ *
-/c”u
63%
phwco2Et
3 H20, DMF-Py , 80°C Bumr , Bu&I Condon-Guegnot&; Leonel,E.; N&l&ec, J.-Y.; P&ichon,J. J. Org. Chem., 1995, 60, 7684 OSiMe3
0 5 M LiClOd, ether
Sarawathy,V.G.; Sankararaman.J.
70% Org. Chem., 1995, 60, 5024
t-BuZnBr , THF/pentane, -3OC 2 TMSCl , 1.5BF3aEt2 Hanson,M.V.; Rieke,
J. Am. Chem. Sot., 1995, I 17, 10775
iPr1, Bu$nH , Yb(OTf)3
t
CH2Q/hexaneKHF . . Slbl. M&; Jasperse, C.P.; Ji, J. J. Am. Chem. Sot., 1995, II7, 10779 neatAl(C3H7)3,5% CuBr Ph& w;
Flemming,S.; Nickisch,K.; Neh, H.; Westermnn,J. Tetrahedron,
76% 1995, 51, 743
94
Section 74F
Compendium of Organic Synthetic Methods, Vo19
1. &D
,O”C,hv
2. LTA , PhH , heat
Barton, D.H.R.; Chem, C.-Y.; Jaszberenvi. JCs, Tetrahedron,
1995,
C02Me 98~25% 51, 1867
R.-S)
61%(80%ee;10:90
Wu, J.H.; Radinov, R.; Porter. N.A, J. Am. Chem. Sot., 1995, 117, 11029 REVIEW:
“Intramolecular MichaelandAnti-MichaelAdditionsto Carbon-Carbon Triple Bonds,”Rudorf, W.-D.; Schwarz,R. Synlett, 1993, 341 SECTION
74F:
Cyclopropanations, SO2Ph
including Halocyclopropanations
‘CH(SOMe)2,DMSO 99% 20°C, 15min
J-E,; Lofstom,C.; Juntunen,SK. Tetrahedron Lett., 1993, 34, 2007 N2CHC02t-Bu, CH2C12
/,%, + ,,\+\’A *,%, ‘Cod-Bu ‘h ‘C02t-B u . (86 . 14) 75% 92%ee Ito, K.; Katsuki.T, Tetrahedron Lett., 1993, 34, 2661 CuOTF-biarylamine ligand -,PP
C&I, CrCl$Fe
02Et C02Et
Hu. C-M.; Chen,J. Tetrahedron
Lett., 1993, 34, 5957
89%
Section 74F
Cyclopropanations
95
70%
\ Kreif. A; Dubois, P. Tetrahedron
Lett., 1993, 34, 2691
Ph
P Bu$nN(Et)CO2Me,DCE
(93:7 1,2-tranxcis) Shibata,I; Mori, Y.; Yamasaki,H.; Baba,A.; Matsuda,H. Tetrahedron Lett., 1993, 34, 6567
Ph
h
bis-Rh catalyst, styrene
t 0 . Davies.;
L4 = = Eo,?Me
63% Hutcheson,D.K. Tetrahedron
Ph +
9O%ee
Lett., 1993, 34, 7243
1.NBS, DMSO ,5 min ,,il/v/
::::;:H
*
p Kd’
Dechoux,L.; Ebel, M.; Jung,L.; Stembach.J.F, Tetrahedron
L”ToEt 10%Pd(PPh3)4,DMF ,7h
)
H g2%
(>99: 1 cis:trans)
Lett., 1993, 34, 7405
;
0 Ogoshi,S.; Morimoto, T.; Nishio, K.; Ohe, K.; Murai. S,J. Org. Chem., 1993, 58, 9
gg%
96
Compendium of Organic Synthetic Methods, Vol9
..
(97
.
Section 74F
3)
84%
avres.H.ML; Huby, N.J.S.; CantrellJr., W.R.; Olive, J.L. J. Am. Chem, Sot., 9468
1993,
115,
CrC12- DMF ,3h Bu
CHO 32%
Montgomery,D.; Reynolds,K.; Stevenson.P,J. Chem. Sot. Chem. Commun., SO2Ph
LiCH(SPh)S02Ph,THF
/
SPh
-78OC + O°C
t
1993,
363
PhS Isc-
81% Bailey, P.L.; Hewkin, C.T.; Clegg,W.; kkson. R.F.W, J. Chem. Sot., Perkin Trans. I., 1993,577
Me I
0-
C@Me
Na+%H(C02Me)2,TI-IF-HMPA -70OC + O°C ,3h
C02Me 63%
Watanabe,Y .; Ueno,Y .; m.
T, Bull. Chem. Sot. Jpn., 1993, 66, 2042 CH212,Zn , Et20 40°C, 8h Pb , Me$iCl
SK.;
Kakiuchi,T.; -0.
Ic J. Org. Chem., 1994, 59, 2671
97%
Section 74F
Cyclopropanations
97
PhS,
b @Ylr::~~~: 302Me Mac 50%
C02Me
Denis,R.C.; Gravel. D, Tetrahedron Lett.,
35, 4531
1994,
(2.7 OH
Bu$n ai
2 eq.Et@, CH& CH$lz-hexane, -2OOC NHSO&H,pNo,
0
BGn, -
%, /
#H ++
HA_
OH
+ NHS02-C6H4p-NO2
86%ee(2S,3R),94% Imai, N.; Sakamoto,K.; Takahashi,H.; Kobavashi,S, Tetrahedron Lett., 1994, 35, 7045 1. PhCHN2 2. PhCH=CHz, rt , 12h
cp\ OC-Fe/ oc
-4
Seitz, W.J.; Hossain.M.M, Tetrahedron
80% (96:4 cixtrans) Lett., 1994, 35, 7561
MezN
Ph
&pNMe2 + “)7
1. PheOH
Ph
0\/
0 B Bu
w PhvOH
2.2.2 Zn(CH21)2 >95%(29:1)
Charette.A.B,; Juteau,H. J. Am. Chem, Sot., 1994, 116, 2651 Et$n , CH212,CH& hexane, -2OOC
Ph a
Ph-oH
Hs s: a H
,SO,Ph
OH
N\ ,B-iBu N ‘SO
quant.(76%ee) Ph
Imai, N.; Takahashi,11.;Kobayashi.S, Chem. Lett.,‘1994,
177
98
Compendium
of Organic Synthetic Methods, Vo19
Section 74F
Ph Ph ’ Br
Ph
Bu2Te@mSiMe
3
0 +
C&03, 7o”c DME , trace water
Ph
Me3Si
Y.-z;
..
8) 93% MesSi Tang, Y .; Zhou, Z.-L.; Xia, W.; Shi, L.-P. J. Chem. Sot., Perkin Trans. I .,
1994,893
3-pentanone/LDA ,
THF
*
S02Ph Ericsson, A.M.; Plobeck, N.A.; mkvall.
62% J.-E. Acta Chem. Stand. B., 1994, 48, 252
Zn ClMe2SiCH$H$iMe2Cl
Mo(.herwell.
W.B,; Roberts, L.R. Tetrahedron
L&t., 1995, 36, 1121
2 Ti(OiPr)d 4 iPrMgBr -45OC +
0°C 93% (58:42
Kasatkin, A.; Sate.
PhaOH
Tetrahedron
Lat., 1995,
36,
trans:cis)
6079
l.Zn(CH$)2 2. -78OC -+ -2OOC 3. TiQ
*
ph-YoH 90%
Charette.,
Brochu, C. J. Am. Chem. Sot., 1995,
117, 11367
Section 75
Alkyls from Misc.
99
5% semi-corrin Cu complex , DCE 23OC
57% (95% ee) Pique, C.; Fahndrich, B.; pfaltz. A, Synlett, 1995, 49 1 1. XX12 , CC14, reflux 2. NaI04 , 0.1 RuC13
85%
3. Li 5% DTBB , THF 4. H20 Guijarro, D.; Yus. w Tetrahedron,
Ar
Ar = 4- t-bu tylphenyl 1995, 51, 11445
REVIEW:
“The AsymmetricCyclopropanantion of Acyclic Allylic Alcohols:Efficient Stereocontrol with IodomethylzincReagents,”w. A&; Marcoux, J.-F. Synlett, 1995, 1197
SECTION
75:
ALKYLS, METHYLENES AND ARYLS MISCELLANEOUS COMPOUNDS
~co2MhMe#-~-~~2~(OAc)~
as.
.
LEMe
Y,; Planchenault, D.; Weber,V. Tetrahedron Lett., 1994, 35, 9549
SOzt-Bu
FROM
73%
Ph
2 PhMgBr,5% NiC12(PPh&
77%
Clayden,J.; Cooney,J.J.A.; Julia. M cJ. Chem. Sot., Perkin Trans. 1.) 1995, 7 REVIEW:
“OrganonickelChemistryin OrganicSynthesis.SomeApplicationsof Alkyl and MetalacyclicDerivatives,”C&npora,J.; Paneque, M.; Poveda,M.L.; Carmona.E. Synlett, 1994,465
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
100
Compendium of Organic Synthetic Methods, Vol9
CHAPTER
6
PREPARATION
SECTION
Section 77
OF AMIDES
76: AMIDES
FROM ALKYNES 0.3 Iu1&0)16, co, Hz0 dioxane , NEt3 , 175OC Ph Ph
Hirao, K.; Morii, N.; Joh, T.; Takahashl. . S, Tetrahedron
SECTION
77: AMIDES
FROM ACID DERIVATIVES 1. SnFJ(TMS)2]2
OH Bumell-Curty,
2.
C
C.; lXosw Tick,
Lett., 1995, 36, 6243
, THF , rt Pa
NNH
‘N
7 14h
a
89%
Tetrahedron
Lett., 1993, 34, 5193
Li , Me3SiCl CsF’N2
)
+
pANH
iplq.ll
2
Kawaguchi,
C&I17NH2, W-J
17CWH
0
180°C, 30 min t C8h
. SIC. B&;
H
77% M.; Hamaoka, S.; Mori. M. Tetrahedron L&t., 1993, 34, 6907
NHC8H17
98% Zdravkovski,
2. Synth. Commun., 1993, 23, 2761
11%
Section 78
Amides from Alcohols
101
Cl
Ph
NMM , PhCl , mrcrowave *
f
N\
75OC ,2 min
Me
.
(20 Bose, AK.; Banik, B.K.; Manhas. MS, Tetrahedron
80) no yield
Lett., 1995, 36, 213 Ph
PhCH-NPh , toluene , Bufl 40% (5:95 cis:trans) Ph Browne, M.; Burnett, D.A.; Caplen, M.A.p; Chen, L.-Y.; Clader, J.W.; Domalski, M.; Dugar, S.; Pushpavanam, P.; Sher, R.; Vaccaro. W,; Viziano, M.; Zhao, H. Tetrahedron Lett., 1995, 36,2555 -C02H
,CWl;!
‘z ;;iPPb
. Frayen. P,Synth.
t
bCONHBn
2
98%
Commun., 1995, 25, 959 1. NsCl , NEt3 , DMAP/MeCN
, rt
0
+
PhCOOH 2. PhNH;! , rt
NHPh
Is,e. JC,; Cho, Y.H.; Lee, H.K.; Cho, S.H. Synth.Commun.,
SECTION
78: AMIDES OH
FROM
ALCOHOLS
1995, 25, 2877
AND THIOLS
CoC12, Ac20, MeCN *
Mukhopadhyay,
M.; Reddy, M.M.; Maikap, G.C.; w.
-(=)-/OH
MeCN , BFyOEt2
Firouzabadi.
LNHAc
J, J. Org. Chem., 1995, 60, 2670
w-
H,; Sardarian, A.R.; Badparva, H. Synth. Commun., 1994, 24, 601
92%
102
Section 81
Compendium of Organic Synthetic Methods, Vol9
SECTION
79: AMIDES
FROM
ALDEHYDES
NO ADDITIONAL EXAMPLES
SECTION
80:
AMIDES ARYLS
‘-(=)
FROM
ALKYLS,
PPA , AcOH , NH20H*HCl
METHYLENES
AND
‘-0
*
llO°C , 14h
80% Cablewski,T.; Gurr, P.A.; Raner,K.D.; S
SECTION
81: AMIDES
FROM
Org. Chem., 1994, 59, 5814
C&J.
AMIDES
Conjugate reductions of unsaturated amides are listed in Section 74D (Alkyls from Alkenes).
oJ-q// 1,,,,,,, A H
Wei, Z-Y.; Knaus.
Tetrahedron
Lett., 1993, 34, 4439
2.1 TBSOTf ,23OC 4.2 NEt3 , 1.75h
Ph J
R *
N/ I
Phd/Me
Me 75%
2.1 TBSOTf ,23OC 4.2 collidine ,2h
&&
91% (>99%ee)
MeOH
H
Ph
J 49%
G.E.; McHardey,S.F.; Murry, J.A. Tetrahedron
PhI(OAc)2,
A! I
KOH
N/
Me
I
cH2oTBs
Lett., 1993, 34,6215
72% NHCO2Me
Vaid, R.K.; P&ash, 0.; Tuladhar,SM. J. Org. Chem.,
Section 81
Amides from Amides
PhMgBr , THF
OEt H Wei, Z.Y.; Knaus.
A
Ph
103
H
78%
Org. Prep. Proceed. Int., 1993, 25, 255
1. 2 eq. s-BuLi, (-)-sparteine NHMe 2. Me1
Beak. P,; Du, H. J. Am. Chem. Sot.,
1
NHMe 84%(78%ee)
1993,
115, 2516
0
4.2 eq.CuBrz*LiOt-Bu
77%
*
Ph rt ,6h NH2 Yamaguchi,J.; Hoshi,K.; Qkgla. T, Chem. Lett.,
5) c>, 0
1993,
PhHNJL
Ot-Bu
1273
, acetone, O°C
CL N N 0 I I H OH Nesct,S.M.; Benneche,T.; Undheim,K. Acta Chem. Scand. B., 1993, 47,
71% 0 1141
CF3S03H, CH2C12 H
0.75h , 20°C
m
C.&l,; Fallah,A. Tetrahedron
&-H
Lett., 1994, 35, 293
DkE
*
4-K;
DIAD = diisopropylazodicarboxylate 0 Ww.
M.A. Tetrahedron
Lett., 1994, 35,665
91% (+ 4% lactone)
104
Compendium
of Organic Synthetic Methods, Vol9
Section 8 1
1. Br;! 2. NEt3 3. BnNH2
n B N
4. Mg(OMe)z
tier.
P,; Dogan, 0.; Pillai, S. Tetrahedron
H
Lett., 1994, 35, 1653
Axon, J.; Boiteau, L.; Boivin, J.; Forbes, J.E.; md.
Hoffman.V,; 35,323l
(s)
*Y 86x79%
1. (PhCO)zO , PhH , reflux 2. Bu$nH , AIBN , PhH
BnI-IN
P
, MeOH
02Me
Me
67%x”high yield” Lett., 1994, 35, 1719
SZ, Tetrahedron
iPrOH , 80°C, lh
d I OTf Nayyar, N.K.; Shankweiler,
CH20iPr 85%
J.M.; Klinekole
H III, B.W. Tetrahedron
C7H &HO, Hz, 40 bar Pd/C-Na2S04, EtOAc
0
0
1ooOC H Fache, F.; Jacquot, L.; J,eme.
Ph-NVCI
93%
w17
M, Tetrahedron
L&t., 1994, 35, 3313
s-BuLifIMEDA I Boc
Lett., 1994,
, THF
a
Ph 4
-78OC, 5h
Beak. P,; Wu, S.; Yum, E.K.; Jun, Y.M. J. Org. Chem., 1994, 59, 276
N I Boc
82%
Section 81
Amides from Amides
105
PhCHO , PPE , 60°C, 16h
H N’
51% * I PPE = polyphosphoric ester ci Ph Marson. CM,; Grabowska, U.; EaIlah, A.; WaIsgrove, T.; Eggleston, D.S.; Baures, P.W. J. Org. Chem., 1994, 59, 291 NH2
S Me N’
1. 1.3 eq. POC13,
-78OC
2.3.5 eq. TM&S
, -78OC +
Me N’ rt ,4h
91%
* c ei Smith, D.C.; Lee, S.W.; Fuchs. P.L, J. Org. Chem., 1994, 59, 348 0
0
BnNH2, AlC13 , 90°C >
NHBn
NH2
67% Bon, E.; Bigg. D.C.H.: Bertrand. G, J. Org. Chem., 1994, 59, 4035
yx N I
1.2 s-BuLi/2 TMEDA THF , -78OC, 8h Ot-Bu
2. BuI
CH3
Snieckus. V,; Rogers-Evans, M.; Beak. P,; Lee, WK.; 1994, 35, 4067
0 -Y
A N Ot-Bu I CH2Bu 70% Yum, E.K.; Freskos, J. Tetrahedron L&t.,
Bu$nH , cat. AIBN (addn over 4 h) degassed cyclohexane -
(Do
Ph Callier, A.-C.; Quiclet-Sire,
B.; Zard. S.2, Tetrahedron
66% Lett., 1994, 35, 6109
\
Me
106
Compendium of Organic Synthetic Methods, Vol9
Bu$nH,
Section 8 1
AIBN
PhH (OSM) Keusenkothen,
P.F.; Smith. M.B, J. Chem. Sot., Perkin Trans. I., 1994, 2485
Ts I N
iPrMgC1, THF , O°C ,6h
/\
4J4 *‘Ph
. . oshlmuu. 3465
. 57) 63% (45 A, ; Abe, H.; Hirosawa, C.; Tamao, K. J. Chem. Sot., Perkin Trans. I., 1994,
anek- E,; Wuonola,M.A.;
NH2
Harlow, R.L. J. Heterocyclic
65% x low yield Chem., 1994, 31, 1251 H I NN
1. B tCH20H
2. CH2=CHCH2SiMc3 BF3eOEt2 63% 0 R... menko. A.V.. . La n g. H, J. Org. Chem., 1995, 60, 4002
0
\ a V-bhBr OMe
I
/
N’ I
Bu$nH , AIBN , PhH reflux ,8h (syringe pump, 7h) *
~;~;NHco2Mx;:~ 2
co$k 30%
Lee.;
Whang,I-IS.; Chung,C.K. Tetrahedron
Mt.,
1995, 36, 913
360/ 0
co2M
Section 8 1
Amides from Amides
-L
(BnNEt&MoQ
107
, CHg12
82%
)
Ph
-78OC * rt ,30 min me2 Ilankumaran, P.; Ramesha, A.R.; Chandrasekaran. S, Tetrahedron L&t.,
me2
1995,
36, 8311
1.2.2 eq.BuLi , THF , -78OC+ 0°C 0 2.
0
Ph
N’
\
\ I d
NHMe 4
I
3. H30+ 4. Me$iCl , NaI , MeCN
/
WY. Pts, Tetrahedron
Lett., 1995,
/
Me
Ph
A
Ph 75%x92%
36,493
2 SnC12,2KI CH2C12 , rt , 12h N-(f6Hll
53% + 10%benzophenone Qmoka
T,; Iwama, T. Tetrahedron
Lett., 1995,
36, 5559
HC=CCH2Br,DMWDMF , NaH LiBr , O°C + rt THPO Liu, H.; Ko, S.-B.; Josien,H.; Curran.D.P, Tetrahedron
Lett., 1995,
36, 8917
Ph
Ph Ph
Mn(OAc), AcOH
D’Annibale,A.; Resta,S.; Trogolo,C. Tetrahedron
Lett., 1995,
36, 9039
87%
108
Compendium
42
of Organic Synthetic Methods, Vol9
Section 82
2% Rh#SMEPY)4 0
cwkt
N -b
Y Doyle. M.P,; Kalinin,
0
70% (96% ee)
cm2
A.V. Synlett, 1995, 1075 SPh
MeS
&SPh
neat, rt Id Ar = 4-methoxyphenyl
66%
Ar . x; Nakaharu, T.; Nishimura, M.; Nishikawa, A.; Kameoka, C.; Ikeda, M. Tetrahedron, m. . 1995, 51, 2929 Ph Bu$nH, Ph
I \
AIBN
Ph
*
+
toluenhe , reflux
Me bile
Me
47% 12% Sato, T.; Chono, N.; Ishibashi, H.; Ikeda. M, J. Chem. Sot., Perkin Trans. I., 1995, 1115
@O ,SO2Tol
Ph
Ph
Me$GCHC02Et
41%
N -7
-
. u-. UJt;
SECTION
b/ TolO# Arora, A. J. Chem. Sot., Perkin Trans. I., 1995, 2605
82: AMIDES
FROM
AMINES
NaB03a4 Hfi
P L -N-Ph Nongkunsam,
C02Me
, CF3C02H
80°C
P.; Ramsden. CA, Tetrahedron
+
H
Lett., 1993, 34, 6773
B
N \
/
Ph 51%
Ph
Section 82
Amides from Amines
109
0
NHBn
Sn[NUMS)212 9hexme 9fi CO2Me
C3H
pivalic acid
A
5r
C3H7
N\
P
Bn
89% Wang, W.-B.; w
J. Am. Chem. Sot., 1993, 115, 9417 NCCH2CH0,
c8H
17-NH2
Duetsch, J.; Niclas. H.-J,Synth.
r-t, 6h
) C&I 17-NHCH0 Commun., 1993, 23, 1561
78%
1. N-cyclohexyl-N’,N’,N”,N”tetramethylguanidine , pyridine toluene , CO2 , - 10°C 2. toluene , SOCl;! , -1OOC 77% McGhee. W.D.; Pan, Y.; Talley, J.J. Tetrahedron
1. 2eq.
Let?., 1994, 35, 835
R pkPhP Cl
3eqNEt3,THF
67%
-
2. excess NaH Osbom, H.M.I.; Cantrill, A.A.; Sweenev. J.B.; Howson, W. Tetrahedron
Let?., 1994, 35, 3159
xylene , 150°C, 3h NHBn -Gee.
c), N I Bn
0 93%
DLL; Ramaseshan, M. Synlett, 1994, 743
oc
NHBn
CO, MeCN Pd(PPh3)4, NBu3
OTf
Qiso. G.T,; Meyer, A.G. Tetrahedron,
quant. 1995, 51, 5585
110
Compendium of Organic Synthetic Methods, Vol9
C3H7wmt*
co 9w@w2
9dPPP )
Section 83
C3~7Aqqmt2 0
b&&&.
. S.-L; Imada, Y.; Nishimura, K. Tetrahedron,
SECTION
83: AMIDES
FROM
78%
1994, 50, 453
ESTERS ,0C02t-B u
H-N moAc
\
OCOzt-Bu
C02t-Bu
I
K2CO3, IT, Id
mNxC02t-Bu
77% . J-P,; Thorimbert,
S.; Touzin, A-M. Tetrahedron
L&t., 1993, 34, 1159
h
2 eq.Sn[NTMS2]2 2 eq.Me2NCH2CMe20H Ph-CO2Me
*
2 eq.PhCHMeNH2
dyA H
Wang,W.-B.; Restituyo, J.A.; Roskamo. E.J, Tetrahedron
Ph LA
0
1.5SnFJ(TMS)& , THF
0 OMe
97%
L&t., 1993, 34, 7217
*
1.5Et2NHaHCl,rt , 18h
Ph 3
mt2
52% Smith, L.A.; Wang, W.-B.; Burnell-Curty, C.; Roskamn.E.J, Synlett, 1993, 850 0
iPrNH2, t-BuOH ,1.5d 0-
Chen.S.-T; Chen,S.-Y.; Chen,S.-J. Tetrahedron 0 C3H
7A
*
25OC
I H
NaEtzAl(Bn)z, toluene OEt
reflux , lh
69%
Lett., 1994, 35, 3583
0 * C3H
72
NHBn 93%
Sim, T.B.; Yoon. N.M,SynZett,
1994, 827
Section 85
/ PMP
Amides Tom Halides
r
Ph
I N
)
111
(Lp+
]
(;p
2. NEt3 , CH2C12
PMP = 4-methoxyphenyl
. 30) 99% (70 Annunziata. R,; Benaglia, M.; Cinquini, M.; Cozzi, F.; Ponzini, F.; Rimondi, L. Tetrahedron, 1994, 50, 2939
0 A
1. BC13-SMe2 SPY
Ph/\i
p-l =-
Me
Ph
NMe2
74% (78%ee)
*
2. O*\
ph3N-PMP
PMP
PMP = N-4methoxyphenyl Annunziata,R.; Benaglia,M.; Cinauini.M.: Cozzi. F, Tetrahedron Lett., 1995, 36, 613
SECTION
84:
AMIDES FROM THIOETHERS
ETHERS,
EPOXIDES
AND
NO ADDITIONAL EXAMPLE!3
SECTION
85: AMIDES Br SiMe3
FROM
HALIDES
1.Mg
AND SULFONATES
m
2. PhNCO
83%
Co& Jr.. M.P,; Pollock, C.M. J. Org. Chem., 1993, 58,
-MgBr
c1’NMe2
+ bme2
cat. NiClz(dppe), THF vrt Babudri,F.; Fiandanese, V.; Marchese.G,; Punzi, A. Synlett,
1994,
719
90%
112
Compendium of Organic Synthetic Methods, Vo19
Section 87
1. CS2, THF PhMgBr
2. BtS02CF3
63%
w
3. BuNI&
. ~A.R.;
SECTION
Bt = benzotriazol-l-y1 Moutou, J.-L.; Yang, 2. Synlett, 1995, 99
86: AMIDES
FROM
NHBu
HYDRIDES
NO ADDITIONAL EXAMPLES
SECTION
87: AMIDES
FROM
Me02C-
aldehydes canalsobe used
KETONES
NH2
TEA, N~BH(OAC)~ DCE , rt ,45h
t
00-b 92%
bdel-Manid. A.F,; Harris,B.D.; Maryanoff, C.A. Synlett, 1994,81 OTIPS
1. 10eq.TMSN3 2 eq.PPTS CH2C12,rt ,2d 2. UV , 0°C , lh 79~89%
Evans. P.A%;Modi, D.P. J. Org. Chem., 1995, 60, 6662
Milligan, G.L.; Mossman,C.J.; Aube, J. J. Am. Chem. Sot., 1995, 117, 10449
1. NI$OSO3H, SiO2 2. Hz0 , microwave Laurent,A.; Jacquault,I?; Di Martino, J.-L.; Hamelin.J, J. Chem. Sot. Chem. Commun., 1995, 1101
Section 89
Amides from Alkenes
SECTION
88: AMIDES
FROM
113
NITRILES
UHP , cat. K2CO3 , aq. acetone N
PhCN
P
rt, lh
UHP = urea-hydrogen peroxide adduct Balicki. R,; Kaczmarek, L. Synth. Commun., 1993, 23, 3149 H
L
H
Mn02, SiO2, hexane
CN P Breuilles,P.; Leclerc,R.; m.
rt,lod
*
D, Tetrahedron
92%
Pu
Lett., 1994,
NH2
35,
1401 0
Al203 (neutral), 60°C, Id
70%
CN
t * w NH2 Wilgus,C.P.; Downing,S.; Militor, E.; Bains,S.; Pagni. R&k: Kabalka. GW, Tetrahedron Lett., 1995, 36, 3469
SECTION
89: AMIDES
FROM
ALKENES
TsN=IPh, Mn salencatalyst * PhA Ph pyridineN-oxide, MeCN , rt Noda, K.; Hosoya,N.; Irie, R.; Ito, Y.; Katsuki. T, Synktt, 1993, 469 1. PhI=NTs, Cu(OTf)2, MeCN e 2.0.1 M NaOH
Ts\
34%
N-Ts
N d-
77%
JCL; Muldowney, M.P. Synlett, 1995,949
SECTION
90:
AMIDES
FROM
MISCELLANEOUS
COMPOUNDS
BnN=C=O, hv (Pyrex filter) @
\
42% cr(m3
v. J.H.; Ahmed,G.; Ferguson,M.D. Tetrahedron
L&t., 1993,34, 5397
114
Section 90
Compendium of Organic Synthetic Methods, Vol9
o=
Bu&Re04,
N-OH
CF$03H,
MeNO
*
50% H2NOHaHCl
Narasaka, K.; Kusama, H.; Yamashita, Y.; Sato, H. Chem. Lett., 1993, 489
)iic,
T”Sy
v
+ a
2STMSOTf,CH; 7
202
n=
aux
,O,
Ph
Ph
Pouilhes,A.; Langlois.Y,; NshimyumuKiza, P.; Mbiya, K.; w.
30% (>95:5enbexo) 1,. Bull. Sot. Chim. Fr.,
1993, 130, 304
9\ //O
0\//
2. 1. MeMgCl BEt3 *
Ph’\
3. H2NOS03H Me Huane..-C,; Reinhard,E.J.; Reitz, D.B. Tetrahedron
0 50%
PhHs \ NH2
Mt., 1994, 35, 7201
hv , hexane, PhNMe2
ipmaJ( = 0.77 Post,A.J.; Nwaukwa,S.; Morrison. H, J. Am. Chem. Sot., 1994, 116, 6439
CO, MeOH, Pd(dpppK129PhH K2C03,160°C
NHCOzMe 59%
MeO$HN02N
Reddy,N.P.; Masdeu,A.M.; El Ali, B.; Alner. H, J. Chem. Sot. Chem. Commun., 1994, 863
Section 90A
Protection of Amides
Ph. 70 \
Mn(tpp)Cl
, MeCN
3o”c
0
115
Ph.
* P
0 60% tPP = tetraphenylporphyrin Suds. K,; Sashima, M.; Izutsu, M.; Hino, F. .I. Chem. Sot. Chem. Commun., 1994, 949 Montmorillonite
N-OH
K-10, microwave *
NHPh
7 min
Bosch, A.I.; de la Cruz, P.; Diez-Barra,
(17% with heating and no microwave) E.; Loupy, A.; Langa. F, Synlett, 1995, 1259
DMF , POC13, 90°C ,.
N-OH Majo, V.J.; Venugopal,
CHO
0 M.; Prince, A.A.M.;
N-OH
60% Perumal. P.T, Synth. Commun., 1995, 25, 3863 H N
0.2 Bu$lRe04,0.2 CF$OsH MeNO*, reflux ,0.5 NH~OH~HCl
Phx>”
0
CJ Ph Kusama, H.; Yamashita, Y.; Narasaka, K. BuZl. Chem. Sot. J’n., 1995, 68, 373
SECTION
*
90A:
PROTECTION
91%
OF AMIDES
0
0 0
2 Mn(OAc)3.2 H20, EtOH CU(OAC)~~H~O, 55OC 45%
N4
N4 \
SiMe3
OH Ghosh, A.; MiI&r. MuI Tetrahedron
L&t., 1993, 34, 83
\
H
SiMe3
116
Compendium
of Organic Synthetic Methods, Vol9
Section 90A
1. AlC13 ,6O”C 2. PhOMe ,6h
Kim, J.N.; Ryu. E.K, Tetrahedron
Mg(ClO&
Boc P Stafford.=; 7873
Lett., 1993, 34, 3567
99% 50°C ,20h * PA NHMe r’ Me Brackeen, M.F.; Karanewsky, D.S.; Valvano, N.L. Tetrahedron L&t., 1993, 34,
Mg(OMeh P
0
, MeCN
, MeOH
0
CO$-Bu Wei, Z.-Y.; Knaus.J Tetrahedron
P -
0 +
H
90%
Lett., 1994, 35, 545 5 eq. Ac20,4% 2.2 eq. Bu$nH
Pd(PPh& , CH2C12
NHOMe AcHN * G 58% o Roos, E.C.; BernaM, P.; Hiemstra, H.: Speckamp. W-N,; Kaptein, B.; Boesten, W.H.J. .I. Org. Chem., 1995, 60, 1733 rt , 10 min
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
Amines from Alcohols
Section 93
CHAPTER
7
PREPARATION
SECTION
91: AMINES
OF AMINES
FROM
ALKYNES
NO ADDITIONAL
SECTION
92: AMINES
\ox
SECTION
I
117
93: AMINES
FROM
ACID DERIVATIVES
NO ADDITIONAL
FROM 1. MeLi,
EXAMPLES
EXAMPLES
ALCOHOLS
AND THIOLS
THF
2. PhCN , warm OH Fitzgerald, J.J.; Michael, F.E.; Qlofson. R.A. Tetrahedron
(J-JPh
*
47%
/
L&t., 1994, 35, 9191 Me
1. BuN3, 2.5 eq. TfOH 95% 2. NaBH4 mn.
W.R,
Bu
Fang, W. J, Org. Chem., 1995, 60,496O PhCH2NHTf
, DEAD,
PPh3
PhCHzOH 93% Bell, K.E.; Knight. D.W; Gravestock, M.B. Tetrahedron
==c OH
Lett., 1995, 36, 8681
HNBn2, SnC12, NE@, THF ,2d
w NBn2
2% Pd(PPh3)4, 50°C
70% Masuvama.
Y.; Kagawa, M.; Kurusu, Y. Chem. L&t., 1995,
1121
Compendium of Organic Synthetic Methods, Vol9
118
SECTION
94: AMINES Me3S’
PhCHO
FROM
ALDEHYDES
-3
Me3SiCl ,29h
Jahn, U.; Schroth. W, Tetrahedron
(t
Section 94
Lett., 1993,
34, 5863
1. C$I 1lCHO , BER , EtOH NH2
Et3NHCl 2. BER , NaOH
* o-
NHCH2C5H1 l
BER = borohydride exchange resin Yoon. N.M.; Kim, E.G.; Son, H.S.; Choi, J. Synth. Commun., 1993, 23, 1595 LiAl(NHBn)d,
89%
ether
25OC, 7h Solladie-Cavallo.
A,; Bencheqroun,
M.; Bonne, F. Synth. Commun., 1993,
23,
1683
1. Bzt-SNH2 , NaOH , EtOH 2. PhSN(TMQ, cat. TBAF , THF Ph
3. Bu$nH
-?B&in,
, cat. AIBN , cyclohexane
CHO
61x69%
J.; Fouquet, E.; Zard. SZ, Tetrahedron,
1994, 50, 1745
1. Me2NH*HCl, Ti(OiPr), EtOH ,25OC, 10h
, NEt3 *
ph-CHO 2. NaBH4,25OC Bhattacharvva,
PhCHO
S, .I. Org. Chem., 1995,
Phw
NMe2
, 10h
95%
60,4928
1. BnNH2, PyeBH3, MeOH MS 481,16h
>
Ph/\N-Ph
2.6NHCl 3.8 N NaOH Bomann, M.D.; Guch, I.C.; DiMare. M, J. Org. Chem., 1995, 60, 5995 TsNH2, Si(OEt), , 160°C, 6h > PhCHO Love. BE; Raje, P.S.; Williams II, T.C. Synlett, 1994, 493
PhCH=NTs
I H
87%
68%
Section 96
119
Amines from Amides
BnNH2 , Bentonite , rt ,3h
PhCHO
w
80%
PhCH=N-Bn
ketones can also be used Saoudi, A.; Benguedach, A.; Benhaoua. H, Synth. Commun., 1995,25,2349 Related Methods: Section 102 (Amines from Ketones)
SECTION
95:
AMINES ARYLS
FROM
ALKYLS,
METHYLENES
AND
NO ADDITIONAL EXAMPLES
SECTION
96: AMINES
FROM
AMIDES
C6Hl3
Fisher, G.B.; Fuller, J.C.; Harrison, J.; Goralski, C.T.; Sin Tetrahedron Lett., 1993, 34, 1091
R,
KH , THF , Cp2ZrHC1
JyClOH21 t
PhJL
-2OOC + rt
PlrJ
NwoH21
86%
Schedler, D.J.A.; Godfrey, A.G.; Ganem, B, Tetrahedron Lett., 1993, 34, 5035 1. LiHMDS ; BnBr 2. LiHMDS ; Me1 3. LiA1H4 4. H2, Pd-C
G? Ph 0 Westrum, L.J.; Meyers. A& Tetrahedron
+ H’ 89%
Lett., 1994, 35, 973
Ph Tic13 ,3 eq. CsK Ph
Fs
90% H A; Hupperts, A.; Ptock, A.; Janssen, E. J. Org. Chem., 1995, 60, 5215
H
120
Section 97
Compendium of Organic Synthetic Methods, Vol9
0
A
HBr ,163OC
*
N
H-Nw-ph
NI-IPheHBr
L-l
88% Poindexter. Cr.&; Bruce, M.A.; LeBoulluec, K.L.; Monkovic, I. Tetrahedron L&t., 7331 /sWF3
1994,
35,
t-BuLi , THF , -60°C, 3h t-Bu
52% Bozee-Ogor, S.; SaIou-Guiziou, V.; Yaouanc, J.J.; Handel. H, Tetrahedron L&t., 1995, 36, 6063 Ph 3 Ti (powder), THF, 21h 3 TMSCl , reflux
t
Ph
AN-(
Ph
I
H r. pL; Hupperts, A. J. Am. Chem. Sot.,
1995,
117,
4468
H I
N
S
30%H202, AcOH, 25OC w
Me Grivas, S.; Ronne, E. Acta Chem. Scand. B.,
1995,
49,
H n-
N \
Me
85%
225
Related Methods: Section 105A (Protection of Amines)
SECTION
97: AMINES
c
N -Ph
AImena, J.; Foubelo, F.; m
FROM
AMINES
1.5 Li (powder) , TI-IF cat. CteHs , -78OC, 6h 2.H20 M, Tetrahedron
* vNHPh 93%
Lett., 1993, 34, 1649
Section 97
Amines from Amines
PhCHO , TFA
Me \ H
121
Et$iH , CH2C12, O°C
83%
\ H
Appleton, J.E.; Dack, K.N.; Green, A.D.; Steele. J, Tetrahedron
L&t., 1993, 34, 1529
9-BBN , THF ,20h *
Wy-”
56%
H ‘Ar Ar = 3,4-dimethoxyphenyl Gaul, M.D.; Fowler, K.W.; Grieco. P.A, Tetrahedron L&t., 1993, 34, 3099
70%
2. H30+ Maye, J.P.; Nerrishi. E. Tetrahedron
L&t., 1993, 34, 3359
?h
Ph
\ I/ 0 h
A
T
A 10 eq. MeLi, PhH ,5O”C w-
I v H’
I v
+
I-Y
N
NH2
Y >60% Genin, M.J.; Biles, C.; Romero&D.L, Tetrahedron
0
Mt.,
20% 1993, 34, 4301
1. s-BuLi , TMEDA 2. Me1
3. s-BuLi, TMEDA * Mz&’cx N 4. Me1 I Boc I&&. P,; Lee, WK. J. Org. Chem., 1993, 58, 1109
62x41% N
I Boc
Me
122
Compendium
9
of Organic Synthetic Methods, Vol9
Section 97
t-Bu 1.1.5 LDA, THF , O°C 62%
THF, 15h , O°C + rt 3.3 eq. K2CO3, MeOH heat, 3h N.G,; Keppens, M.A.; Stevens, C.V. Tetrahedron
Lett., 1993, 34,4693
2.5 eq. LiBHEt3 , THF , rt 84% (1:l cixtrans) Blough, B.E.; Carroll, F.I. Tetrahedron
0
N
I H Kanth, J.V.B.; Pemv.
\aI/
NH2
H L&t., 1993, 34, 7239
2.PhBr,THF,rt,6h l.Li,THF 3. MeOH ; 20% HCl MJ.
)
-
0
86%
N I Ph
Org. Chem., 1993, 58, 3156 H I
5% Pd(OAc)2, 5% PPh3 100°C ,3.5d, Na2CO3 +65, ’ * Larock. R.C,; Berrios-Pefia, N.G.; Fried, C.A.; Yum, E.K.; Tu, C.; Leong,W. J. Org. Chem., 1993, 58, 4509 I
ONMe
1. w&r<
, Me3COCl Me
2. To1 , 120°C, 20h
!&de&erg,
t
Me
65x60% H B.C.; Helton, E.S.; Austin, L.R.; Odens, H.H. J. Org. Chem., 1993, 58, 5589
Amines from Amines
Section 97
n
Ph
\
80 psig Hz, cat. Tl complex
*
65OC, 7h
N
Willoughby, C.A.; Buchwald. S.L, J. Org. Chem.,
123
84%
Ph/o
(99% ee)
N I
iI
1993,
58,
7627
acetone, NaBH4,3M H2SO4 , THF
w PhNHiPr Verardo, G.; Giumanini. A.G,; Strazzolini, P.; Poiana, M. Synthesis, 1993, 121
95%
pm2
OEt
0
BF4-
Sheu, J.; Smith. ML;
1. styrene , MeN02, reflux
Ph t
39%
2. NaBH4, EtOH Matsumoto, K. Synth. Commun.,
6
1993,
23,
253
SmI2,28 H20, THF
95%
rt,90min hr.. Y,; Kudo, T. Heterocycles, 1993, 36, 2383
H
Bu$nH, cat. AIBN cyclohexane Ph P
additon over 4 h
0 Boivin, J.; Schiano, A.-M.; ad.
S.Z, Tetrahedron
Lett., 1994, 35, 249
Na&O&$Q-Hz0 toluene , 1OOOC,15h 80%
Wong, Y.-S.; -0.
the reaction fails for many N-R where R # Bn c; Gnecco, D.; Das, B.C. Tetrahedron Lett., 1994, 35, 707
124
Compendium of Organic Synthetic Methods, Vol9
N-t-Bu
Section 97
1. Br2 , CH2C12 , 0°C 2.2 eq. LiAlH4, ether 78% t-Bu
DeKimpe, N.; Boelens, M.; Piqueur, J.; Baele, J. Tetrahedron
c-
s
1. (HCHO), , Ti(OiPr)J H 2. NaBH4 Tetrahedron
Lett., 1994, 35, 2401
Lett., 1994, 35, 1925
-C
-Me
95%
l.MeMgCl,THF,rt 2. Cp$rC12, THF 3. hexane/dioxane, rt 4. MeMgCl , -3OOC+ rt 5. MeOH Harris, M.C.J.; Whi&y. u;
*
Blagg, J. Tetrahedron
ph\/ Lett., 1994,
Ph 35, 2431
78%
Me
(10 Stevens, E.P. Tetrahedron
Pearson.;
2; 1994,
Lett., 1994, 35, 2641
McIntosh, J.; boon,
.
1)
’
J.M.; Hammaker, J. Tetrahedron
Lett.,
35,4899
Barnbridge,
1) 47% (6 K.; Begley, M.J.; Simpkins. N.S, Tetrahedron Mt., 19% 35, 3391
88%
Section 97
Amines from Amines
I2
125
:z;z~ cc&&$ 90%
Grellier, M.; Pfeffer. MJ van Koten, G. Tetrahedron
Lett., 1994,
2877
35,
N-t-Bu N-t-Bu
3 eq. LDA , THF, rt , 16h
I +
Stevens, C.V.;
; Katritzky, A.R. Tetrahedron
N
x
55%
d Lett., 1994,
3763
35,
LiEtzNBH3, THF , O°C Ph
Ph
lh
PhA PhA Fuller, J.C.; Belisle, CM.; Goralski, CT.; Singuam. B, Tetrahedron
95%
,,\w\H
(66% de) Lett., 1994,
35, 5389
PhSe I
Bu$nH
/\ N
, AIBN , PhMe a
N I Ph Ph 56% H Bowman. W.R,; Stephenson, P.T.; Terrett, N.K.; Young, A.R. Tetrahedron Lett., 1994, 35, 6369 addn via syringe pump
0.05 Prfl
Ru04 , 1.5 N-MO
MeCN,rt,
Goti. & Romani, M. Tetrahedron
Id
Lett., 1994,
35, 6567
Br N4 .
e m=
NaBH4, MeOH , heat
A?
L
Ph1 N.; De Smaele, D. Tetrahedron
N
Lett., 1994, 35, 8023
89%
Ph
126
Compendium of Organic Synthetic Methods, Vol9
0
5% chiral Ti catalyst, Hz, THF , rt
N
-0
Section 97
N I
75% (92%
3
Lee, N.E.; Buchwald. SL, J. Am. Chem. Sot.,
1994,
wk.
Ph\ 5985
116,
2 MeLi, toluene , -78OC
== = PhbMe
S&; Nakajima, N.; Nicaise, O.J.-C. J. Am. Chem. Sot.,
90% (70% ee 1994,
Bn\
1. Cp2ZrBu2, THF, -78OC Bn-N-
ee, R)
9w
116, 8797
N
2. aq. MeOH *
13i70%
Kemp, MI.; Whitby. R.J,; Coote, S.J. SynZelt, 1994, 451
,OMe N
1.
Ph:llll (.+/
fH
CPh20H
BH3GMe2 2. workup
(10%)
-
el++ / PI%
NHOMe
68% (50% ee , S)
Balm. C,; Felder, M. Synleff, 1994, 655
Ph
1. Bu$nH , AXBN, THF syringe pump, reflux +
r ‘-% PhS
Bowman.
WR;
;’ . ;; ;f;H 49% (2.8 : 1.2 : 1 (minor product) Clark, D.N.; Marmon, R.J. Tetrahedron, 1994, 50, 1295
Section 97
Amines from Amines
c
127
1. DCE , ClCO,Et -Bn
N-H
2. PhNEtpBI3
-
c 80%
Kanth, J.V.B.; Reddy, Ch.K.; Periasamv, M,Synth. Commun., 1994,
24,
313
1. (HCHO), , &Cl;!, THF 2.Zn(BH& , THE;, 25OC , 10h mNHMe
3. aq. NH3
70%
-s.;
Chatterjee, A.; Duttachowdhury, SK. J. Chem. Sot., Perkin Trans, I., 1994, 1
pL
l.NCS,PhH Me
NHMe
w 2. Bu$nH , AIBN , PhH , reflux
ph”\@
Tokuda, M,; Fujita, H.; Surrinome. H, J. Chem. Sot., Perkin Trans. I.,
A. I Me
1994,
Me 42%
777
,48% HBr * dioxane , sealed tube 100°C, 4d 78% &ge. J.k; Wagner, J.M. J. Org. Chem.,
60, 2613
1995,
Me
Cl
N=CMe2
,100°C,9h
NH2
t PPTs , NEt3 , sealed tube
PPTs = pyridinium p-toluenesulfonate Morris,;
Wishka, D.G. J. Org. Chem.,
1995,
quant.
60, 2642
OEt
lx NHMe
OSiMej
’ AcoH
*
NaCNBH4, MeOH Gillaspv. M.L.. . Lefker. B.A, ; Hada, W.A.; Hoover, D.J. Tetrahedron Lett.,
\ 1995,
P Me 36,
75%
7399
Compendium
128
Bn I
0.2 MeLi,
SnMe4, THF
-6
SnMe3
N I Bn
eNvSnMe3 Cold-,
Section 97
of Organic Synthetic Methods, Vol9
Hufton, R. Tetrahedron
0
70%
Lett., 1995, 36,2157
1. set -BuLi , TMEDA 2. Phi , [P(o-Tol)3]4Pd-CuCN
N 75OC , 18h, toluene I Boc Dieter, RK,; Li, S. Tetrahedron Lett., 1995, 36, 3613
t
CL
Jl?
Br L
N
C02Me
N In,THF,
54% Ph
N I Boc
15h
v CO2Me 50% Bossard, F.; Dambrin, V.; Lintanf, V.; Beuchet, P.; Mosset. P, Tetrahedron L&t., 1995, 36, 6055 @,,(
Me
Me0
Bu = 5=
\ BuLi , ether, 0°C
*
Ph;
LiBr ,5h
Hashimoto.
Y,; Kobayashi, N.; Kai, A.; Saigo, K. SynZett, 1995,
Me N I H
80% (98:2 anti:syn) 961
‘-Ar Bu$nH
, AIBN,
PhH ,80°
Ar = 4-chlorophenyl Gioanola, M.; Leardini. R.; Nanni, D.; Pareschi, P.; Zanardi, G. Tetrahedron,
71% 1995, 51, 2039
Section 99
Amines from Ethers
129
1. (HCHO), , &Cl;!
BnzNH
* 2.ZnC12, NaBH4, CHg12, rt Synth. Commun., 1995, 25, 2061
Bhattacharvyu
NH2
dph
90%
B n2NMe
, HCHO 90%
MeCN , TFA, reflux
bklkx
J.M,; Merriman, Ph N
f-
G.D. Tetrahedron, Ph
Ph
1995, 51, 6115
1. &CO3 , KOH , BnBr , CH2Cl2
Ph
chiral ammonium ligand -aH2N 2. H30+ Eddine. J.J,; Cherqaoui, M. Tetrahedron Asymmetry, 1995, 6, 1225
Ph 70% (91% ee)
WdW2 9dppb Ph-NRH t I I I 20°C, 25h he Me quant. Lemaire-Audoire, S.; Savignac, M.; Dupuis, C.; Genet, J.-P. Bull. Sot. Chim. Fr., 1995, 132, 1157 Ph-NW
SECTION
98: AMINES
FROM mt2
ESTERS
9Ni(dppeh t TJJF
* /mNEt2 no yield 80°C B&out, H.; Carpentier, J.-F.; Mortreux. 4 J. Chem. Sot. Chem. Commun., 1995, 1863 moAAc
SECTION
99:
aoMe
AMINES FROM THIOETHERS [ CN-H
ETHERS,
EPOXIDES
AND
/ BuLi] t
/
OMe
TH.F , reflux , overnight
ten Hoeve, W.; Kruse, C.G.; Luteyn, J.M.; Thiecke, J.R.G.; ten Hoeve, W.; Kruse, C.G.; Luteyn, J.M.; Thiecke, J.R.G.; Wynberg, H. J. 0~. Chem., 1993, 58, 5101
130
Section 100
Compendium of Organic Synthetic Methods, Vol9
SECTION
100: AMINES
FROM
HALIDES
AND SULFONATES
Br SmI2, THF , HMPA -42OC
Ph2N-
*Lpt
(-J:y ..
(7 H Sturino, C.F.; Fallis, A.G, J. Am. Chem. Sot., 1994, 116, 7447
\ Q r
n-NEt2,
MeNHBn
5% PdC12(Po-To13)2
1
NMeBn I
toluene, 105OC,4h I 2. HCl / Me 3. MeOH Guram, A.S.; Buchwald. S.L, J. Am. Chem. Sot., 1994, 116, 7901
ph--7 Br
iAmON0,
Bu&,
1) 88%
79% Me
hv (UV lamp)
4h Fletcher, R.J.; Kiril, M.; Murphy. u Tetrahedron
-
‘-N_OH
84%
Lett., 1995, 36, 323
P((o-Tol)3 , LiNTMS2,2h B”-{=)-Br
piperidine , 100°C
* B”-~=~-N(TMs)2 84%
Louie, J.; Hartwig, J.F, Tetrahedron
c3H7v OMs
Lett., 1995, 36, 3689
BuNH2, DMSO , 80°C
2h
*
c3Hv
46%
NHBu Henin. F,; Mahuet, E.; Muller, C.; Muzart, J. Synth. Commun., 1995, 25, 1331 NHMePh , Pd(dba)2/2 P(o-Tol)3 phW{=jWBr
65OC, toluene
*
ph-i=)-NMeph 88%
Guram, A.S.; Rennels, R.A.; Buchwald. SL Angew. Chem. Int. Ed. En&
1995, 34, 1348
Section 102
SECTION
Amines from Ketones
101: AMINES
FROM
131
HYDRIDES
Me 1.65OC, 24h
b Cl~H2C02CN==N-C02CH2CQ 2. Zn , AcOH Zaltsgendler, I.; &&&,nc. Y,; Bernstein, M.A. Tetrahedron
SECTION
102: AMINES
FROM
H2
Lett., 1993, 34, 2441
KETONES
DMF , NH40Ac 0 Westerwelle,
U.; Risch. NI Tetrahedron
Lett., 1993, 34, 1775
1. LDA , nitroethylene , ZnC12, THF , -3OOC 2. Ni(R) , EtOH , H2 (50 psi) Ph
JL
Ph
3. NaBHcN
, AcOH , EtOH , O°C *
&I. K; Behnke, M.L.; Tong, L. Tetrahedron
P
Ph 2-J
H
77x95x100%
Lett., 1993, 34, 6205
H+ , Si(OEt)d , HflCHPh2 Ph
bve.
BE;
Ren, J. J. Org. Chem., 1993, 58, 5556
72%
Ph
1, lo-phenanthroline , CO Ru3(CO) 12, p-dioxane 91% 140°C, 16h 0 NO2 Watanabe. Y,; Yamamoto, J.; Akazome, M.; Kondo, T.; Mitsudo. T,J. Org. Chem., 1995, 60, 8328 pi
132
Compendium of Organic Synthetic Methods, Vol9
Section 104
Related Methods: Section 94 (Amines from Aldehydes)
4
SECTION
\
103: AMINES
/
m-0 0
FROM
NITRILES
0
PhMgCl , CH2C12 5h, -78OC + rt 96%
Kim, J.N.; Km, H.R.; Byu. E.K, Tetrahedron
Lett., 1993, 34, 5117
QM e t-BuCN ,t-BuOMe O°C (lh) , reflux (2d) w
c. C.pL; Bums, E.E. Tetrahedron
Lett., 1993, 34, 5401
BuMgCl , PhH/ether , rt Br”CN
Bu
N
84% Fry. D.F,; Fowler, C.B.; Dieter. R.L Synlett, 1994, 836
Ph-CN
\
2eq.HC=CH,hv,H@,3h
I w$-w-w@od~
1
Heller. B .; Oehme, G. J. Chem. Sot. Chem. Commun.,
SECTION
104: AMINES
FROM
I CL
* 1995,
N
0
41% Ph
179
ALKENES
PhNH2, PhNHLi ,12d [R.hCl(PEt$& , 70°C-
P 4
N-Ph
65% (+ 30%N-phenyl phenethylamine and 5% N-phenyl-2-phenylethane) net. J.-J%;Neibecker, D.; Philippot, K. Tetrahedron
Lett., 1993, 34, 3877
Section 105
Amines from Misc.
6P
133
NsONHC02Et, CH2C12 KzC03, lh , rt 62%
** / EtOg Fioravanti, S.; Loreto, M.A.; Pellacani, L.; Tardella, P.A. Tetrahedron
Lett., 1993, 34, 4353
1. O3 , CH2C12, -78OC * phw
2 . 2eq .
N-H
phw
c 4A MS , CHg12, reflux Hon. Y.-S.; Lu, L. Tetrahedron Lett., 1993, 34, 5309
85%
NHPh PhNHOH , Fe(Pc)
76%
Ph A
-LPh PC = phthalocyanine Johannsen, M.; Jtirgensen, K.A, J. Org. Chem., 1994, 59, 214 HZr(CI)Cp2:RONH2 * THF
Bum
BumNH2
77%
R = Me$J&OS02Zheng, B.; Srebnik. M, J. Org. Chem., 1995, 60, 1912
SECTION
105:
AMINES
FROM
+ 22% PhNH2
MISCELLANEOUS
COMPOUNDS
1. BuLi , BFseOEt2, toluene 2, LiAIH4
\ r. R&;
70% (60% de)
Datar, R. Can. J. Chem., 1993, 71, 814
R Ph+Ph Ph Coumbe, T.; m.
(EtO)$iH
, Ti(OiPr)d * 67OC
N.J.; Muhammad, F. Tetrahedron
PlY
P Ph
Ph
L&t., 1994, 35, 625
85%
134
Compendium of Organic Synthetic Methods, Vol9
Section 105
/-
C02Me
1. Bu$nH , AIBN MeCN , 100°C
COzMe
Ph
2. PhBr , NEt3, 100°C 5% Pd(PPh3)4 Fukuyama. T,; Chen, X.; Peng, G. J. Am. Chem. Sot., 1994, 116, 3127
\‘\ /\ I b
r
Bn
toluene ,75OC 14h
+
OMe
I
Bn
N=PPh3
OBn Me0
OBn Ar = 3,4-dimethoxyphenyl
Me0 Rodriaues. J.A.R,; Leiva, G.C.; de Sousa, J.D.F. Tetrahedron L&t., 1995, 36,59 Ph’-N/OBn
+
(BnNEt&MoSd , MeCN , rt
I
*
\ 76%
Ph-NNBn
Ar
86%
00
Ilankumaran, P.; mkaran.
S, Tetrahedron L&t., 1995, 36,488l
1. Hg(OAc)z , aq. THF t cti 2. NaBH4, OHMalanrza, C,; Urso, A.; Lardicci, L. Tetrahedron Lett., 1995, 36, 8859
quant.
17CH2NH2
Et3SiH , Ni(OAc)ze4 Hz0 -
PhvN-ph
PhdNHPh
NH2
95% Vetter, A.H.; Berkessel. A, Synthesis, 1995, 419
10% Yb(OTf)3, MeCN OMe
Makioka, Y.; Shindo, T.; Taniguchi, Y .; Takaki. K,; Fujiwara, Y. Synthesis, 1995, 801
Amines from Azides
Section 105
PhCH=N-OH
135
BER-Ni(OAc)z , MeOH, 75OC w
81%
PhCH2NH2
BER = borohydride exchange resin B.P,; Nikat, S.M.; Wadgaonkar, P.P. Synth. Commun., 1995, 25, 863
Ban&~.
1. A@
C6H13
N-OH F
Me
2. NaBH4,12
arbrv. DJ Champagne, P. Synth. Commun., 1995, 25, 3503
u
Ph
Cp2MoH2, toluene
-N’ 89%
Minato, M.; Fujiwara, Y.; Ito. T. Chem. Lett., 1995, 647 Ph
Ph
BnNH2, Hz, Ir(R-BINAP)
N-Bn
N-Bn MeOH
quant. (66% ee , S) Onouchi, J.; Yamagata, T.; Kataoka, Y. Chem. Lett., 1995,955
Tani.;
AMINES BUiN3
FROM
BER-Ni(OAQ2,
AZIDES MeOH
fjuBNH2 w
rt, 30min m.
96%
BER = borohydride exchange resin N.M.; Choi, J.; Shon, Y.S. Synth. Commun., 1993, 23, 3047 NaBHa, cat. CuSO4, MeOH BUN3
*
95%
BuNH2
Rao, H.S.P,; Siva, P. Synth. Commun., 1994, 24, 549
Ni
H2N
96% Benati. L,; Montevecchi, PC.; Nanni, D.; Spagnolo, P.; Volta, M. Tetrahedron 7313
Lett., 1995, 36,
136
Compendium of Organic Synthetic Methods, Vol9
Section 105
LiMezNBHg , THF , O°C N3
NH2
1995,
-
-
w11-
Alvarez, S.G.; Fisher, G.B.; Singpam. B, Tetrahedron Lett., 2SSmI2,THF,rt,
lh
Clti21-N3
Goulaouic-Dubois, C.; J-Iesse. M, Tetrahedron Lett.,
1995,
90%
36, 2567
85%
Clti2l---NH2
36, 7427
BHC12*SMe2 ) CH2C12 Wl(\N3
Salunkhe, A.M.; Brow-
Tetrahedron
AMINES
FROM
NH2
95%
L&t., 1995, 36,7987
NITRO
COMPOIJNDS
1.7 eq. SmI2, THF/MeOH rt, Id 2. oxalic acid/water
ess. M.&
Yarberry, D.J. Tetrahedron Lett., 1993, 34, 4743
Mahdavi, F.; Bruton, T.C.; Li, Y,J. Org. Chem., 1993, 58, 744 borohydride exchange resin NO2
Yoon. N.&;
Ni(OAc);!, MeOH , rt ,30 min
Choi, J. Synlett, 1993, 135 NO2
b \
I
/
Baker’s yeast, NaOH aq. MeOH, 80°C, 4h
Br Br Baik, W.; Han, J.L.; Lee, KC.; Lee, N.H.; Kim, B.H.; Hahn, J.-T. Tetrahedron Lett., 1994, 35, 3965
Section 105A
protection of Amines
137
1. CuBraSMe;! , NaBH4 , THF
PhNO2
w 2. MeOH , 10°C Patel. HV,; Vyas, K.A. Org. Prep. Proceed. Int., 1995, 27, 81 HZN-NMe2 , FeC13 , MeOH,
PhNH;!
81%
18h
NO2
Boothroud,
89%
NH2
S .R.; Kerr, hzB, Tetrahedron
Lett., 1995,
36,
2411
NaBHq-BiCl@tOH ,2h b 86% PhNO2 PhNH2 Ren, P.-D.; Pan, S.-F.; Dong, T.-W.; Wu. S.H,Synth. Commun., 1995, 25, 3799
90% Gohain, S.; Prajapati, D.; mu.
J& Chem. Left., 1995, 725
REVIEWS: “Asymmetric Reductions of C-N Double Bonds. A Review,” Zhu, Q.-C.; &tchins. R.0, Org. Prep. Proceed. Int., 1994, 26, 193 “Reduction of Nitro-Substituted Tertiary Alkanes,” Weis, C.D.; Newkome. G.R, Synthesis, 1995, 1053
SECTION
105A: PROTECTION
OF AMINES
KF , NEt3 , DMF P BoqO
Li, W-R.; Jiang, J.; Joullie, M.M. Tetrahedron
a
pfi r H
e
, rt , 10h
Lett., 1993, 34, 1413
Pd(;qALC;;Iift2NH . 9 t
+
PPNH2
72% also with carbonates to give alcohols Genet. J.P.; Blart, E.; Savignac, M.; Lemeune, S.; Paris, J.-M. Tetrahedron L&t., 1993, 34, 4189
138
Compendium of Organic Synthetic Methods, Vo19
Section 105A
1. TMSI , HMDS , MeCN +H 3 2. DABCO 3. HCl , Hz0 0
Cl
Cl
0
++
70% c02C02H Fisher. J.W,; Dunigan, J.M.; Hatfield, L.D.; Hoying, R-C.; Ray, J.E.; Thomas, K.L. Tetrahedron m
Lett., 1993, 34, 4755
Pd(PPh3)4, NDMBA , 30°C CH2C12, 1Sh
Ph-NW
*
Ph-NH
LY NDMBA = N,N-dimethylbarbituric acid Garro-Helion, F.; Merzouk, A.; Guibe, F. J. Org. Chem., 1993, 58, 6109 Meo~gC02t-Bu NHBoc
BnzN-SOzPh
quant
1M HCl , EtOAc Meog$cIFu w rt ,5h
Gibson, F.S.; Bergmeier, S.C.; Panoport, H, J. Org. Chem., SmI2, THF , DMPU , reflux
1994,
b
quant. 59, 3216
Bnfl-H
Pd(dba)z, dppb , 20°C ,25 min t
I Me
I Me quant.
2-(SH)C6H4COOH, THF
Lett., 1995, 36,
CF3C02Et, THF ) O°C c
selective for lo amines Xu, D.; prasad. K; Repic, 0.; Blacklock, T.J. Tetrahedron Lett.,
-
Ph-NOH
Lemaire-Audoire, S.; Savignac, M.; f3;rznZt.J.P,; Bernard, J.-M. Tetrahedron 1267
MeHNwNH2
3+
92%
4.5h Vedejs, E,; Lin, S. J. Org. Chem., 1994, 59, 1602 Ph-NW
2
MeHNwNHTFA 1995,
>95% 36, 7357
Section 105A
CL
Protection of Amines
139
, DCE , reflux
N Me 2. MeOH, reflux I Bn Yane. B.V,; O’Rourke, D.; Li, J. Synlett, 1993, 195
*
TiC13-Li , THF , reflux ,22h Me2NBn c, Talukdar, S.; Banerji. A, Synth. Commun., 1995, 25, 813
(R
74% N I H
Me2NH
Me
55%
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
140
Section 107
Compendium of Organic Synthetic Methods, Vol9
CHAPTER
8
PREPARATION
3
SECTION
OF ESTERS
106: ESTERS FROM ALKYNES OH
xylenes , 150°C
H OEt
~ 72%
OH Liang, L.; Ramaseshan, M.; MaGee. D.1, Tetrahedron,
SECTION
0
0
1993, 49, 2159
107: ESTERS FROM ACID DERIVATIVES
The following 1. 2. 3.
2x
types of reactions are found in this section:
Esters from the reaction of alcohols with carboxylic acids, acid halides and anhydrides. Lactones from hydroxy acids Esters from carboxylic acids and halides, sulfoxides and miscellaneous compounds 0 0
tiI
0 Li [Binol-AlHOEt] -78OC +
, THF rt -
0 Matsukl.;.
(84% e-e)
Inoue, H.; Takeda, M. Tetrahedron CO2I-r
0
I ti
Lett., 1993, 34, 1167
PhCHzOH ,2,6-lutidine C
k/ Cl 00S\fN
Cl
\
Folmer, J.J.; Weinreb. SM, Tetrahedron
9 C&C12
-78OC + rt Lett., 1993, 34, 2737
C02CH2Ph
81%
69%
Section
Esters from Acids
107
K
141
2
H
Si( iPr),
a
90°C
OH Soderauist, J.pL; Miranda, E.I. Tetrahedron Lett., /
0-S 1993,34,4905
/
C02H
TEOA = triethyl orthoacetate Trujillo, J.I.; Goaalan.AS, Tetrahedron Lett., 1993,
i(iPr)3
93%
C02Et
7355
34,
C&Il@H , TsOH, neat PhC02H
my.
PhC02C8H17 97% microwave,3 min A,; Petit, A.; Ramdani,M.; Yvanaeff,C.; Majoub,M.; Labiad,B.; Villemin. D, Can. J.
Chem., 1993, 71, 90
Ph-CO
1. NBS CH$I;!, MS 481 O°C, PPh3
2H
2. PhCH20H, Py , lh Sucheta,K.; Reddy,G.S.R.;Ravi, D.; -Q&W.
fd
Ph
phwco2H
~
VPh
Ph 7
x Tetrahedron
98%
0 Lett., 1994, 35, 4415
20%Tic14+ 2 AgC104 Ph+P (ArCO)20 9MS3A Ar = 3,5-trifluoromethylphenyl Shiina,I.; Miyoshi, So.; Miyashita, M.; Mukaiyama,T. Chem. Lett.,
HOqCHz)lo
JL OH
Ph
0 OH
5%TiCLz(OTf)z, (ArCO)20 3 TMSCl , CH2C12 (2 mM) reflux (slowadditionover 5 h)
Ar = 4-trifluoromethylphenyl Shiina, I.; Mukaiyama,T. Chem. Lett., 1994, 677
*
0
90% 1994,
515
A==
0
CJ32ho
83% + 10%diolide
142
Compendium of Organic Synthetic Methods, Vol9
C17H31C~H
*
cat. DMAP , lh
Section 108
C1f131C%cH~H=CH2
85% Akiyama, A.; Konda,Y.; Takayanagi,H.; Harigaya,Y. Tetrahedron Mt., 199% 36,
NK.; 113
Togo. H,; Muraki, T.; Yokovama.M, Tetrahedron
Lett., 1995, 36, 7089
Bu-C=C-H, 100°C,5 eq.NEt3 5% Pd(PPh&t, ZnCl;! 84% Liao, H.-Y.; Chew. E.H, J. Org. Chem., 1995, 60, 3711 Furtherexamplesof thereactionRC02H + R’OH + RC02R’areincludedin Section108(Estersfrom AlcoholsandPhenols)andin Section30A (Protection of CarboxylicAcids).
SECTION
108: ESTERS
FROM
ALCOHOLS
AND THIOLS
Furtherexamplesof thereactionROH + RCO2R’areincludedin Section107 (Estersfrom Acid Derivatives)andin Section45A (Protectionof Alcoholsand Phenols). 1. BuLi, THF, rt PhmOH
;s ph/n/Yco2Et . C02Et 5% Pd(PPh3)4,8h (80:20 E.-Z) 10%PPh3,reflux Star$, I,; Star& I.G.; IWovsky, P. Tetrahedron Lett., 1993, 34, 179
80%
Section 108
143
Esters from Alcohols
OH
&&j)oa.
CL;
3.5 Ca(OC1)2,2
C02Me
AcOH
89%
32MeOH,darkJd MeCN , rt Nice, L.E.; Shaw, A.W.; Nestor, N.B. Tetrahedron
Lett., 1993, 34, 2741
1. sOC12, DMF
4 C 13H27CH20CH0 2. H20 I.; Garcia, B.; MuAoz, S.; Pedro. J.R,; de la Salud, R. Synlett, 1993, 489
CL3H2$H20H Femtidez, tioH
KNOflFyl.25
Hz0
CH2C12,O”C
+ rt
-
95%
-ON02 95%
Olah. G.A,; Wang, Q.; Li, X.; P&ash,
G.K.S. Synthesis, 1993, 207
1. Cr(CO)9THF,
THF, 55OC t
w. 81%
m.
P,; Rahman, S.; Ward, E.L.M. Tetrahedron
Lett., 1994, 35, 3801
Pb(OAc), , PhH , CO C3H77
OH
Tsunoi, S .; Byu. I.: Son& Hok
m
40°C) Id
N, .I. Am. Chem. Sot., 1994, 116, 5473 NaBrO2, Al203 9 c&cl2
57%
.
T,; Hirano, M.; Iwasaki, K.; Ishikawa, T. Chem. Z&t., 1994, 53
MeC(OEt)3
, EtC02H,
microwave , 12 min
A,; Nagaraju, S.; Kondaiah, P. Tetrahedron,
DMF
c
1995, 5I, 1809
63% C02Et
144
Compendium of Organic Synthetic Methods, Vol9
Section 109
OH
02cAr TMAD , DEAD, Bu3P, PhH 4-(MeO)C6H4COOH, 60°C, Id
“W,,,, * b TMAD = Me2NCON=NCONMe2 A Mitsunobu reaction for sterically hindered alcohols 98% Tsudoda. T,; Yamamiya, Y.; Kawamura, Y.; Ito, S. Tetrahedron Lett., 1995, 36, 2529
C
OH
3 eq. NCS , CH2C12, 20°C, 5h
OH
-do.
S,; Kawasoe, S.; Kunisada, H.; Yuki, Y, Synth. Commun., 1995, 25, 719 NaBrO3,
NaHS03,
88%
II20
C3H7-OH rt ,2h
0-w
76% Takase, K.; Masuda, H.; Kai, 0.; Nishiyama, Y.; Sakaguchi, S.; Ishii. Y, Chem. Lett., 1995, 871
SECTION
109: ESTERS FROM ALDEHYDES
Bu-CHO
. Lmdennan.
1. Bu$nLi 2. MOMCl
0
, iPr$Wt
3. O3 , CH2C12, -78OC (quoter R&; Jaber, M. Tetrahedron Len., 1994, 35, 5993
o-o’
OCHO 94%
mcpba , CH2CI2, rt ,2Sh *
‘OMe e. B,; Aly, M.F.; Sierra, M.A. Tetrahedron
-0Me L&t., 1995, 36, 3401
Section 111
Esters from Amides
145
CHO 1% CU(OAC)~~~ H20, 02, DCE
c
3 iPrCH0
87%
OMe
OMe
Anoune, N.; Lam&i, P.; Longeray, R.; Amaud, C. Tetrahedron
PhCHO
PhI(OAc)2, NaN3, PhSSPh
Lett., 1995, 36, 6679 0
/
CH2C12,rt Tinnoli. MJ Temperini,A.; Testaferri,L.; Tiecco,M. Synlett,
PhCHO
A@, HY zeolite, CC14
1995,
62%
SPh 1129 OAc
=
Ph --<
98% OAc Pereira,C.; Gipante.BJ Marcelo-Curto,M.J.; Carreyre,H.; Perot,G.; Guisnet,M. Synthesis, 1995,1077
RelatedMethods:Section117(Estersfrom Ketones)
SECTION
110:
ESTERS FROM AND ARYLS
ALKYLS,
METHYLENES
No examplesof thereactionR-R + RC02R’or R’C02R(RR’ = alkyl, aryl, etc.) occurin the literature. For the reactionR-H + RC02R’or R’C02R,seeSection 116(EstersfromHydrides). NO ADDITIONAL EXAMPLES
SECTION
111: ESTERS
FROM
AMIDES
0
7-lK
N\
3
S
1. LiAlH4, O°C 95% 2. TsOH, H20, CHg12 *
S
0
90%
25OC
4 CananKoch, S.S.;Chamberlin.A.R, J. Org. Chem.,
1993,
58,
2725
146
Compendium of Organic Synthetic Methods, Vol9
Section 113
TiC14, MeOH ,3h Ph
Ph NHOMe
OMe
86% Fisher. L.E,; Caroon, J.M.; Stabler, S.R.; Lundberg, S.; Zaidi, S.; Sorensen, C.M.; Sparacino, M.L.; Muchowski, J.M. Can. J. Chem., 1994, 72, 142
1. BDMAB 2. NaBH4
Kanti;
, Zn complex , -1OOC
69% (84% ee , lR2S) Lett., 1995, 36, 4265
Lee, J.W.; K im, J.I.; Pyun, C. Tetrahedron
SECTION
112: ESTERS
FROM
AMINES
NO ADDITIONAL
SECTION
113: ESTERS
FROM
EXAMPLES
ESTERS
Conjugate reductions and conjugate alkylations of unsaturated esters are found in Section 74 (Alkyls from Alkenes). 1. N2CHC02Et,
CH2C12
RbpAd4
* 2. iPrOH , NEt3 Andrey, 0.; Landais. Y,; Panchenault, D. Tetrahedron Me2SiClH
0
(iPrO)Me2SiCH2CO$t Lett., 1993, 34, 2927
10% TiC14,2 AgC104, CH2C12 =, OSiMe3
Mukaiyama,
74%
@r-CO&O
, rt , 3 hr addition
0
A== CH2ho
Ar - 4-trifluoromethylphenyl T.; Izumi, J.; Miyashita, M.; Shiina, I. Chem. Lett., 1993, 907
75%
1. LDA , Me3siCl Ph OMe . ng&. S.W. Tetrahedron
2. H2Se Lett., 1994, 35, 1331
OMe
74%
Section 113
147
Esters from Esters
PH
0.1 eq. Bu3SnOMe , decalin , heat OCH2CF3
81% + 14% diolide
0 [ with BuSnH/AIBN + 70% lactone + 0% diolide ] White. J.D; Green, NJ.; Fleming, F.F. Tetrahedron Let&, 1993, 34, 3515 2.5% [Pd(n3-C3H$C1]2 C&C12 ,36h , CH2(COzMe)2 Ph
BSA,AcOK,rt
6% 3@-** T 84% (89% ee,S)
BSA = N,O-his-(trimethylsilyl)acetamide Kubota, H.; Nakajima, M.; Kona. K, Tetrahedron
Lat., 1993, 34, 8135
/‘COzEt TMSCl , NaI , MeCN t
J?iva. 0, Tetrahedron,
82%
1994, 50, 13687 0
hv , NaBH3CN , MeOH wwho,
0 *
0
3h, rt
d (CH2ho
83~74% Abe, M.; Hayashikoshi,
T.; Kurata. T, Chem, Lett., 1994, 1789
0 46% (4060 cixtrans) Muller.
P,; Polleux, P. HeZv. Chim. Acta, 1994, 77, 645
148
Section 114
Compendium of Organic Synthetic Methods, Vol9
o-
,#4@
0
l.LDA,THF 2. BnBr , THF , -78OC 0
3. satd. NH&l,
-78OC
83% (1O:l antixyn) Anceau,C.; Dauphin,G.; Coudert,G.; Guillaumet.G, Bull. Sot. Chim. Fr., 1994, 131, 291
Ph
3 BuCHO,3 Mg ,3 TMSCl Ph-co*Et
DMF
74% Ohno, T.; Ishino,Y.; Tsumagari,Y.; Nishiguchi.IJ. Org. Chem., 1995, 60, 458
-d BnOg
chiralTi complex,I2 , CuO /=>H2q02Bn C02Bn
CH2C12,13h
0
cQ H 1@ quant (76%ee)
Inoue,T.; Kitagawa,0.; Kurumizawa,S.; Ochiai,0.; Taguchi.T, Tetrahedron L&t., 1995, 36, 1479
2 eq.In , DMF )(
+
. Schick.;
SECTION
jl,,. 62%
Ludwig, R.; Kleiner,K.; Kunath,A. Tetrahedron,
114:
ESTERS FROM THIOETHERS
ETHERS,
1995,
51, 2939
EPOXIDES
AND
1.5AcBr ,5% SnBr2 .
WT.;
Pd\/Oms Oda, M.; Gono, J.; Koga,G. Tetrahedron
*
Pd\/O””
Lett., 1994, 35, 2027
9%
Section 115
149
Esters from Halides
0
0 Sasidharan, M.; Suresh, S.; Sudalai.
Tetrahedron
55%
t
TS-1, H202 TS-1 = titanium silicate
(x.
SnBrrAcBr , CH2C12
PhCH2CH20CH2Ph
0
0
36, 9071
Lett., 1995,
e
rt, lh
PhCH2CH20Ac 92%
Orivama. TJ Kimura,M.; Oda, M.; Koga,G. Synlett,
437
1993,
NdBq , AcOH , microwave 1.7min Yulin, J.; Yuncheng, Y. Synth. Commun., 1994,
24,
82% 1045
PdClz-CuC12 ,@ , acetone + CO (60 atm),2d Miyamoto,
M.; Minami,
Y.; ui.
67 atmCO, 180°C,PhH ,2d o-
OEt
S
)
Chem. Lett., 1994,
lm~cod)c~l2
115: ESTERS
FROM
HALIDES
1149 73%
()C02Et
S
Khumtaveepom,K.; A,@g. & J. Chem. Sot. Chem. Commun.,
SECTION
16% ’
Y,; Kinoshita, H.; Inomata.
1995,
917
AND SULFONATES
1. (MeS)cLi , THF , -78OC *
BuBr Barkro,
91x84%
BuCOSMe
2.35% aq. HBF4, THF , 70°C M.; Cadamuro, S.; Denani. I,; Dughera, S.; Fochi. R, J. Chem. Sot., Perkin Trans. I.,
1993,2075
Y
Ph &tt. L Tetrahedron
ph/\/OTS
Cl
BrZnCH2CO$t C02Et CH2C12,0°C + 20°C
Lett., 1994,
69%
35, 555
cat. Bt4NN03, NaNO3,PhHIH20 ) sealedtube(135°C)
Hwu, J.R,; Yyas, K.A.; Patel, H.V.; Lin, C.-H.; Yang. J&Synthesis,
ph/\/oNo2 81% 1994,
471
150
Compendium of Organic Synthetic Methods, Vol9
Section 116
Br A.rOK , CO, PdC12(dppp), PhH * loo”c Ar = 2,5-di-t-butyl-4-methylphenyl
Ph
Ph Kubota, Y .; Hanaoka, T.-a.; Takeuchi, K.; Sugi. Y cJ. Chem. Sot. Chem. Commun., 1994, 1553
OMs
PhCH2H,CsF, DMF , 60°C *
OBz Z Z
17h
Me
50% (100%ee)
Sato, T.; Otera. J, Synlett, 1995, 336 RelatedMethods:Section25 (Acid Derivativesfrom Halides). SECTION
116: ESTERS FROM HYDRIDES
Thissectioncontainsexamplesof the reactionR-H + RC02R’or R’C02R (R = alkyl, aryl, etc.).
0 /
10%5% 0 Pd(OAc)z 0 , 1.5 ’ AcOH Hz02
# m.M;
OAc
2h, 50°C
Oslob,J.D. J. Org. Chem., 1994, 59, 5729 PhCO#-Bu,5% CuOTf ,23OC MeCN ,4d w
8%
0 3% 4
N
0 N 39
r
%
Gokhale,A.S.; Minidis, A.B.E.; Pfaltz. A, Tetrahedron
Let?., 1995, 36, 1831
Section 117
Esters from Ketones
0
151
+ o=
RuC13.n Hz0 , rt OzCCF3
2 eq. MeC03H TFA:CHglz
Murahashi.
69% S,; Oda, Y.; Komiya, N.; Naota, T. Tetrahedron
12% Lett., 1994, 35, 7953
5% chiral bis-oxazoline Cu complex PhCOzt-Bu , MeCN , -2OOC
-0
Andrus.;
,\,,w OB z
Argade, A.B.; Chen, X.; Pamment, M.G. Tetrahedron Cu(OTf)z(chiral
0
49 % (81% ee) Lett., 1995, 36, 2945
amine)3 , PhCO$-Bu
OBz
rt ,4Oh Kawasaki,
K.; Tsumura, S.; Katsuki. TJynZett, 2 eq. PhCO+Bu
0
1995, 1245
,3 eq. PhC03H OBz
PhH ,4h, 0.1 Cu20, reflux , air 59% (45% ee , S)
Levina, A.; Muzart, J, Tetrahedron
Asymmetry, 1995,
6, 147 0
0
Cu(OAc)z , S-proline , EtC@H PhC03t-Bu ,
0 II/
20°C, 16h
70% (57% ee) R&ens, M.T.; Zondervan, C.; Rispens, M.T.; Zondervan, C.; Feringa, B.L. Tetrahedron Asymmetry, 1995, 6, 661 Also via: Section 26 (Acid Derivatives) and Section 41 (Alcohols).
SECTION
117: ESTERS FROM KETONES 02 (1 atm), 3 eq. PhCHO, 21h 0.2 CU(OAC)~~H~O , DCE dark
l&Q&
C,; Schlingloff,
G.; Weickhardt,
K. Tetrahedron
94% -x3 Lett., 1993, 34, 3405
152
Compendium of Organic Synthetic Methods, Vo19
THF* ,25OC
Section 117
CO2Me + 72%
C1/\/Co2Et , DM’F o=
Fermin,M.C.; Bruno. LW%Tetrahedron Lett., 1993, 34, 7545
0
e’ , SmC13 , Mg anode
60% Hebri, H.; Duiiach,E.; Perichon,J. J. Chem. Sot. Chem. Commun., 1993,499 0
MeOC02Me, 195OC,K2C03
Ph A
0 *
Ph A
6.4h
OMe 71%
Selva, M.; Marques,C.A.; Tundo. P, Gazz. Chim. Ital., 1993, 123, 5 15
o= 0
3 PhCHO, Ccl4 02,4O”C
Kaneda., Ueno,S.; Imanaka,T.; Shimotsuma, E.; Nishiyama,Y.; Ishii, Y. J. Org. Chem., 1994, 59, 2915
0
NBS, DME&O O°C,30 min
0 82%
Marotta, E.; Piombi,B.; Righi, P.; hsini. G, J. Org. Chem., 1994, 59, 7526 0
PhCHO,5% MnO2 DCE,02,rt,ld
of
Inokuchi, T.; Kanazaki,M.; Sugimoto,T.; ~Torii.
t co
68% Synlett, 1994, 1037
Section 118
Esters from Nitriles
Q= 0
PhCHO 9 02, Mgm&(OH)2&03
DCE , 40°C, 5h
153
-o= 0
0
90%
Kaneda.K,; Ueno, S.; Imanaka,T. J. Chem. Sot. Chem. Commun., 1994, 797
48%
Chida,N.; Tobe,T.; Ogawa,S. Tetrahedron LRtt., 1994, 35, 7249 0
Ph 02, t-BuCHO, Cu complex 41%(65%ee) Ph Balm. (1,; Schlingloff, G.; Weickhardt,K. Angew. Chem. Int. Ed. Engl., 1994, 33, 1848 0
02 , 1%Cu complex a t-BuCHO H
0
+ H
H
1 [92%eel) 61% (3 [67%ee] : Balm. CJ Schlingloff, G. J. Chem. Sot. Chem. Commun., 1995, 1247 Also via: Section27 (Acid Derivatives).
SECTION
118: ESTERS
FROM
NITRILES
cat. RuH2(PPh3)4, H20 W-J
1lCN
*
C5H1A02
72% Naota,T.; Shichijo,Y.; Murahashi.S.-I, J. Chem. Sot. Chem. Commun., 1994, 1359
154
Compendium of Organic Synthetic Methods, Vol9
SECTION
119: ESTERS
FROM
Me
ALKENES Me
P
03 , -78°C) MeOH/CH$12 * 5 eq. NaOH
/
K/
Section 120
C~HI~~CO Marshall. J.A.; Garofalo, A.W. J. Org. Chem., 1993,58, 3675 C6Hl
CH2(C02Me)2,Mn(OAch
*
ultrasound Allegret& M.; D’Annibale,A.; Trogolo, C. Tetrahedron,
2Me
C02Me I
2
0
0 1993, 49, 10705
78%
V205, TFA , 70°C, 5h
w-d-@
w
Choudarv.B.M,; Reddy,P.N. J. Chem. Sot. Chem. Commun., 1993,405 0
ICH2C02Et,Cu , 130°C
70%
Metzger. J.a; Mahler, R. Angew. Chem. Int. Ed. En@., 1995, 34, 902 Also via: Section44 (Alcohols).
SECTION
120:
ESTERS FROM COMPOUNDS
MISCELLANEOUS
1. BuLi 2. CNC02Me 44% 3. TBAF, THF 65% SO2Ph 4, Al/Hg , aq.THF 60% Robin,S.; Huet. F, Tetrahedron
Lett., 1993, 34, 2945
63%
-c!!l
\\# +$(r\
Section 120
Esters from Misc.
Et-O,
155
CO, EtOH , iE’@Et 2% Pd(PPh3)4, 50°C
/OEt
*
Il’OEt 0 also works with allylic acetates Murahashi. S-1,; In&a, Y.; Taniguchi,
Et-C02Et
30 atm (E.-Z 84:16) Y.; Higashiura,
88%
S. .I. Org. Chem.,1993,
58, 1538
1. SmI2, HMPA , THF , t-BuOH reflux , lh 2. H2ClO4 99% Fukuzawa.
S,; Tsuchimoto,
T. Synlett, 1993, 803
. Phy
TO,,,: bSiMe3
Miyashita,
M.; Shiina.; F
Ph-
90%
20% Tic14 + 2 AgC104 bAc CH2C12, r-t, 3h Miyoshi, S.; Mukaama. T, Bull. Chem. Sot. Jpn., 1993, 66, 1516
OMe
N,-/ a3 \-/ Lai. L.-L;
(PhC0)20
n
Me$iSNz
, 120°C
w
DMEU ,18h
DMEU = 1,3-dimethyl-2-imidazolidinone 63% Lin, R.Y.; Huang, W.-H.; Shiao, M.-J. Tetrahedron Letk, 1994, 35, 3545
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
156
Section 123
Compendium of Organic Synthetic Methods, Vol. 9
CHAPTER
9
PREPARATION OF ETHERS, AND THIOETHERS
SECTION
121:
ETHERS, EPOXIDES FROM ALKYNES
EPOXIDES
AND THIOETHERS
1. Me$vBu MeCN , rt 2. NaOPh , MeOH ura. T,; Zheng, L.; Taniguchi,
H.; Sakurai, M.; Tanaka, R. Tetrahedron
Lett., 1993, 34,
4055
SECTION
122:
ETHERS, EPOXIDES AND THIOETHERS FROM ACID DERIVATIVES NO ADDITIONAL
SECTION
EXAMPLES
ETHERS, EPOXIDES AND THIOETHERS FROM ALCOHOLS AND THIOLS
123:
NH-@@ Te(iBu)2
OH
Br
NaOH,THF,rt,5h 85% XU,
C.; Lu, S.; Huane. XSynth. H
?
Commun., 1993, 23, 2527
1. Me3SiSSiMe3 2. BF3*OEt2, CH2C12 3. aq. NaHC03
*
C3H7-SwC3H7
C3H7
m.
S.-C,; Yep, G.L.; Chen, B.-L.; Lin, L.C.; Hwu, J.R. Tetrahedron,
75% 1993, 49, 8969
Section 123
Ethers from Alcohols
157
0
MeCOSH , hv, lh
.
(2
1)
0. s.v, ; Tolstikova,L.L; Suslova,E.N.; Voronkov, M.G. Titrahedron
57%
Lett., 1993,
34,3889 1. NaCNBH3, Bu$nCl AIBN , EtOH , reflux
H
PA
*
?
2. NaOH, ether
Pd\/L\CC13
67% (96%ee) Corev. E.J; Helal,C.J. Tetrahedron
Lett., 1993, 34, 5227
QJSMe
CO (100bar), MeOH
98%
J&t. L Chem. Ber., 1993, I26, 1955 PhCH2Cl, cetylMe3NBr,5 min 1
PhCH20H
PhCH2OCH2Ph
microwave
85% Yuncheng,Y.; Yulin, J.; Jun,P.; Xiaohui, 2.; Conggui,Y. Gaze. Chim. Ital., 1993, 123, 5 19 1. AlMe , CH212 (67%--
/OH ==
6:i &ti:syn)
2.p-TsOH (>30:1 (2,3-antixyn)
Panek.J.S,; Garbaccio,R.M.; Jain,N.F. Tetrahedron
BuOH ,0.2 M CAN reflux ,75 min
-
t
Lett., 1994, 35, 6453
OH Iranpoor.N,; Mothaghineghad, E. Tetrahedron, 1994, 50, 1859
158
Compendium of Organic Synthetic Methods, Vol. 9
Section 124
OMe
&rk.R.M.;
Gac, T.S.; Roof, M.T.S. Tetrahedron Lett., SPDBTO
\
1994,
35, 8111
SPDBTO 1. Hg(OAc);! , CH2C12 rt , 18h ) Y + +* 2. aq. NaCl 3. Bu$nH, THF
SPDBTO
# n\/O
OH
+ x
\/O
.
1) 93% Garavelas, A.; Mavropoulos, I.; Perlmutter.P.; Westman, G. Tetrnhedron Lett., 1995, 36,463
(7
v
5% Pd(OAc)2, DMSO ,02 23OC, Id OH
H‘*
*
623
Ronn, M.; BackvaIl, J.-E.; Andersson. P.G, Tetrahedron Lett.,
OH
1995,
BnBr , Cs2CO3, MeCN
OH
92%
OBn
80°C Lee. J.C.; Yuk, J.Y.; Cho, S.H. Synth. Commun.,
90%
,+ H 0 36, 7749
25, 1367
1995,
1. A@ 2. (Cp)zTiMez
OiPr 80x80%
3. H2, Pd/C Billington, D.C.; Dorey, G. Synth. Commun., 1995,
SECTION
124: CHO
CsHlJ
ETHERS, EPOXIDES FROM ALDEHYDES
25,
1633
AND THIOETHERS
BuOH , Pd/C , H2 (40 bar), 100°C
also works with ketones Bethmont, V.; Fache, F.; J,eMaire. M, Tetrahedron Lett.,
w
1995,
c8H13 36,4235
,OBu
95%
Section 128
Ethers from Esters
Me&O-
*
PhCHO Et$iH -s.; 4367
159
, TMSOTf
, CHzC12, -3OOC +
O°C
Mori, H.; Kitano, K.; Yamada, H.; Nishizwa.
(t
Ph-Ow
M, Tetrahedron
CH2N2
CHO
A~(OAI-)~ , -78OC , lh
Maruoka, K.; Conception,
Ar = 2,5diphenylphenyl A.B .; Yamamoto. H, Synlett, 1994, 521
ONTs I Ar’sN Me
83%
,NaH,THF
0 H ‘h,, -5OC, Id PhA Baird, C.P.; Taylor. P.C, J. Chem. Sot. Chem. Comnun., 1995, 893 PhCHO
SECTION
125:
126:
ETHERS, EPOXIDES AND THIOETHERS FROM ALKYLS, METHYLENES AND ARYLS
ETHERS, EPOXIDES FROM AMIDES NO ADDITIONAL
SECTION
127:
ETHERS, EPOXIDES FROM AMINES NO ADDITIONAL
SECTION
128:
ETHERS, EPOXIDES FROM ESTERS 1. Dibal , -78OC
Ph’dco2Me
63% (70% ee)
t
NO ADDITIONAL
SECTION
99% L&t., 1994, 35,
2 . TMSOTf
9Py
Kiyooka. S,; Shirouchi, M.; Kaneko, Y. Tetrahedron
EXAMPLES
AND THIOETHERS EXAMPLES
AND THIOETHERS EXAMPLES
AND THIOETHERS OSiMe3 p
Ph T
OMe Lett., 1993, 34, 1491
91%
160
Compendium of Organic Synthetic Methods, Vol. 9
Section 129
1.2SmI2, -3OOC + l-t Ph
2. A@,
J
Mobder.
DMAP , TEA CH2C12
G.A; McKie, J.A. J. Am. Chem. Sot.,
115, 5821
PhSH, Pd2(dba)3 , dppb ) THF, Id
mocqMe
Goux, C.; Lhoste,P.; Sinou.D, Tetrahedron,
SECTION
1993,
ETHERS, ETHERS,
129:
1994,
EPOXIDES EPOXIDES
AND THIOETHERS AND THIOETHERS
OBn
\a /
ow
2. H30+
Ph
44
S \
Ph
0 Satoh.T.: Horiguchi,K. Tetrahedron OMe
Lett., 1995, 36, 4429
1.2.5 t-BuLi , THF -loo”c
t
2. EtCHO Lett., 1995,
-OH
36, 8235
NaBHgN, Bu3SnCl, AIBN 9h
oc
90% 0
* (x
66%
1994,38,2165
1. e’ , Ni (cyclam), DMF , 20°C Mg anode,C fiber cathode
Me,y A
p-Tel.
d?
I
Olivero, S.; CIinet, J.C.; Dufiach,E. Tetrahedron
FROM
OBn
0
Itoh, A.; Hirose,Y.; Kashiwagi,H.; &&&i. Y, Heterocycles,
I
83%
50, 10321
2 BF3*OEt2,CH2C12 / 0ch
mSPh
12H25
Srikrishna.A,; Viswajanani,R. Synlett, 1995, 95
(t
80%
W2H25
62%
Ethers from Ketones
Section 132
161
Phi ,2% Pd(OAc), ,3 NEt3 6% PPh:, , DMF , 70°C
Hillers, S.; J&ger. 0, Synlett, 1995, 153
SECTION
130:
ETHERS, EPOXIDES AND THIOETHERS FROM HALIDES AND SULFONATES
BER-PhSSPh , MeOH, reflux * CsI-I17-S-Ph Yoon. N.M.; Choi, J.; Ahn, J.H. J. Org. Chem., 1994, 59, 3490 c&3
17Br
\ 0I
96%
MeSCHzCl, AlC13 CH2C12 , O°C
/
Olah. G.A.; Wang, Q.; Neyer, G. Synthesis, 1994, 276 PhSH, rt SPh Lee, S.B.; Hong,J.-I, Tetrahedron
tett., 1995, 36, 8439
RelatedMethods:Section123(EthersfromAlcohols).
SECTION
131:
ETHERS, EPOXIDES FROM HYDRIDES
AND THIOETHERS
PIFA = phenyliodine(III)bis(t.rifluoroacetate) Kita. Y,; Takada,T.; Mihara, S.; Tohma,H. Synlett, 1995, 211
SECTION
132:
ETHERS, EPOXIDES FROM KETONES
Tsai. Y-M,; Tang,K-H.; Jiaang,W-T. Tetrahedron
AND THIOETHERS
Lett., 1993, 34, 1303
88%
162
Compendium of Organic Synthetic Methods, Vol. 9
PA,,
TBAF
Capperucci,A.; moceai. A. Tetrahedron
Section 134
A; Ferrara,M.C.; Bonini, B.F.; Mazzanti, G.; Zanti, P.; Ricci,
Lett., 1994, 35, 161 0
/oAc,
Rh2(Ok)4
*
PhF , 10h b
Pirrun~.M.C,; Lee,Y.R. Tetrahedron
0
69%
Lett., 1994, 35, 6231
RelatedMethods:Section124(Epoxidesfrom Aldehydes).
SECTION
133:
ETHERS, EPOXIDES FROM NITRILES
AND THIOETHERS
NO ADDITIONAL EXAMPLES
SECTION
134:
ETHERS, EPOXIDES FROM ALKENES Asymmetric
AND THIOETHERS
Epoxidation
-00
Ph \ -c
/N-O
, NaOCl +
Mn-salenderivative O°C , pH 11.3
&
58% (77% ee)
Chang,S.; Lee, N.H.; bobsen. m
J. Org. Chem., 1993, 58, 69 39
Mn (salen)catalyst , lh 1%H202, O°C, CH2C12 Schwenkreis, T.; Berkessel,A, Tetrahedron Lett., 1993, 34, 4785
CO2Et
Section 134
Ethers from Alkenes
threitol-strapped iodosylbenzene
Mn-porphyrin
163
, CH$I;!
t
A0
Ph-
, 1,Sdicyclohexylimidazole
86% (69% ee, R+) J.P,; Lee, V.J.; Zhang, X.; Ibers, J.A.; Brauman, J.1 J, Am. Chem. Sot., 1993, 115,
Collman. 3834
l
chloroperoxidase H202
,Bu
, acetone
Bu
9pH 5
----+v
0
78% (96% e-e, 2R3S) Allain, E.J.; Hager, L.P.; Deng, L.; Jacobsen, E.N. J. Am. Chem. Sot., 1993, 115, 4415 Me02%,, Ph Me02C
I
s
Ph
,B-OMe
0 0
t-BuOOH Manoury, E.; Mouloud,
H.A.H.; Balavoine, G.G.A, Tetrahedron
35% (22% ee , S,S) Asymmetry, 1993, 4, 2339
Mn salen catalyst, 02 PhH,rt
51% (52% ee) T.; Yamada, T.; Nagata, T.; Imagawa, IS. Chem. Lett., 1993,327
Mukaiyama,
-0 Ph )=/ Ph
Ph 32 \
0 Ph
/N-o
* cat. Mn salen, O°C , buffered bleach , pH 11.3
)\7/ Ph
0
69% (93% ee, S,S) Brandes, B.D.; &obss
J. Org. Chem., 1994, 59,4378 cat. Mn(salen) , CH2C12 -
phN
,,yp (42%ee, lS,2S)
Pietikainen.
P, Tetrahedron
Lett., 1994, 35, 941
49%
164
Compendium of Organic Synthetic Methods, Vol. 9
\m I/
Section 134
\ I/ 02
Mn salen catalyst, PhIO , O°C
0
72%(98%ee)
Sasaki,H.; Irie, R.; w.
T, Synlett, 1994, 356 2 PhIO, Mn salencatalyst
ph-
t
Ph
Sasaki,H.;Irie, R.; Hamada,T.; Suzuki,K.; mki. Mn salencatalyst, t-BuCHO PhA
“TPh
rt T, Tetrahedron,
27%(15%ee, lR2R) 1994, 50, 11827
w
02,fl
28% (63:37 cis:trans) 80% eefor cis Nagata,T.; Imagawa,K.; Yamada,T.; Mukaiyama,T. Chem. Lett., 1994, 1259
02, Mn salencomplex, rt NM1 , pivaladehyde, PhF
78%(63%ee) T,; Imagawa,IS.; Nagata,T.; Mukaiyama,T. Bull. Chem. Sot. Jpn., 1994, 67, 2248
B.
Mn (salen)catalyst, Bu4NIO4 imidazole, rt ,3h
Ph
53%(47%ee, lR,ZS (-) )
. . ..*
Pletlkamen.
Tetrahedron
c \
I
Lett., 1995, 36, 319
20%4-Ph-pyridineN-oxide, O°C 5%Mn salencomplex, CH2C12
/
Bran&s, B.D.; Jacobsen. E.N, Tetrahedron Lett., 1995, 36,5123
Section 134
Ethers from Alkenes
Ph-
165
8% Mn salen complex , mcpba , NM0
0
*
Ph4l
CH2C12, -78OC
89% (86% ee) Palucki, M.; McCormick, G.J.; Jacobsen. E.N, Tetrahedron
Lett., 1995, 36, 5457
chloroperoxidase , KOAc , Hz02 Ph
antifoamA, aq.acetone,pH 5.2 sodiumcitrate
*
Ph4
1111l111
0
89%(49%ee) Dexter, A.F.; Lakner,F.J.; Campbell,R.A.; Hager.L.P,J. Am. Chem. Sot., 1995, 117, 6412
a3 \
I
NT.;
02 , Mn salencatalyst, t-BuCHO
/
70%(64%ee) Imagawa,K.; Yamada,T.; Mukaiyama,T. Bull. Chem. Sot. Jpn., 1995, 68, 1455
Non-Asymmetric
Epoxidation
BIPA , FeCl2,02 70°C, Id
mo.
BIPA = N,N’-bis(2-(4-imidazoloyl)ethyl)-2,6-pyridinecarboxamide TJ Moriuchi, T.; Mikami, S.; Ikeda, I.; Ohshiro,Y. Tetrahedron Lett., 1993, 34, 1031 cat. [K-lO-montmorilloniteNi(acac)] 0
iBuCH0 , CH2C12,rt autoclave,10bar Bouhlel,E.; m. P,; Levart, M.; Montaufier, M-T.; Singh,G.P. Tetrahedron Lett., 1993, 34, 1123 -0. P,; Levart, M. Tetrahedron L&t., 1993, 34, 1127
ph*Ph
[CoCl&licylaldehyde-L-serinemethylester] w 02,MeCN,rt,25h
Punniyamurthy,T.; Bhatia,B.; j,qbal.J, Tetrahedron Lett., 1993, 34,4657
‘“TPh 64%
67%
166
Compendium of Organic Synthetic Methods, Vol. 9
h
Fecat.,02,iPrCHO,rt
R.W,; Reihs,S.; Hug, M. Tetrahedron
alfrank.
Section 134
* pgF+ e,
Lett., 1993,
34,
96%
Ph
6033
10%(NH&H4PV6W&4v6 H20 02, DCE,25OC, 4h 2 eq.iPrCH0 77% Hamamoto,M.; Nakayama,K.; Nishiyama,Y.; Ishii. Y, J. Org. Chem., 1993, 58, 6421
P
Co(mac)2,EtCH(OEt)z
C7Hl5
97%
02, MS481.,45OC
mat = 3-methyl-2,4-pentanedibne Mukaiyama,T.; Yorozu, M.; Yakai, T.; Yamada,T. Chem. Lett., 1993, 439
0I msha.
.
CUE,
0
CH3CH0, CH2C12
02,rt, 17h
0
79% S.-I,; Oda,Y.; Naota,T.; Komiya, N. J. Chem. Sot. Chem. Commun., 1993, 139 urea-H202complexfmaleic acid =
BUN
Bu,/f
71%
Astudillo, L.; GaIindo.A,; Gonzalez,A.G.; Mansilla,H. Heterocycles, 1993, 36, 1075 1. [Mn*‘*(TPP)(Cl)], CHs12 I . O-D.;
0 2. imidazole, Bu@IO4,5h
Tangestaninejad, S. Tetrahedron Lett., 1994, 35,945
o= 0
, KHSO5 zc
+
H20KH2C12(pH 11) 18-crown-6,5”C w. .
(9 M,; Ito, S.; Tsutsumi,N.; M&&J,&
Tetrahedron
l
Mt.,
91) 80%
1994, 35, 1577
Section
167
Ethers from Alkenes
AgOAc/bipy/anode ACN (0.1 M LiCLO4) H20
Kandzia,C.; Steckhan. Tetrahedron
-%d
iPrCH0, Fe(AAEMA)3 p02
*
rt, 10h
(-)=, AAEMA =
87%
0
Mt., 1994, 35, 3695
00
Mastrorilli, P.; Nobile, C.F, Tetrahedron
Lett., 1994,
PhzP-‘-PPh, II
35, 4193 0
II
87%
* k=
Ph -LA,&;
0
0
F
Ph H202 Delair, P.; Blass,B.E. Tetrahedron Lett., 1994,35, 8123 S II
1.
EtOlPEt0
SBn
S
2. TBAF.3 H20 wG.;
82%
.
Mecichetti, S.; Neri, S.; Skowr0nska.A. Synlett, 1994, 267 NaOCl ,4-methylpyridine
hJ
P
w
PJ
88%
0
porphyrincatalyst/Mn ; Pereira,M.M.; Serra,AC.; Johns~&pe. R.A.W; Nunes,M.L.P.G. J. Chem. Sot., Perkin Trans. I., 1994, 2053
Y
YO~OZU. K;
Takai,
C7H
15
02 (1 atrn),2% Co(acac)z EtCH(OEt)2,45OC, 1Oh
> 48%
0 T.; Yamada,T.; Mukaiyama,T. Bull. Chem. Sot. Jpn., 1994,67, 2195
Compendium of Organic Synthetic Methods, Vol. 9
168
Section 134
Oxone, 0°C , Bu4NHS04 t
IOBn
acetone , CH-$&
OBn
, buffer 99%
Denmark.S.E,; Forbes,D.C.; Hays,D.S.; DePue,J.S.; Wilde, R.G. J. Org. Chem., 1391 M 0 ‘-x Fg 6
P
1995,
60,
, MeCN, O°C
> 15min Me Yang. DJ Wong, M.-K.; Yip, Y.-C. J. Org. Chem.,
1995,
60, 3887
CO2H \ I 2 US.;
0-J
hv , methyleneblue PhH , Hz0
/ \ Thanulingam,T.L.; Rajesh,C.S.; George,M.V. Tetrahedron
Chen,Y.; Beymond.J.-L, Tetrahedron Lett.,
1995,
Lett., 1995,
36, 1337
36,4015
t-B&OH, Ti(OiPr)d, SiO2 w rt, Id Fraile, J.M.; Garcia,J.I.; Mayoral. J,A,; deMhorval,
L.C.; Rachdi,F. J. Chem. Sot. Chem.
Commun., 1995,539
PhIO, NaOCl, Mn salencatalyst t Rasmussen, KG.; Thomsen,D.S.; mn. 2009
w.
92%
K.& J. Chem. Sot., Perkin Trans. l., 1995,
Section 135
Ethers from Misc.
t-B&OH,
169
OH
MeOH
CrS-2- molecular sieve
85%
. Joseph, R.; Sasidharan, M.; Kumar. R... Sud& . A... Ravmdmnathu Commun.,1995,134l
Formation
0
Bosman,C.; DA-ale.
of Other Ethers
PhSeSePh , CAN I
J. Chem. Sot. Chem.
MeOH ,30 min
-c,
A; Resta,S.; Troeolo. C, Tetrahedron
SePh 93% “%, OMe
Lett., 1994, 35, 6525
97%
Marshall. J.A,; Sehon,C.A. J. Org. Chem., 1995, 60, 5966 REVIEW:
“RationalDesignof Manganese-Salen EpoxidationCatalyts;PreliminaryResults,”Hosoya, IV.; Hatayama,A.; Irie, R.; Sasaki,H.; Katsuki.T, Tetrahedron, 1994, 50, 4311
SECTION
135:
ETHERS, EPOXIDES AND THIOETHERS FROM MISCELLANEOUS COMPOUNDS PhSSPh, SbC15,DCE OMe
w
PhS-(=)-OMe
reflux ,3h 76% Mukaiyama, T.; Suzuki, K. Chem. Lett., 1993, 1 LiAlH4, Tic14 PhSOzMe w 93% PhSMe Akgiin, E.; Mahmoud,K.; Mathis. C.% J. Chem. Sot. Chem. Commun., 1994, 761
170
Compendium of Organic Synthetic Methods, Vol. 9
\r’u S
[SiO2/SOCl2] 10min
-
‘rs\y
73%
Mohanazadeh. F,; Momeni, A.R.; Ranjbar,Y. Tetrahedron Lett., 0 II
Section 135
1994,
35,6127
CpzTiC12,Sm, THF , rt w
Ph/‘\Me Zhann. Y,; Yu, Y.; Bao, W. Synth. Commun., 0 II
Ph”‘\ Ph Wang, J.Q.; Zhanrr, Y.M,Synth.
1995,
77-88%
25, 1825
TiC14,Sm, THF , rt ,30 min Commun., 1995,
Ph/‘\Me
25, 3545
w
Ph”,
Ph
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
Section 138
CHAPTER
10
PREPARATION SULFONATES
SECTION 136:
171
Halides fkomAlcohols
OF HALIDES
AND
HALIDES AND SULFONATES FROM ALKYNES NO ADDITIONAL EXAMPLES
SECTION 137:
HALIDES AND SULFONATES FROM ACID DERIVATIVES PhIO , NBS , MeCN , 60°C *
Ph-C02H
Ph+Br 73%
Graven, A.; a
SECTION 138:
(96:6 cis:trans)
K& Dahl, S.; Stanczdc,A. J. Org. Chem., 1994, 59, 3543
HALIDES AND SULFONATES FROM ALCOHOLS AND THIOLS
PPh3, (C13COCh0 w PhCH2Cl PhCHzOH Rivero, I.A.; SomanatXlan.; Hellberg, L.H. Synth. Commun., 1993, 23, 7 11
1
95%
BBr~,CH$ld)°Cw < .
Pelletier, J.D.; poiu
Tetrahedron L&t., 1994, 35, 1051
TMSCl , DMSO wh7-4H
&y&
D.C, J. Org. Chem., 1995, 60, 2638
t
c$H 1741
95%
172
Compendiumof Organic Synthetic Methods, Vol. 9
o-
OH
12, pet ether, reflux , 1.5h
Section 142
42%
I
Joseph,R.; Pallan, P.S.; Sudalai, A.; bvindranathm. T, Tetrahedron Left., 1995, 36, 609 Me$iCl , BiC13 OH
rt ,90 min f Labrouihere, M.; Le Roux, C.; Oussaid,A.; Gaspard-Boughmane,H.; Dubu
quant. Bull. Sot.
Chim. Fr., 1995, 132, 522
REVIEWS:
“An Alternative Synthesisof Aryl and Heteroaryl Bromidesfrom Activated Hydroxy Compounds,” IQ&&&y. A.&; Li, J.; Stevens, C.V.; Ager, D.J. Org. Prep. Proceed. int., 1994, 26,439
SECTION 139:
HALIDES AND SULFONATES FROM ALDEHYDES NO ADDITIONAL EXAMPLES
SECTION 140:
HALIDES AND SULFONATES FROM ALKYLS, METHYLENES AND ARYLS
For the conversionR-H + R-Halogen,seeSection 146 (Halides from Hydrides). 2 eq. VO(OEt)CZ2,N2 MeCN , O°C+ rt Ph~si~3
*
PhwC1
6oo/ 0
Fujii, T.; Hirao. T,: Ohshiro. Y, Tetrahedron Lett., 1993, 34, 5601
SECTION 141: HALIDES AND SULFONATES FROM AMIDES NO ADDITIONAL EXAMPLES
SECTION 142: HALIDES AND SULFONATES FROM AMINES 1. TolSO~l 2. base PheNH2
3.NBS,THF,hv
Ph-
Br
86% Collazo. J&; Guziec Jr., F.S.; Hu, W.-X.; Pankayatselvan,R. Tetrahedron Lett., 1994, 35, 7911
Section 146
Halidesfrom Hydrides
173
SECTION 143: HALIDES AND SULFONATES FROM ESTERS NO ADDITIONAL EXAMPLES
SECTION 144:
HALIDES AND SULFONATES FROM ETHERS, EPOXIDES AND THIOETHERS NO ADDITIONAL EXAMPLES
SECTION 145:
HALIDES AND SULFONATES FROM HALIDES AND SULFONATES n-CgH17I, KF , GUI
CICF~02Me
-
C&I&F3
Cd12, HMPA , 120°C, 8h
Chen. Q-Y,; Duan, J.-X. Tetrahedron Lett., 1993, 34, 4241
SECTION 146:
+ CO2 + MeCl
77%
HALIDES AND SULFONATES FROM HYDRIDES
a-Halogenationsof aldehydes,ketonesand acidsare found in Sections338 (Halide-Aldehyde),369 (Halide-Ketone),359 (Halide-Esters)and 319 (HalideAcids).
BrF3, Br2 , O*C
Br Rozen, S,; Lerman, 0. J. Org. Chem., 1993, 58, 239
t
OMe
BP-(=)-OMe
CH2C12,MeOH 90% Bisawa. SC,; Rao, R. Synth. Commun., 1993, 23, 779
(t
PyH Br3, THF NJ32
\--I/
&eves.
W.P,; King II, R.M. Synth. Commun., 1993, 23, 855
87% (19:68 o:p)
Section 147
Compendium of Organic Synthetic Methods, Vol. 9
174
-
NBS/cat. HZSM-5 OMe
cc4
XeF2, MeCN ,25OC, 6h /
CHO
FQ
CHO
I H Wang, J.; Scott. AJ, Tetrahedron Lett., 1994, 35, 3679
’c’ \-/
I H
NH4VO3, H202, KBr 2 phase (H201CHCl3) ,25OC
*
35%
/- \ \r *
50%
Bf
\/ 9 9 0
Conte, V.; Di Furia. F,; Moro, S, Tetrahedron Lett., 1994, 35, 7429 I2
I
Qm03)2
I
CH2C12
52%
20°C , 14h
Bachki, A.; Foubelo, F.; Yus, M, Tetrahedron, 1994, SO, 5139
(t (t
HgO-120, CHg12 OBn *
\/
&jto.
$=)-OBn
87%
L; Hatakeyama, T.; Takeo, M.; Suginome, H. Synthesis, 1995, 1273 NBS , AcOH , ultrasound, 6h OMe * ..~-(=)-OMe
\/
92%
Paul, V.; Sudalai, A.; Daniel, T.; Srinivasan. K,V, Synth. Commun., 1995, 25, 2401
SECTION 147:
HALIDES AND SULFONATES FROM KETONES CF2Br2,Zt-t
IL
F
u. C.-M,; Qing, F.-L.; Shen, C.-X. J. Chem. Sot., Perkin Trans. l., 1993, 335
Section 150
Halides from Misc.
175
SECTION 148: HALIDES AND SULFONATES FROM NITRILES NO ADDITIONAL EXAMPLES
SECTION 149:
HALIDES AND SULFONATES FROM ALKENES
For halocyclopropanations,seeSection 74E (Alkyls from Alkenes). HCl , SiO2 Cl 62% 0 Kn]DD. P.J,; Daus, K.A.; Tubergen, M.W.; Kepler, K.D.; Wilson, V.P.; Craig, S.L.; Baillargeon, M.M.; Breton, G.W. J. Am. Chem. Sot., 1993, 115, 3071
0I
ma.
F
KHF2 , SiF4, rt
79%
M; Shibakami, M.; Kurosawa, S.; Arimura, T.; Sekiya. pb,J. Chem. Sot. Chem.
Commun., 1995, 1891
SECTION 150:
Ph-
N=N-N
HALIDES AND SULFONATES FROM MISCELLANEOUS COMPOUNDS
3
12, CH212,80°C ,4h
w
Ph-I
>98%
Wu, 2.; Jvfoare; J& Tetrahedron Lett., 1994, 35, 5539
m
S
S
Fz,Iz,MeCN,rt +
db ‘\
Chambers.;-;
I’
L /\
F
I’
52% Atherton, M. .I. Chem. Sot. Chem. Commun., 1995, 177
SOC12,DMF , 100°C 81% C~H25S03Na w325Cl Carlsen, P.H.J.; Rist, 0.; Lund, T.; Helland, I. Acta Chem. Stand. B., 1995, 49, 701
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
176
Section 153
Compendium of Organic Synthetic Methods, Vol. 9
CHAPTER
11
PREPARATION
OF
HYDRIDES
This chapter lists hydrogenolysis and related reactions by which functional groups are replaced by hydrogen: e.g. RCH2X + RCH2-H or R-H.
SECTION
151: HYDRIDES
FROM
ALKYNES
NO ADDITIONAL
SECTION
152: HYDRIDES
FROM
EXAMPLES
ACID DERIVATIVES
This section lists examples of decarboxylations (RC02H + R-H) and related reactions. NO ADDITIONAL
SECTION
153: HYDRIDES
FROM
EXAMPLES
ALCOHOLS
AND THIOLS
This section lists examples of the hydrogenolysis of alcohols and phenols (ROH + R-H). 1. (Bu3Sn)p, To1 , reflux , Id (90%)
QH2hoH
2.2 eq. EtNCO
3. Et$iH , PhH , 140°C 0.05M , benzoyl peroxide (70%) Nishivama. K,; Oba, M.; Ishimi, M.; Sugawara, T.; Ueno, R. Tetrahedron
Ph-OH
1. [PPh3/rf20] , CH2C12 2. NaBH4, rt
3.1NHCl Hendrickson. JB,; Singer, M.; Hussonin, Md.S. J. Org. Chem.,
Wustrow. D.J%;Smith III, W.J.; Wise, L.D. Tetrahedron
* 1993,
ktt.,
1993,
Phn 87% 58, 6913
L&t., 1994, 35, 61
34, 3745
Section 157
Hydrides from Amines
H u;
Cusack, K.P.; Kwochka,
H W.R. Tetrahedron Lett., 1994, 35, 1477
PPh3, Et.$IBr , MeCN
CH3-(CHd9-QH
177
*
e’
C&---W2)g---H
94% Maeda, H.; Maki, T.; Eguchi, K.; Koide, T.; Qhmori. H, Tetrahedron Lett., 1994, 35,4129 CBH17-OH
1. MeCON=C=S
w C8Hl~ 2. Ph$iH , AIBN , 80°C, 10 min
48~83%
Oba, M.; Nishivama, K, Synthesis, 1994, 624 Also via: Section 160 (Halides and Sulfonates).
SECTION
154: HYDRIDES
FROM
ALDEHYDES
For the conversion RCHO + R-Me, etc., see Section 64 (AIkyls from Aldehydes). NO ADDITIONAL
SECTION
155:
HYDRIDES FROM AND ARYLS NO ADDITIONAL
SECTION
156: HYDRIDES
FROM
EXAMPLES
ALKYLS,
METHYLENES
EXAMPLES
AMIDES
NO ADDITIONAL EXAMPLES
SECTION
157: HYDRIDES
FROM
AMINES
This section lists examples of the conversion RNH2 (or R2NH) -+ R-H.
e- , TI-IF/HzO ,60% HNO3 67%
Tpfii. S,; Okumoto, H.; Satoh, H.; Minoshima, T.; Kurozumi, S. SynZett, 1995, 439
178
Compendium of Organic Synthetic Methods, Vol. 9
SECTION
158: HYDRIDES
FROM
Section 158
ESTERS
This section lists examples of the reactions RC02R’ + R-H and RCO2R’ + R’H, HO \\
+ UT.;
Pd(acac)z , PBu3 , rt PhH ,3h
.
(alkyne:allene = 99: 1)
CSh7
Matsumoto, T.; Kawada, M.; Tsuii. J, Tetrahedron
$=
J$
SMe
H
*
II other initiators
34, 2161
hv (tungsten lamp) Bu$nH , 0°C
S
l-BflqSi()i
Lett., 1993,
f-l
I
34,
2733
u-o’Ny
were .also used
Barton, D.H.R.; parekh. S&; Tse, C.-L. Tetrahedron
Lett., 1993,
SMe 5 eq. PhSiH3, AIBN
toluene , reflux , lh Barton, D.H.R.; Jang, 0.0.; Jaszverenyi, J.Cs. Tetrahedron,
43
quant.
1993, 49, 2793, 7193
dcoxygenated cyclohexane AIBN , 80°C 99% Gimisis, T.; Ballestri, M.; Ferrer-i, C.; Chatgilaloglu. C,; Boukherroub, R.; Manuel, G. Tetrahedron
Lett., 1995, 36, 3897
Section 160
Ph
4
AC
TBAFex Hz0 , NM0 , THF , rt 1,3-propanedithiol Ph
Ph Ph
w 0
0 Uelo. M4; Okamura, A.; Yamaguchi, J. Tetrahedron
SECTION
179
Hydrides from Halides
HYDRIDES FROM THIOETHERS
159:
99%
Lett., 1995, 36, 7467
ETHERS,
This section lists examples of the reaction R-O-R’ +
Me Hamel. P,; Zajac, N.; Atkinson, J.G.; Girard, Y. Tetrahedron
EPOXIDES
AND
R-H.
Lett., 1993, 34, 2059
5 eq. Ni2B , MeOH-THF t
C 11H23-S-Ph
I
2 NiBr2+
6 NaBH4
__I_)
Ni2B
90%
c 1 lH24
I
Back. T.G,; Baron, D.L.; Yang, K. J. Org. Chem., 1993, 58, 2407
0
DMN* , ascorbic acid , iPr0H hv,3h
SePh &Q&Y.
DMN*
= photoactivated
*
a=’
1,5-dimethoxynaphthalene
85% Cr,; Rao, K.S.S.P.; Sekhar, B.B.V.S. J. Chem. Sot. Chem. Commun., 1993, 1636
SECTION
160:
HYDRIDES
FROM
HALIDES
AND SULFONATES
This section lists the reductions of halides and sulfonates, R-X + R-H.
57% HI, 25OC, 15 min
98%
Wll Wll
Br Penso. M,; Mottadelli,
S.; Albanese, D. Synth. Commun., 1993, 23, 1385
180
Compendium
of Organic Synthetic Methods, Vol. 9
Section 160
Br\ MeLi,
THF , -105OC
52%
b-
Br
% Grandjean, D.; pale. P, Tetrahedron
L&t., 1993, 34, 1155
M+ B:i,-,:::“;HcHLH OCH2CH2CH2Br
2
an aryl
translocation
24% Lee. EJ Lee, C.; Tae, J.S.; Whang, H.S.; Li, KS. Tetrahedron
2
2
C3H7
61% Lett., 1993, 34, 2343
OH Cl
C
w
w
H
Cl
NaBHz(OCH2CH20Meh
Cl
NiCl2, MeOCHzCHzOH THF ,68OC, 2h
\
I
Cl Tabaei, S.H.; Pittman Jr.. CU, Tetrahedron
I
/
-4
Lett., 1993, 34, 3263
HC02H , Pd/C , toluene H20, NazCO, , 90°C Cl Cl Barren. J-P,; Baghel, S.S.; McCloskey,
quant. P.J. Synth. Commun., 1993, 23, 1601
PVP-PdC12, H2, 65OC ambient pressure , EtOH , NaOH PVP-PdC12 = palladium anchored on poly(N-vinyl-2pyrrolidinone) Zhang, Y.; Liao. S,; Xu, Y. Tetrahedron Lett., 1994, 35, 4599
0 \
I
/
quant.
Section 162
cti
181
Hydrides from Ketones
borohydride exchange resin , rt ,3h 0.1 Ni(OAc), , MeOH
17---Bf
Yoon. N.m, Lee, H.J.; Ahn, J.H.; Choi, J. J. Org. Chem.,
.
&I&I.
U,; Sanna, K.D. Tetrahedron
SECTION
161: HYDRIDES
Lett., 1994,
FROM
35,
*
CSH 17-H quant. 59, 4687
1994,
7861
HYDRIDES
NO ADDITIONAL EXAMPLES
SECTION
162: HYDRIDES
FROM
KETONES
This section lists examples of the reaction R2C-(C=O)R Et3SiH , BF3mOEt2, CHg12
+ R2C-H.
*
ph-
Ph mu.
Ph 92%
L Synth. Commun., 1994, 24, 1999
NaBHgN
, BFpOEt2, THF *
rt, 12h
‘(+(=)--c
130--(=)-\ 94%
Srikrishna. A,; Sattigeri, J.A.; Viswajanani, R.; Yelamaggad, C.V. Synlett,
1995,
93
OzC02Me
OH
1. ClC02Me
A
2, NaBH3
OH
I -OH 94x76%
. ltw. 36,5335
D,; Doecke, C.W.! Hay, L.A.; Koenig, T.M.; Wirth, D.D. Tetrahedron
Lett., 199%
182
Compendium
NHc~Me
of Organic Synthetic Methods, Vol. 9
1. Me$iCl
Section 165
NHCO2Me
, NEt3
2. Et$iH , Tic13 PhAA b Ph &CO,H ma--I Yato, M.; Homma, K.; Jshida. A, Heterocycles, 1995, 41, 17
NaCNBH3, THF BFyOEt;!, rt ,30 min 4
g5%
+
Me0 shna. A,; Viswajanani,
SECTION
.. 2) 85% (3 R.; Sattigeri, J.A.; Yelamaggad, C.V. Tetrahedron
163: HYDRIDES
FROM
SmI2, THF-HMPA
1995,
36,
NITRILES
This section lists examples of the reaction, R-C=N + isonitriles (R-N&). CN
tiff.,
R-H (includes reactions of
Ph
, 0°C
CN 97%
CN Ph 3 Hong, W.S.; Cho. Y.S,; Koh, H.Y. Tetrahedron Lett., 1995,
SECTION
164: HYDRIDES
FROM
ALKENES
NO ADDITIONAL
SECTION
165: HYDRIDES
FROM
H 36, 7661
EXAMPLES
MISCELLANEOUS
COMPOUNDS
Mg , EtOH , cat. HgCl2 P
rt
Lee, G.H.; Choi, E.B.; Lee, E.: Pak. C& Tetrahedron
98% Lett., 1993, 34, 4541
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
Section 166
Ketones from Alkynes
CHAPTER
183
12
PREPARATION
OF KETONES
SECTION 166: KETONES FROM ALKYNES
Cha. JS,; Min, S.J.; Kim, J.M.; Kwon, 0.0. Tetrahedron Lett., 1993, 34, 5113
. Tekeuchl.,
78% Yasue, H. J. Org. Chem., 1993, 58, 5386
MeCN , 760°C, 4h OMe CO)sCr
+ Me
(11:l ,33%) Kim, O.K.; 1;vulff. W.D%; Jiang, W.; Ball, R.G. J. Org. Chem., 1993, 58, 5572 0
Ph 1.10% c02(c0)8,
DME
2.20% P(OPh)3 , reflux
Iwasawa, N.; Matsuo, T. Chem. Lett., 1993, 997
0
Compendiumof Organic Synthetic Methods, Vol. 9
Section 167
1. BrzBH*SMez 2. propylene glycol Br
X
Bu
* 3. CH2=CHCH2MgCl, THF , -78OC 4. HMPT , THF , 50°C, HMPA 5. oxidation Brown. H.r; Soundararajan,R. Tetrahedron Lett., 1994, 35,6963
Bu* 95%
MeReO3, H202, tOH Ph
=
Ph
*
Ph
Ph 4f 0
80%
Zhu, 2.; EsPenson.J.ltI, J. Org. Chem., 1995, 60, 7728
SECTION 167: KETONES FROM ACID DERIVATIVES
P
Ph
pAc1 TiCl&Zn ,3% HCl
-
p)$+;
+p;)=(;
69%
24%
Shi, D.; Chen, J.; Chai, W.; men. W,; Kao, T. Tetrahedron Lett., 1993, 34, 2963 1. (C6h3)2Zn
2. CuCN.2 LiCl
98%
Langer, F.; Waas,J.; -eI. Cl
P, Tetrahedron Lett., 1993, 34, 5261 e’ , Bu@3F4, rt
)
PTPh
80%
meCN 0 0 st. J.-C,; Pereira-Martins, E.; Troupel, M.; Perichon, J. Tetrahedron Lett., 1993, 34, 7571 1. (Me2N=CHCl)Cl, Py MeCN/THF 2 5eq NaN3 O°C * Pa 3:oYG rt ’ Affandi, H.; Bayguen, A.V.; J&&&W, Tetrahedron Lett., 1994, 35, 2729 pt(\/co2H
90% N3
185
Ketonesfrom Acids
Section 167
Me0 CgHllCOOH , (PhCO)20, Id 20% (Sic14+ 3 AgC104) CH2C12,rt Me0 T, BUZZ.Chem. Sot. Jpn., 1993, 66, 3729
Kitagawa, H.; m
&Z&&K.;
a
Ph
BU’n*SnBu3 Cl
Ph
Pd(PPh& , dioxane 100°C, 30 h
*
Ph+ 50%
0
Echavarren. A.M,; Perez,M.; CastaiIo, A.M.; Cuerva, J.M. J. Org. Chem., 1994, 59, 4179
0
1. (Ph0)2PON3, NEt3 dioxane , reflux 2.2 M HCl
t
?m
HW 0 w;
61% (2.83 cis:trans) Cowell, J.K.; Harris, L.J. Tetrahedron Lett., 1994, 35, 3883
.
0I \ 0
t-BuCl/Li/ ultrasound Liofl
, THF
76% Aurell, M.J.; Einhom, C.; Einhom, J.; Luche. J.L. J. Org. Chem., 1995, 60, 8
PhC02Li
iPrC1, Li , THF , ultrasound, rt
*
63% ’ Aurell, M.J.; Danhui, Y.; Einhom, J.; Einhom, C.; Luche, J.L, Synlett, 1995, 459
186
Compendiumof Organic Synthetic Methods, Vol. 9
P
OH
NaI04, MeOH, TEBA
Phx
CO2H Kore, A.R.; Sagar,A.D.; &&&&. 0
92% * DB-18-c6 Ph-L Ph M.m Org. Prep. Proceed. Int., 1995, 27, 373
Ph
* Cl
Han, Y.; Fang, L.; Tao, W.-T.; m.
Cl
0
[PhJGaBuJLi, THF-hexane , 0°C
4f
Cl
Section 168
82%
Ph
Y.-Z4 Tetrahedron Lett., 1995, 36, 1287
Ph
PhMgBr , CuBr , LiBr , THF , 0°C
0
Ph
75%
0
Babudri, F.; Fiandanese,V.; Marchese.G; Punzi, A. Tetrahedron Lett., 1995, 36, 7305
m.
a
EtMgBr , Ni(dppe)Clz 70%
Ph * Cl PhL C,; Aronica, L.A.; Lardicci, L. Tetrahedron Lett., 1995, 36,9185
SECTION 168: KETONES FROM ALCOHOLS AND THIOLS 0.2% his-Ru catalyst, THF 65OC 99% w BackvaIl, J.-E.; Andreasson,U. Tetrahedron Lea., 1993, 34, 5459 1. t-B&OH, H+ *
Ph
2. DBU
80x58% Antonioletti, R.; Arista, L.; Bonadies, F.; Locati, L.; 8cett.t-i.A, Tetrahedron Lett., 1993, 34, 7089 !
1. RuC13.nHz0 , Co(OAch.4 Hz0 2. ;i;k-;,&Ho, 2o”c =c )
Murahashl.. S.-L; Naota, T.; Hirai, N. J. Org. Chem., 1993, 58, 7318
89%
187
Ketonesfrom Alcohols
Section 168
L
H
0.05 Cr03 ,3 eq. 70% t-BuOOH
96%
CH2C12, rt
Ph Muzaft.1; Ajjou, ANA. Synthesis, 1993, 785 0
1. Co(Imd)2 , EtOAc Ph Ph P LH 2. imidazole , CH2C12 0 68% S.-L; Park, D.-C.; Rho, H.-S.; Han, S.-M. Synth. Commun., 1993, 23, 2219
d
OH PDC , Celite , CH2C12
\
I
25OC, Id
/
55%
Bijoy, P.; Subba Rao. G.S.R,Synth. Commun., 1993, 23, 2701 Cal37
PhI=O ,;(NO&
, DCE
z&l37
OH aldehydescan also be formed quant. Yokoo, T.; Matsumoto, K.; Oshima. K.: UtimoK. Chem. Lett., 1993, 571
(t
V205 , Z1-02, toluene 0
OH llO°C, 6h
-o=
aldehydescan also be formed Nakamura, H.; Matsuhashi, H.; Arata, K. Chem. L&t., 1993, 749
-Q5
88%
5% CoSANSE, MeCN 60070°C, 02, 17h -
-Q+
CoSANSE = ~is(salicylidene-N-(methyl-3-hydroxypropionate))] Co Punniyamurthy, T.; Iabsl. Tetrahedron Lett., 1994, 35, 4007
0
72%
188
Compendium of Organic Synthetic Methods, Vol. 9
Phi ,3% Pd(OAc)2, DMF
Section 168
Ph+O
w
3 eq. KOAc , 80°C, 3d
40%
Larock. RC,; Yum, E.K.; Yang, H. Tetrahedron, 1994, 50, 305
9 02
OH
(t
0
79%
CoSANSE * o= CoSANSE = chiral cobalt catalyst IQ&a, S.J.S.; Punniyamurthy, T.; Iqbal. J, Tetrahedron Lett., 1994, 35,4847
9 J+ z
t-B&OH, EhNOH , rt [OsO4] , aq. t-BuOH ,
fi
HO
i k
1 OH Beck, C.; Seifert. & Tetrahedron Lett., 1994, 35, 7221 0.5% Ru complex ,20% Co complex 0.5 02 , toluene , 1OOOC,36h 87% 2,5-dit-butyl-1,4-benzoquinone
0 OH Wang, G.-Z.; Andreasson,U.; Backvall. J.-E, J. Chem. Sot. Chem. Commun., 1994, 1037 cat. PdC12, cat. Adogen 464 9.3h, Nag03 , DCE , reflux
A&Mohand,
t-B.=-(-}=O
also for primary alcohol + aldehydes S.; Henin, F.; Muz . J, Tetrahedron Lett., 1995, 36, 2473
“;;;;t”,;OAc
)
t-B+(-)=0 96%
Murahashi. S-I,; Naota, T.; Oda, Y.; Hirai, N. Synlett, 1995, 733
189
Ketonesfrom Aldehydes
Section 169
OH Co(acac)3,02, MeCN ,75’C
93% O Iwahama, T.; Sakaguchi,S.; Nishiyama, Y.; Ishii. Y, Tetrahedron Lett., 1995, 36, 6923
6D
Bacillus stearothemophilus
‘4 %
heptane
*
64
0 49% 100%ee (lS,SR) Fantin, G.; Fogagnolo, M.; Giovannini, P.P.; Medici. A; Pedrini, P.; Poli, S. Tetrahedron Lett., 1995, 36, 441 OH
‘OH
0
cat. CoC12(PPh& , t-BuOOH /
93%
DCE , heat, 4.5h
Ph
aldehydescan also be formed Dyer. &; Varghese, J.P. Synth. Commun., 1995, 25, 2261 H
L
e’ , RuO2, aq. MeCN , Bu,$JOH
89%
Bu$JBr Ph Torii, S.; Yoshida, A. Chem. Lett., 1995, 369 RelatedMethods: Section48 (Aldehydesfrom Alcohols and Phenols).
SECTION 169: KETONES FROM ALDEHYDES
0.05 Rh(R-BINAP)ClOd CH2C12,rt ,30 min
(3
97) 81% (>99%ee3S,4S)
Wu, X.-M.; Funakoshi, K.; Sakai. K, Tetrahedron Lett., 1993, 34, 5927
190
Compendium of Organic Synthetic Methods, Vol. 9
Section 169
71% Punniyamurthy, T.; Kalra, S.J.S.; Qbal. J, Tetrahedron Lett., 1994, 35, 2959
PhCHO
1. t-BuMe$iCBrzLi 2. set-BuLi
, -78OC + rt
3. PhCHO 4. HMPA Shinokubo, H.; Oshima. K.: IJtimotu
0
*
PhkPh
5g%
Tetrahedron Lett., 1994, 35, 3741
59% (78% ee , S) Barnhart, R.W.; Wang, X.; Noheda, P.; Bergens, S.H.; Whelan, J.; Bosnich.B,. Am. Chem. sot., 1994, 116, 1821 Me$iCBr3
PhCHO
, CrBq/LiAlHq
THF , 60°C
mn.
D.M.; Comma, P.J. Synlett, 1994, 663
PhCHO CH(OEt)3, H+ , THF
Katritzkv.
2. BuLi, THF , -78OC 94% 3. EtBr 4. H+ A.R,; Lang, H.; Wang, 2.; Zhang, 2.; Song, H. J. Org. Chem., 1995, 60, 7619 C&I $xCpCl
,20% ZnBr2
PhCHO
*
PhCHO *
THF ,3h ,25OC Zheng, B.; Sreb&
M, J. Org. Chem., 1995, 60, 3278
Section 171
Ketones from Amides
SECTION 170:
191
KETONES FROM ALKYLS, METHYLENES AND ARYLS
This section lists examples of the reaction, R-CH2-R’ -3 R(C=O)-R’. 5% CoSANSE , MeCN Ph-
t
Ph
cat. 2-oxocyclopentene carboxylate 60°C, 15h, O2 CoSANSE = ~is(salicylidene-N-(methyl-3-hydroxypropionate))] Co Punniyamurthy, T.; IabaI. J, Tetrahedron Lett., 1994, 35, 4003
t’h
69%
OMe OMe
A@, Me$YBF3 CH2C12, -78OC+ rt 76%
Kiselyov, A.S.; m.
R.G, Tetrahedron Lett., 1995, 36, 4005
SECTION 171: KETONES FROM AMIDES
Me\
N I OMe
OMe I N\ Me
0 1.2 eq. PhLi Ph +
2 . H+
Ph 4f
0
75% O
Sibi. M.P,; Marvin, M.; Sharma, R. J. Org. Chem., 1995, 60, 5016 1.2.2 BuLi , -78OC cN-(
,Ph
t 2. AcOH 3. K,C03,65°C
,.ji\
ph
82% Brandange, S.; Holmgren, E.; Leijonmarck, H.; Rodriguez, B. Actu Chem. &and. B., 1995, 49, 922
\ G
N-
1.2 eq. PhLi t
C02Et 2. H30+
Ph Prakash, G.K.S.; York, C.; Liao, Q.; Kotian, K.; Qlah. G.A, Heterocycles, 1995, 40, 79
95%
192
Compendiumof Organic Synthetic Methods, Vol. 9
Section 172
2 eq. EtAIC12, rt , 12h Ph Ph7
N I
56%
Ph
CH2Q
so2
Iwama, T. Tetrahedron Lett., 1995, 36, 245
-T.;
0
PhMgBr
PhK
68% Ph
. Kashlma. CJ Kita, I.; Takahashi, IS.; Hosomi, A. J. Heterocyclic Chem., 1995, 32, 25 REVIEW:
“Chemistry of N-Methoxy N-Methyl Amides. Applications in Synthesis.A Review,” S M.P. Org. Prep. Proceed. Int., 1993, 25, 5
SECTION 172: KETONES FROM AMINES 1. “X” 2. H30+
t
3 = H
40% X = octane,230°C ,2h X = t-BuOK./BuLi/THF/-50°C ,2h 73% Sprules, T.J.; Galpin, J.D.; Macdonald, D, Tetrahedron Lett., 1993, 34, 247
kc@7
9 W04 9ether 25OC, lh
Harris, C.E.; Lee, L.Y.; Dorr, H.; Singaram. B, Tetrahedron Lett., 1995, 36, 2921
75%
Section 174
Ketonesfrom Ethers
193
/OH o= % )<8Jf TS-1 , H202, acetone
N
0
reflux ,4h -o= TS-1 = zeolite titanium silicali te Joseph,R.; Sudalai, A.; Ravindranathan. T, Tetrahedron Lett., 1994, 35, 5493
75%
a 1 NH2
0:
x
NH;?
86%
*
Gagnon,J.L.; Zajac Jr.. W.W, Tetrahedron Lett., 1995, 36, 1803
SECTION 173: KETONES FROM ESTERS I/\/yco2Et
Ph
74~
Ph
0
Molander, G.A,; McKie, J.A. J. Org. Chem., 1993, 58, 7216 1. BugnOSnBu3 2. Me1 , LiBr (-CO2) \
Me
3. H+
0
70%
0
Shibata. 1; Nishio, M.; Baba, A.; Matsuda, H. Chem. Lett., 1993, 1953
SECTION 174:
KETONES FROM ETHERS, EPOXIDES AND THIOETHERS 0..
0-. “\A
SiOTx;elCIIflr ph* 0 Fbo, T.B.; Pao. J.M,Synth. C’ommuk, 1993, 23, 1527
Ph
“%
OTBDMS
+ C$I &HzSePh
Ph
’
aq. MeCN , hv
0
1,4-dicyanonaphthalene Ph Pandey. G,; Sochanchingwung, R. J. Chem. Sot. Chem. Commun., 1994, 1945
70%
194
Compendiumof Organic Synthetic Methods, Vol. 9
Section 174
Shono. T,; Yamamoto, Y.; Takigawa, K.; Maekawa, H.; Ishifune, M.; Kashimura. L Chem. L&t,, 1994, 1045
5% Pd(OAc)2, 15% PPh3 PhH , reflux ** can also generatealdehydes 92 RJ, 1. Org. Chem., 1994, 59, 7195
Kulasegaram,S.; m. Bu
.. MABR , CH2C12,-2OOC loo) 73% (0 . 15) 62% SbF3, PhH ,25OC (85 Maruoka, K.; Murase, N.; Bureau, R.; Ooi, T.; &mamoto. I-L Tekzhedron, 1994, 50, 3663 Bu9nI-I , AIBN, PhH reflux ,18h *phAo~
+
ph\
-
32%
50% Crich. D,; Yao, Q. J. Chem. Sot. Chem. Commun., 1993, 1265
MeJFeLi2 , ether , -78OC 45 min
c7Hu0
81% Kauffmann. T,; Neiteler, C.; Neiteler, G. Chem. Ber., 1994, 127, 659 OBz
0 BF3*OEt2 , CH2C12, 0°C
d
ss ss c
OBz
**
84% Fujioka, H.; Kitagaki, S.; Imai, R.; Kondo, M.; Okamoto, S.; Yoshida, Y .; Akai, S.; Kita. Y, Tetrahedron Lett., 1995, 36, 3219
195
Ketones from Halides
Section 175
KETONES FROM HALIDES AND SULFONATES
SECTION 175: Br
1. t-BuLi , THF , -78OC 2.
-78OC + rt Selnick. HG,; Bourgeois, M.L.; Butcher, J.W.; Radzilowski, E.M. Tetrahedron Lett., 1993, 34, 2043 PhB(OH);! , CO, 8O”C, 5h 3% PdClz(MeCN)z
-(=)-No2
3 eq. K2CO3 , anisole 89%
Ishiyama, T.; Kizaki, H.; Miyaura, N.; Suzuki, A. Tetrahedron Lett., 1993, 34, 7595 1. Zn/Ag-graphite , THF ,25OC Ncm(G)w1
2. benzoyl chloride
*
NCp
Furstner. A,; Singer, R.; Knochel. P, Tetrahedron Lett., 1994, 35, 1047
1. Riecke zinc , THF , reflux ,2.5h 2. PhCOCl , CuCN , LiBr Hanson, M.V.; Brown, J.D.; Rieke. R.D.; Niu, Q.J. Tetrahedron Lett., 1994, 35, 7205 0 1. MeLi , LiBr , ClCH21, -78OC + 20°C w (OC)SM Me A 2. H20, 20°C Ph Ph 80% M = MO 86% = Cr Barluenga.; Bemad Jr., P.L.; Con&lb, J.M. Tetrahedron Lett., 1994, 35, 9471
4
OMe
wh3\/\I
Devasagayaraj, A.; m-1.
1.Zn,THF,40°C zc W-h 2. CoBr2, CO, THF , NMP 25OC, 8h P, Tetrahedron Lett., 1995, 36, 8411
1%
Compendiumof Organic Synthetic Methods, Vol. 9
120°C ,20h Satoh, T.; Itaya, T.; Okuro, K.; WM.;
Section 176
0 6ov Nomura, M. J. Org. Chem., 1995, & 7267
OEt
1.
, BuLi OTBDMS
*
THF ,-78°C 2. aq. HF , MeCN 88x99% Hosoya, T.; Hasegawa,T.; Kuriyama, Y.; Matsumoto, T.; hzuki. K. Synlett, 1995, 177 Br Ph . . m.
2 eq. DMSO , microwave
Ph
Br D,; Hammadi, M. Synth. Commun., 1995, 25, 3145 RelatedMethods:
Section 177 (Ketonesfrom Ketones). Section55 (Aldehydesfrom Halides).
SECTION 176: KETONES FROM HYDRIDES This section lists examplesof the replacementof hydrogen by ketonic groups, R-H + R(C=O)-R’. For the oxidation of methylenes,R2CH2 + R2C=O, see section 170 (Ketonesfrom Alkyls).
0
1% RuC12(PPh& , PhH * 0’ t-B&OH,rt 10% aq. Na2SO3
~“lZErsion
7% 47% Murahashi. S,; Oda, Y.; Naota, T.; Kuwabara, T. Tetrahedron L&t., 1993, 34, 1299 crO2c12, cc4 Ph-
Ph
0 99%
w
ultrasound
Luzzio. F.A,; Moore, W.J. J. Org. Chem., 1993, 58, 512
Ph
Section 176
Ketones ffrom Hydrides
0
BaRu(0)2(0H)3,
197
0
LiCl , CHg12
69%
AcOH ,23OC , lh
T.-C,; Mak, C.-K. J. Chem. Sot. Chem. Commun., 1993, 766
0 98% Haddad,N.; Huglin, J.A.; MacKay, M.F.; Reum, M.E.; Ryan, J.H.; Turner,
-w&l;
K.A. J. Chem. Sot. Chem. Commun., 1993, 954 0.2 Yb(OTf’)3, MeNO
OMe
2 Ac20, 18h -A.;
Mitamura, S.; I(ob&.
*
)-=)-OMe
S, J. Chem. Sot. Chem. Commun., 1993, 1157
AC@ ,0.2 Sc(OTf-)3
A-J
MeN02, 50°C, 4h
*
>-i=)-OMe 89%
awada. A,; Mitamura, S.; Kobavashi. S,Synlett, 1994, 545
10%N-hydroxyphthalimide
0 w
73% PhCN ,02, 100°C, 20h PhA Ph I&ii. Y,; Nakayama,K.; Takeno, M.; Sakaguchi,S.; Iwahama, T.; Nishiyama, Y. J+ Org. Chem., 1995, 60, 3934 Ph’
‘Ph
Hf(OTf), , Ac20, LiC104---MeNO
Hachiya, I.; Moriwaki, M.; a.
.
95%
S, Tetrahedron Left., 1995, 36,409
Section 177
Compendium of Organic Synthetic Methods, Vol. 9
PhCOCl , toluene , reflux 0.1 [ ReBr(C0)5 ]
Kusama, H.; Narasaka.
91% (11:4:85 0:m:p) Bull. Chem. Sot. Jpn., 1995, 68, 2379
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 enamines or imines from ketones, see Section 356 (Amine-Alkene). 1. CF$O$iMe3, MeCN Me$i-S-SiMe3 , rt
S P
76%
2. aq. NaHC03 Denl’Innocenti. A.; Capperucci, A.; Mordini, A.; Reginato, G.; Rib, Tetrahedron Lett., 1993, 34, 873 0 PhI\
A.; Cerreta, F.
1. PhCN , TiCld-Zn Ph
2.3% HCl
*
Phq
+ ‘;>=c
7% 86% Gao, J.; Hu, M-Y.; Chen, J-x.; Yuan, S.; Chen, W-x Tetrahedron L&t., 1993, 34, 1617
86%
Pa
Lett., 1993, 34, 3951
Section 177
Ketonesfrom Ketones
d
Tick, CH&
199
92%
lIllIIIIIISi(i~)3
-78OC + -2OOC
& Kniilker. H.-J; Graf, R. Tetrahedron Let?., 1993, 34,4765
(5: 1 anti:syn)
98~72%
pandey. G,; Krishna, A.; Girija, K.; Karthikeyan, M. Tetrahedron Let?., 1993, 34,663l 1. LiN(TMS)z A/q/\
:-.:;:,.,
,4h
+ + 95%
Reetz.;
Haning, H. Tetrahedron Let?., 1993, 34, 7395
Cossy. J,; Furet, N. Tetrahedron Let?., 1993, 34, 8107
0
kEi:%ir?-t, 18h ) &J~.I+ 56~~~lohexmo
J&&s. R&; Taylor, S.R. .I. Org. Chem., 1993, 58, 4469
Cahlez. G,; Figadbe, B.; Cl&y, P. Tetrahedron Let?., 1994, 35, 3065
Section 177
Compendiumof Organic Synthetic Methods, Vol. 9
200
,,,,\\\I”’
TMS
4
CF$&Ag
, Me1 -CH2C12,-78OC+ rt
+
4
..
(6 1 P, Tetrahedron Lett., 1994; 35, 367
Angers, P.; we.
rc 1)
Chen, L.; Gill, G.B.; Pattenden.G, Tetrahedron Lett., 1994, 35, 2593 1. MeLi 2. MnC12 Ph
3. PhCH2Br ; Chau, K.; Cl&y, P. Tetrahedron Lett., 1994, 35, 3069 0 0
BuA
MeCHN2 , Me3Al ,O”C CH2C12, lh
Bu
Maruoka, K.; Conception, A.B.; -to.
/I & #
*
55%
Me I& J. Org. Chem., 1994, 59,4725
2.5 eq. BuySnH , AIBN *
Cl
0T
Bu Bu K,
8h slow addition
q 0 Dowd. PJ Zhang, W.; Mahmood, K. Tetrahedron Lett., 1994, 35, 5563
57%
0
78%
201
Ketonesfrom Ketones
Section 177
SC-1 , Ni2B , H2 (1 atm) 0
*o=O
+
Q-OH
(>99
: B, Tetrahedron Lett., 1994, 35, 5595
BeIisle, C.M.; Young, Y.M.; S
SiMe3
Ph
Ph
Ph
1) >99%
Ph
0
Yb,THF,40°C,2h
-
CHPh;!
‘r(
Ph
Ph
+
OH 68% 29% Taninuchi. Y,; Nagafuji, A.; Makioka, Y.; Takaki. K.: Fujiwara. Y, Tetrahedron Lett., 1994, 35, 6897 0
&
hv’NEt3
t
0
&
48%
Kirschberg, T.; Mat@y. J, Tetrahedron Lett., 1994, 35, 7217 Ph Rh2(O$R*)4, CHgl2, -2OOC,2h 0 Ph
N2
64%
(77% ee , S) Watanabe,N.; Ohtake, Y.; &phimoto. S,; Shiro, M.; Ikegami, S. Tetrahedron L&t., 1995, 36, 1491
Ph
Ph
CHO
Ph *
S 2277
Ph
84%
cat. TMSOTf , rt , CH#2,5h 0 SE; Awachat, M.M.; Kelkar, S.V. Tetrahedron L&t., 1995, 36,
Section 179
Compendium of Organic Synthetic Methods, Vol. 9
202
0
C&12, SmI2, TI-F ,5h
61% -s.;
Tsuchimoto, T. Tetrahedron Lett., 1995, 36, 5937 Bu$nCl - NaBH3CN, AIBN SO;?Ph
t-BuOH , heat
86% Giovannini, R.; Petrini. M,Synlett, 1995, 973 REVIEW: “Organotin Enolates in Organic Synthesis. A Review,” Shibata. I,; Baba, A. Org. Prep. Proceed. Int., 1994, 26, 123 Related Methods: Section 49 (Aldehydes from Aldehydes).
SECTION 178: KETONES FROM NITRILES NO ADDITIONAL
EXAMPLES
SECTION 179: KETONES FROM ALKENES
k
1,4-dimethoxybenzene(sensitizer) hv , MeCN , 12h, rt
Ph B.
0 -
> Ph
90% conversion b-p-d
IJ.T,; Sridhar, M. Tetrahedron Lett., 1993, 34,434l
I \ + (x S
GTign.;
I
TlOAc , CO, MeCN 80°C, 16h 10% [Pd(OAch/2 PPh3]
I \ L s
-
75% Khalil, H.; Levett, P.; Virica, J.; Sridharan, V. Tetrahedron Lett., 1994, 3.5, 3197
Section 179
Ketones from Alkenes
203
10% Pd(OAc), ,20% PPh3 Et4NC1 , CO
88% Gring.;
Redpath, J.; Sridharan, V.; Wilson, D. Tetrahedron L&t., 1994, 35, 4429 1. Et2BHaSMe2 , ether, 25OC 2. Et$n , neat, O°C
Ph 3. CuCN.2 LiCl , THF , O°C 4. PhCOCl d Langer, F.; Devasagayaraj, A.; Chavant, P.-Y.; mochel. P, Synlett, 1994, 410
84%
Me3SiN3, CH2C12,CrQ 59% Reddy, M.V.R.; Kumareswaran, R.; m.
Y.D. Tetrahedron L&t., 1995, 36, 6751
1. [CK12*THF/PhEt2N:BH3, ClOH2w/
PhH , CO]
: ;5:r36h . 9 4. H202, NaOH , NaOt-Bu
C~H2JLH. 70%
Rao, M.L.N.; Periasamv. M, Tetrahedron Lett., 1995, 36, 9069
0 A
9 w=ma *
2 PPh3, DCE d (>20 Lautens. MJ Edwards, L.G.; Tam, W.; Lough, A.J. J. Am. Chem. &..
d 1) 99% 1995, 117, 10276
204
Compendium of Organic Synthetic Methods, Vol. 9
Section 180
1. Cl$=C=O 2. Bu$nH , AIBN 85% (84:16) Dowd. P,; Zhang, W.; Geib, S.J. Tetrahedron, 1995, 51, 3435 See also:
Section 134 (Ethers from Alkenes). Section 174 (Ketones from Ethers).
SECTION 180:
KETONES FROM MISCELLANEOUS COMPOUNDS
Conjugate reductions and reductive alkylations of enones are listed in Section 74 (Alkyls from AIkenes). Ph
>
5) 0
9m
Ph
9 C&Cl2
0 20°C , 30 min 92%
TFP= l,l,l-trifluoropropane Ahamura, A.; Curci, R,; Edwards, J.O. .I. Org. Chem., 1993, 58, 7289
#-(-)=NoH ooc,loi?~ * -(-)=o acetone ,
80% Olah. G.A,; Liao, Q.; Lee, C.-S.; Prakash, GKSJynlett, Ph
O3 , CH2C12, -2OC ,2h
1993, 427
Ph
N-OH * > Ph Yang. Y.; Li, T.; Li, Y. Synth. Commun., 1993, 23, 1121 N---NHTs
PhI(OA&
> Ph
0
95%
, MeCN , rt , 10 min w
Ph
Ph Me
Me 87% Zeng, H.; Chen. Z-C, Sytih. Commun., 1993, 23, 2497
Section 180
J
Ketonesfrom Misc.
205
TS-1, H202, MeOH, 4h
-NHTS
84%
TS-1 = titanium silicate molecular sieves Kumar, P.; Hegde, V.R.; Pandey,B.; Ravindranathan. T, J. Chem. Sot. Chem. Commun., 1993, 1553 Ph
Ph
KMn04, aq. MeCN , rt , lh N-OH
0 *
95%
k=
Wali, A.; Ganeshpure,P.A.; Satish. S&11. Chem. Sot. Jpn., 1993, 66, 1847 NO2
NflHdH202
K2CO3, MeOH Ballini. R,; Bosica, G. Synthesis, 1994, 723 NNHcoNH2
hJ-
PhI(OAc);?, aq. MeCN
0 w
80%
P Me Chen, D.W.; Chen, ZC, Synthesis, 1994, 777
N-NMe2
Me
@uqN)2Sz& 7DCE reflux , lh
Choi, H.C.; m.
&Synth.
N-OH P +
Commun., 1994, 24, 2307
Bentoni te/AgzC03 , PhH
0 t
50%
Ph *
reflux ,4h Me Me Sanabria, R.; Miranda. R,; Lara, V.; Delgado, F. Synth. Commun., 1994, 24, 2805
d=
N-NHTs
(Bu4N)2S208, DCE , reflux 0
lh =c
95%
0
Chen F,; Yang, J.; Zhang, H.; Guan, C.; Wan, J. Synth. Commun., 1995, 25, 3163 REVIEW:
“Macrocycle Synthesis:Cyclic Ketones,Ketoalkenes,Diketones and Dienes of Ring Size C21 Dang, Y. Org. Prep. Proceed. In?., 1993, 25, 309 to &jr” EQ-;
Section 180A
Compendium of Organic Synthetic Methods, Vol. 9
206
SECTION
180A: PROTECTION
OF KETONES
[Rh(MeCN)3(~phos)l Wfh
I7
acetone, rt ,4h
*
PhJL
90%
Me
\ / 9 * 00 o= .M, Tetrahedron Lett., 1993, 34, 8071 HS
SH
n ,-c
S
3m12
0
rt
S
92%
m
Y J Yu, Y.; Lin, R. Org. Prep. Proceed. Int., 1993, 25, 365
p-TsOH , PhH , reflux , cat. TMSI
9
DDQ 9H20 C&C12 95% McDon;tld. CL; Nice, L.E.; Kennedy, K.E. Tetrahedron Lett., 1994, 35, 57 MesSid\/\
0
SiMq OS iMe
CF$O$iMe3 , CH2C12 -78OC
o=
(--bti3
4
LiBF4, MeCN , heat 96% Lillie, B.M.; Avery, M.A. Tetrahedron Lett., 1994, 35, 969 AcCl ,2% SmC13 , rt * 15 min Wu. S.-H.; Ding, Z.B. Synth. Commun., 1994, 24, 2173
Section BOA
Protection of Ketones
207
cat. Pd(OAc)z ,2 NaOAc ,02 )
OSiMe3
58%
0
DMSO
o= Larock. R.c, Hightower, T.R.; Kraus, GA.; Hahn, I?; Zheng, D Tetrahedron Lett., 1995, 36, 2423
S
S
Se02 , AcOH , rt ,25 min
0 .
98%
aldehydes can also be used Phx outounian. S.A, Synthesis, 1995, 39
CuSO4/SiO2, CHC13 20°C ,2d
Caballero, GM.; Gras. E.G,Synth. Commun., 1995, 25, 395
Kurihara, M.; Miyata, N. Chem. L&t., 1995, 263
See Section 362 (Ester-Alkene) for the formation of enol esters and Section 367 (Ether-Alkenes) for the formation of enol ethers. Many of the methods in Section 6OA (Protection of Aldehydes) are also applicable to ketones.
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
208
Compendium
CHAPTER
13
PREPARATION
SECTION
OF
181: NITRILES
FROM
NITRILES
ALKYNES
NO ADDITIONAL
SECTION
182: NITRILES
FROM
183: NITRILES H
A
W-h
FROM
MezC(CN)OH
EXAMPLES
ACID DERIVATIVES
NO ADDITIONAL
SECTION
EXAMPLES
ALCOHOLS
AND THIOLS CN
, MeCN , DEAD
58%
/ C6Hl
Me
. ilk. EL& Synth. Commun.,1993, 23, 2481
SECTION
184: NITRILES
FROM
WCHO
MeOH, rt
* 2. “crude” , MeOH , O°C 2.4 MMPP6 Hz0
aCN 88%
MMPP = magnesium monoperoxyphthalate R.; Gasch, C.; Lassafwm J-K; Llera, J-M.; Wzquez, TetrahedronLett., 1993,34, 141
Ferbdez,
185:
NITRILES ARYLS
Me
ALDEHYDES
1. Me$WI-I2,
SECTION
Section 185
of Organic Synthetic Methods, Vol. 9
FROM
NO ADDITIONAL
ALKYLS, EXAMPLES
J.
METHYLENES
AND
Section 190
SECTION
Nitriles from Halides
186: NITRILES
FROM
AMIDES
Ph
2 PPh3, 2 cc14 Ph
e
209
97% CN H other reagents are also given that lead to this conversion Waers. M.A.; Hoem, A.B.; Arcand, H.R.; Hegeman, A.D.; McDonough, C.S. Tetrahedron Lett., 1993,34, 1453 0
PhA
*
3 NEt3
Ag20, Et1, PhH,25OC
Sznaidman,M.L.; Crasto,C.; Hecht, SM. Tetrahedron
/\I(
NH2
0
Correia.J, Synthesis,
SECTION
Ph-CN
(dark), MS 4A, 12h
NH2
Bu
y-
1994,
Lett., 1993,34, 1581
NaOCl, NaBr, PhWH20 w TBAHS04, Na$?Oe12H@ 1127
187: NITRILES
FROM
82%
Bu-C-N
=
55%
AMINES
NO ADDITIONAL EXAMPLES
SECTION
188: NITRILES
ph-OAc
FROM
ESTERS
Me$iCN,
WPPh& *
THF , reflux ,16h
PhMCN 98% (E.-Z, >9:1)
Tsuji. Y,; Yamada,N.; Tanaka,S. J. Org. Chem., 1993, 58, 16
SECTION
189:
NITRILES FROM THIOETHERS
ETHERS,
EPOXIDES
AND
NO ADDITIONAL EXAMPLES
SECTION
190: NITRILES
I
FROM
HALIDES
AND SULFONATES
1. BuLi, THF, -1OOOC 2.ZnI2 , -loo”c + o”c 3. TosCN, -78OC+ rt ,3h
CN -
Klement,I.; Lennick,K.; Tucker,C.E.; Knochel,P, Tetrahedron
0
84%
Lett., 1993, 34,4623
210
Compendium of Organic Synthetic Methods, Vol. 9
MezC(CN)OH , MeCN , TMG *
MBr
MCN
TMG= 1,1,3,3-tetramethylguanidine Dowd. P,; Wilk, B.K.; Wlostowski, M. Synth. Commun., 1993, 23, 2323 TiC4,
9-
PhgH-CN 93%
Ziener. HE,; Wo, S. .I. Org. Chem., 1994, 59, 3838
191: NITRILES
FROM
HYDRIDES
NO ADDITIONAL
SECTION
192: NITRILES
71%
TMSCN , CH2C12 , O°C
PhgHCl
SECTION
Section 194
FROM
EXAMPLES
KETONES
1. secBuLi, TMSCl 2. secBuLi1
CN
0
ck= t-Bu
89%
3. Me1 4. NaOMe
alsoworkswith aldehydesubstrates Santiago,B.; u.
A.& Tetrahedron
A 0
Ph
Lett., 1993, 34, 5839
1.Me(Cl)AlNH;! * CF3
Kende.AS,; Liu, K. Tetrahedron Lett., 1995, 36, 4035
SECTION
193: NITRILES
FROM
NITRILES
Conjugatereductionsand Michael alkylations of alkene nitriles are foundin Section74D (Alkyls from Alkenes). NO ADDITIONAL
SECTION
194: NITRILES
Ph----CN
2. t-BuOK
FROM
EXAMPLES
ALKENES
NO ADDITIONAL
EXAMPLES
85%
Section 195
SECTION
Nitriles from Misc.
195:
NITRILES FROM COMPOUNDS
211
MISCELLANEOUS
83%
Dandgar.B.P%;Jagtap,S.R.; Ghodeshwar, S.B.; Wadgaonkar,P.P.Synth.Common., 1995,25, 2993
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
212
Compendium of Organic Synthetic Methods, Vol. 9
CHAPTER
14
PREPARATION
SECTION
Section 196
196: ALKENES
OF
FROM
Ph-C=r-Ph
ALKENES
ALKYNES
, DMF , 120°C
10%Pd(OAc)z,20% PPh3 2 TlOAc ,36h Griw Q, Kennewell,P.; Teasdale,A.; Sridharan,V. Tetrahedron Let?., 1993, 34, 153
xz OTs
w;
.
(PhMe$i)$uCNLi2 THF , -78OC -3 rt
de Marigorta,E.M. Tetrahedron Let?., 1993, 34, 1201 1. *&
C3H-W7
vrt
C3H7
$7
Cp2Zr(CH2=CH2). Id
* -c, 68% 2. H+ . Takahashl,T,; Kondakov,D.Y.; Suzuki,N. Tetrahedron Let?., 1993, 34, 6571
(Me$i)$iH , hv (sunlamp) 2h, hexane 70%
Pattenden.G,; Schulz,D.J. Tetrahedron
Let?., 1993, 34, 6787
Section 196
Alkenes from Alkynes
I \
NO2
+
0
I
10% Pd(OAc)z 20% PPh3 , DMF TI(OAc) , 130°C 18h
I b Et&C
‘C02Et Sridharan, V. Tetrahedron
Brown, S.; Clarkson, S.; Grign.;
Le ‘tt., 1993,
34,
157
1.Cp$r(H)Cl , CHg12 20°C ,20 min w 2.5% AgC14
10min TBDMSO Wiof. P,; Xu, W. .I. Org. Chem., 1993, Ph
/-\
0 0 58,
825
TBDMSd
92%
/
1. t-BuLi , pentane/ether 2. -78OC + rt + -78OC )
I
0
<
3. D20 Bailev. WF,; Ovaska,T.V. J. Am. Chem. Sot.,
“u$F
D 88%
115, 3080
1993,
1. PhSCu, ether, BuLi , -35OC 2. addalkynevia syringepump
Nantz. M.H.; Bender,D.M.; Janaki,S. Synthesis, 1993, 577 I
,9(CH’)’
f-
. -
.
1.5;
9
rtanefether ’ -7rc
8 V, WE;
Ph
Ovaska,T.V. Chem. Lett., 1993, 819
85%
214
Compendium of Organic Synthetic Methods, Vol. 9
Et
=
Et
Section 196
1. CHz=CH;! , Cp2ZrBu2 rt, lh
2. H+ Takahashi. T,; Xi, 2.; Rousset, C.J.; Suzuki, N. Chem. Lett., 1993, 1001
Et
91%
HC02H, NEt3,3h
Ph-Et
-
cat.Pdz(dba)3-PBu3
phwEt 89% cis + 5% trans
Tani, K.; Ono, N.; Okamoto,S.; Sate. F, J. Chem. Sot. Chem. Commun., 1993, 386 CO, EtOH , PdC12(PP&,PhH Me3Si
-
siMe3
1 +
5 SnC12,90°C, 1.5h
EQC akeuchi.R,; Sugiura,M. J. Chem. Sot., Perkin Trans. l., 1993, 1031 1.3 eq AlMe ,0.2 Cp$rCI2 Bu 1.5eq.H20 , CHg12 , -7OOC
Bum
77% Bu +
\
2.3M HCl ..
(97 Winf. PJ Lim, S.Angew. Chem. Int. Ed. En@., 1993, 32, 1068
3) quant.
Ph&H , BEt3, PhH -----G&7
42% (12:l 2.3) Miura, K.; Oshima.K.: Utimoto. K, Bull. Chem. Sot. Jpn., 1993, 66, 2356
i=l
C3H-w47
C3H7 Pd(PPh3)4,AcOH , 16h Kini, A.D.; Nadkami,D.V.; Fry. J.L, Tetrahedron Lett., 1994, 35, 1507
w7
97%
CrC12, cat. NiC12 DMF ,25OC, 18h a.
D.M; Wells,C. Tetrahedron
L&t., 1994, 35, 1601
52%
Section 196
Alkenes from Alkynes
215
1. CpzZr(H)Cl , THF , rt PhS(H2C)3
3
*
w
PhS(H2C)3
2.H20
85%
B&; Lindsley, C.; Bhandari,A. Tetrahedron Lett., 0
1994,
0
0
..
(77
Cruciani,P.; Aubert, C.; Malacria.M, Tetrahedron L&t.,
H
=
SPh
Creton,I.; s; 6877
1 //
61%
(> 99% z) Lett., 1994,
J.-F, Tetrahedron
hv , 1%CpCo(CO)2, PhH, heat
-
Stammler,R.; Malacria. SiMe3
35, 6677
-Bu-Bu
Brasseur,D.; Jestin,J.-L.; Nom
C02Me
1994,
23) 69% 54% de
1. Bu@Li , ether 2.2 eq. BuLi , -4OOC , Me2S 3. NH3/NH&l
/ Ph
35, 4669
35,
C02Me
b
93%
W Synlett, 1994, 92
1. Cp$rBu2, PMe3 2.35”C , Eto 9
5c Me$i3OEt
Et0
71%(53:47 cis:trans) 3. H30+ . Takahashl.; Kondakov,D.Y.; Suzuki, N. Chem. Lett., 1994,259 Ph
E
NiBr;?-Zn, diphos, H2
* phm g2% sakai. &; Takai, Y.; Mochizuki, H.; Sasaki,K.; Sakakibara,Y. Bull. Chem. Sot. Jpn., 1994, 67, 1984
Compendium of Organic Synthetic Methods, Vol. 9
216
Section 197
QSiEt3
OSiEt3 3% (PCy3)g12Ru=CHCH=CPh2 CHzC12, (0.6 M) ,2X
,8h
P tie Me Kim, S.-H.; Bowden,N.; mbbs. RcfL J. Am. Chem. Sot., 1994, I16, 10801 Me$iI , Me$n , dioxane SiMe3
95%
61%
5% Pd(PPh3)4,25OC,8 h Chatani,N.; Amishiro,N.; Morii, T.; Yamashita,T.; Murd. S,J. Org. Chem., 1995, 60, 1834 OSi(OEt)3 OH-
Me20%CpZTi(PMe&, HSi(OEt)3
-)&
Me 73%
Qowe. WL; Rachita,M.J. J. Am. Chem. Sot., 1995, I1 7, 6787 Br SmI2,THF , DMPU P2
Phd
= 83%
Zhou,2.; Larouche,D.; Bennett.
SECTION
197: ALKENES
Tetrahedron,
FROM
1995, 51, 11623
ACID DERIVATIVES
0.01PdC12(PPh&, PPh3 c6H’-C0
2H
P 250°C, N2
c6H1v
Miller. J.A,; Nelson,J.A.; Byrne, M.P. J. Org. Chem., 1993, 58, 18 M Cl
, Me$i-SiMe3 , toluene
5%Pd(dba)z, 80°C,4h
Obora,Y.; Tsuii. Y,; Kawamura,T. J. Am. Chem. Sot., 1995, 117, 9814
9840
section 199
SECTION
Alkenes from Aldehydes
198: ALKENES OH
FROM
217
ALCOHOLS
AND THIOLS
H-montmorillonite
dioxane c9H19~ + C9H19d (air free) . reflux ,6h 19) 91% (81 Santhi, P.L.; Siddiqui, M.F. Tetrahedron L&t., 19b3, 34, 1185 -
Kantam. OH
OH
1. SOCl;!, NEt3, 0°C rt NMe(OMe) 2.DBU,0°C + ~
Ph
NMe(OMe)
Ph
92%
T ee) (96.98% Bennani,Y.L.; m.
K.B. Tetrahedron Lett., 1993, 34, 2083 Mo(acac)s, dioxane, reflux
c lOH23
C10H23
OH -f
-
* (1
+ c1a2Y . 1) 92%
Prasad,A.D.; Santhi,P.L. Synth. Commun., 1993, 23, 4;
Kantam.;
phflp::::::’ wph-/c+ ,,/orr
Dorta, R.L.; SE.;
SECTION
73%
8%
Betancor,C. Tetrahedron Lett., 1994, 35, 5035
199: ALKENES
FROM
ALDEHYDES
Me 1.2 LDA Et0 2. PhCHO (>98:2 , E:z)
Coutrot.Ph,; Grison,C.; Gkardin-Charbonnier, C.; Lecouvery,M. Tetrahedron 2767
Lett., 1993, 34,
Compendium of Organic Synthetic Methods, Vol. 9
Section 199
MezCHzPPh3+ BrBuLi , THF , -78OC Ph
SiMes-Bu [94:6 E.-Z (>98%ee, R)]
Bhushan,V.; Lohray, B.B.; En&.
D, Tetrahedron Lett., 1993, 34, 5067
1. H2S, THF , -3OOC 2. NH2NI12 3. -3OOC ,4h C7Hl
seCHO
co1kizo, L .R.; Q&c
a
AC
4. MgS04, -3OOC 5. CaCO3, Pb(OAc)d -c7H-IliI 6. THF , reflux 7. PPh3, THF , reflux Jr.. F& J. Org. Chem., 1993, 58, 43 Cfl l~H0,Zr-t , CrCl3, DMFm
Br
56%(91:9E:Z)
Knecht, M.; Boland.W,Synlett,
1993, 837
CN
CH2(CN)2, CdI2,neat PhCHO heaat,5 min
*
95%
A Ph
CN Prajapati,D.; Sandhu.JS, J. Chem. Sot., Perkin Trans. l., 1993, 739 Bu+CH 2Br2 , 25°C Li , CrCl2, DMFII’HF
Me020CH0
‘,
Me02C/\/\/n/SnBu3 61%
w
D.M; Boulton,L.T.; Maw, G.N. Tetrahedron Lett., 1994, 35, 2231 wCH0
[PPh3=CHMe/I$2NaNTMS23 = *42% (1O:l Z:E)
Chen,J.; Wang,T.; aao. K, Tetrahedron
Lett., 1994, 35, 2827
SiMe3
(Me$i)2CBr2, CrC12 PhCHO &&on.
) DMF ,25”C
D.M,; Comina,P.J. Tetrahedron
84% Ph
Lett., 2994, 35, 9469
SiMe3
Section 200
AIkenes from Alkyls
E10*~-Lpp~3+ Cd-J
219
Br- , dioxane
QH13
13CHO
Ph& , hv , K2CO3, H20, 90°C, 2h
-
YCOEt
70% (78:22 E:Z)
2
(withouthv 12:18 E.-Z) Matikainen,J.K.; Kaltia, S.; Hase.T,SynZett,1994, 817 EtOzC\/sMe3
PhCHO,
DMSO t
EtO&-WPh
cat.CsF, rt + 100°C aed.
93%
M; Ozanne,N. J. Org. Chem., 1995, 60, 6582
SiMe3 PhCHO
t
80%
25OC Ph’+ N-4; Staszewski,J.P.; Fuk, D.-K. Tetrahedron Lett., 1995, 36, 3619
c
C02Et 1. KHMDS , THF, lh 5 eq. lg-crown-5,-78OC 0 w / \P 2. PhCHO I\ Ph PhO OPh Ic Tetrahedron
+ 4 Ph
..
(99 A&I.
EtOg
C02Et
1) 98%
Lett., 1995, 36,4107
C02H
Me3SiCH=C=O,BF3GEt2 PJCHO mk.
-/P
90% (1:l E.-z) T&; Zhang,Y.; Huang,J.; Smith, D.C.; Yates,B.E. Synth. Common., 1995, 25, 15 RelatedMethods:Section207(Alkenesfrom Ketones).
SECTION
ZOO:
ALKENES FROM AND ARYLS
ALKYLS,
METHYLENES
Thissectioncontainsdehydrogenations to formalkenesandunsaturated ketones,estersand amides.It alsoincludestheconversionof aromaticringsto alkenes.Reductionof arylsto dienesis foundin Section377(AIkene-Alkene).Hydrogenation of arylsto a.Ikanes and dehydrogenations to formarylsareincludedin Section74 (Alkyls from Alkenes).
220
Compendium
of Organic Synthetic Methods, Vol. 9
Section 203
CgK , THF
*
Weitz, 1.S.; wov&.
M1 J. Chem. Sot., Perkin Trans. I ., 2993, 117 Br Me0
A
2F
Pseudomonas cepacia AC1 100
OHC
OH
* OMe Artaud, I.; Tomasi, I.; Martin, G.; Petre, D.; Mansuy, D. Tetrahedron
SECTION
201: ALKENES
Related Methods:
FROM
ti:H CHO Lett., 1995, 36, 869
AMIDES
Section 65 (Alkyls from Alkyls). Section 74 (Alkyls from Alkenes). 1. PhLi, THF , 0°C 85%
Jurata, H.; Ekinaka, T.; Kawase, T.; gda, M, Tetrahedron
SECTION
202: ALKENES
Belier. aFischer,
SECTION
H.; Kiihlein,
203: ALKENES
n
FROM
AMINES
K. Tetrahedron
FROM
Lett., 1993, 34, 3445
Lett., 1994, 35, 8773
ESTERS
1% Pdz(dba)3-CHC13 ,2.2 HCOOH 2% chiral phosphine , dioxane 1,8-his-(dimethylamino)naphthalene 20°C ,22h :
%, ++H MeO,CO Me 96% (85% ee, R) . T,; Iwamura, H.; Naito, M.; Matsumoto, Y .; Uozumi, Y .; Miki, M.; Yanagi. J. w. Am. Chem. Sot.., 1994, 116, 775 02
Section 205
SECTION
AIkenes from Halides
204:
ALKENES FROM THIOETHERS
221
ETHERS,
EPOXIDES
Te , THF
OAc
I
OH
LiBHEt3 c Ph Ph DC,; Zhang, Y.; Discord& R.P. J. Org. Chem., 1994, 59, 1004
uenishi. J,; Kubo, Y. Tetrahedron
A
65%
Lett., 1994, 35, 6697
set-BuLi , -78OC+ rt ,90 min 76%
Bu
Bu
Gr
Doris, E.; Deschoux, L.; Mioskowski,
SECTION
AND
205:
ALKENES
C. Tetrahedron
FROM
Bu
Lett., 1994,
HALIDES
Bu 3.5, 7943
AND SULFONATES
Bu$nH , AIBN , Tol, reflux Ph Destabel,C.; Kilbum, J.D. Knight, J. Tetrahedron Lett., 1993, 34, 3151 9
.
nI \
..Li,TI-IF,rt,lh 2. ZnCl;!, THF , O°C-+ rt Br
w , THF ,66OC
m. 1993,
5% “Pd(PPh3)2” , 1Oh T&; Gilbert, A.M.; Huttenloch, M.E.; Min-Min, G.; Brintzinger, 34,
3551
H.H. Tetrahedron Lett.,
Compendium
222
Br
Me$i
of Organic Synthetic Methods, Vol. 9
MeLi,
Section 206
20°C 82%
-A %k siMe3 Br Bu Bu Baird. M.S; Dale, C.M.; AI Dulayym, J.B. J. Chem. Sot., Perkin Trans. I., 1993, 2
c14H16’-\
eq. MezS=CHz
, THF
L,
1373
C14h6
92% -1OOC + It AIcaraz, L.; Hamett, J.J.; Mioskowski, C.; Martel, J.P.; Le Gall, T.; Shin, D.-S.; Falck, J.R. Tetrahedron Lett., 1994, 35, 5453 Br
1. CuCN.2 LiCl , DMPU CSH
-
17Zd
C8H1-
2. E-hexenyl iodide, 60°C ,12h
Bu quant.
Marquais, S.; Cahiez, G.; Knochel. P,Synlett, 1994, 849 Br Ph L WR.;
SmI2,THF,5min
Ph
= i Br Bessho, K.; Yanada, K. Chem. Lett., 1994, 1279
r
I Bu 3SnHPh
*
Phm
/
10% Pd/C , 10% CuI ,20% AsPh3 NMP , 80°C 75 Me0 Me0 Roth, G.P.; Farina, V.; Liebeskind, L.S.; Pena-Cabrera, E. Tetrahedron
C; Aronica, L.A.; Lardicci, L. Tetrahedron
SECTION
206: ALKENES
FROM
Ph
I
82%
Lett., 1995,
EtMgBr , THF , O°C
MaIan=
Ph 95%
36,
quant. Lett., 1995, 36,9189
HYDRIDES
For conversions of methylenes to alkenes (RCH2R’ + 200 (Alkenes from Alkyls). NO ADDITIONAL
EXAMPLES
RR’C=CH2),
see Section
2191
Section 209
223
Alkenes from Alkenes
SECTION
207: ALKENES
FROM
KETONES
65%
PhMe , 50°C
Me
Petasis. N.A; Bzowej, E.I. Tetrahedron
Lett., 1993,
34,
943
(Me0)2POCHgO2Me 0
(-)=yo2t% LiOH , THF , MS , reflux ,4h5c Cardilli, A.; Lattanzi, A.; Orelli, L.R.; Screttri. A, Tetrahedron
wsz; 3383
t-B+(-)=o -a.
$ ~~;;f;;~r2*
t-Bu-(-)=<
S,; Horiuchi,M.; Takai, K.; ytimoto. K, Chem. Lett.,
0II 0
Lett., 1994,
1995,
35,
71% 259
1. EtLi , CeC13 , THF , -78OC 2. KH , DMF , 50°C
P Ph/ I Ph
-1c
*Ph* 95%(92:8E.-Z) Ph . 11.G,; Marcantoni,E.; Sambri,L.; Tamburini,M. Angew. Chem. Int. Ed. En@., 34,2046 RelatedMethods: Section199(AlkenesfromAldehydes). SECTION
208: ALKENES
FROM NITRILES NO ADDITIONAL EXAMPLES
SECTION
209: ALKENES
FROM ALKENES
2% PhH, 20°C Ph Fu, G.C.; Nguyen, S.T.; Grubbs. R,H. J. Am. Chem. Sot., 1993, 11.5, 9856
Ph 84%
1995,
Compendium of OrganicSyntheticMethods,Vol. 9
224
Section209
h\ 9
10%Sc(OTf)3
A/
/
CH2C12,O°C, 13h
I 5c > newDiels-Aldercatalyst Kobwashi. S,; Hachiya,I.; A&i, M.; Ishitani,H. Tetrahedron Lett., 1993, 34, 3755
OTBS
ArN=Mo(OR)=CHRcatalyst
OTBS
PhH, 20°C,30 min 91% Fu, G.C.; Grubbs. R.H,J. Am. Chem.Sot., 1993, 115, 3800 2
Ph-
1%Mo[OC(CF&Me]2(NAr)CHCMe2Ph * pl/%/+c6HD
+
89%
W-h~
Qowe. W.E,; Zhang,Z.J. J. Am. Chem. Sot., 1993, 115, 10998
&
1.PhBr , THF , Pd(PPh& NaOH , reflux , 12h 2. NaOH, Hz02
P -
8,
siM!e3
L&t., 1994, 35, 27 w17
SmI2 PhH/HMPA, rt , 10min
Ph
\aI’ O-l/ ()/\\ w-h7
83%
siMe3
J.&; Colbert,J.C. Tetrahedron
I I J
k
* d
Kunishima,M.; Hi&i, K.; Tani, S,; Kato, A. Tetrahedron
Ph
76%
Lett., 1994, 35, 7253
8%(PCy3)g1,Ru=CHCH=CPh2 PhH ,55”C, 3h
Miller, S.J.; Kim, S.-H.; Chen,Z.-R.; Grubbs.R&J. Am. Chem. Sot., 1995, 117, 2108
Section 210
Alkenes from Misc.
225
(96.
4)
44%
W,; Schrisder, F. Tetrahedron Lett., 1994, 35,7935
B
Ni(dppe)Clz,iPrMgBr , THF Me$iCl , rt , (seconds)
Ma1 _
,; Urso,A.; Lardicci,L. Tetrahedron L&t., 2995, 36, 1133
Ar = 2,4-dibromophenyl 68%(97%ee) ; Calabrese, J.C. J. Am. Chem. Sot., 1995, 117, 8992 REVIEW:
“Reagent-Controlled AsymmetricDiels-AlderReactions,”Qh.T,; Reilly, M. Org. Prep. Proceed. Int., 1994, 26, 129
SECTION
r
210: 0 II 0888q pN \ t-Bu
ALKENES FROM COMPOUNDS
MISCELLANEOUS
1. BuLi , THF , -78OC 2. 4.C EtI1lH23C&Me 3. KOt-Bu
CllH23
-Y 5. CeC13,NaBH4 6. THF, 105OC,20h 63x%x93x92% (102:1 E.-Z) Denmark. S.E,; Amburgey,J. J. Am. Chem. Sot., 1993, 115, 10386
226
Compendium of Organic Synthetic Methods, Vol. 9
2% Pd(acac)z , BuLi , THF , reflux *
Section 210
vGoH21
70%
Gai, Y.; Jin, L.; Jnlia. M.: Verneaux. J.-N, J. Chem. Sot. Chem. Commun., 1993, BuLi
9 2%
1625
Wa~d3
O°C +
reflux
+
C3H7-C3H7 79% (76:24 E.-Z)
Jin, L.; Julia. M.; Verpeaux, J.N. Synlett, 1994, Ph-s-
215
KOH , Al203 , CBr2F+BuOH
Ph
t
Phm
02
Ph
96% (Ihan. T.-L,; Fang, SF.; Li, Y.; Man, T.-O.; Poon, C.-D. J. Chem. Sot. Chem. Commun., 1994, 1771
Ph
02Ph
4
8 eq. SmI2, THF , DMPU 35 min
*
PhwPh
95% Ph Keck. Cr.E,; Savin, K.A.; Weglarz, M.A. J. Org. Chem., 1995, 60, 3194
OEt s6 II
Shimagaki.
.OEt
(E:Z 9:l)
Lawesson’s reagent, xylene *
reflux ,22h
CgH1gwC$117
quant. Lett., 1995, 36 719
0 M,; Fujieda, Y.; Kimura, T.; Makata, T. Tetrahedron Mg” , cat. HgC12, EtOH SO2Ph
5 rt ,2h
Lee, G.H.; Lee, H.K.; Choi, E.B.; Kim, B.T.; Pak, cI.S, Tetrahedron REVIEW: “Rare Earth Metal Trifluoromethanesulfonates as Water-Tolerated Organic Synthesis,” Kobavashi. S, Synlett, 1994, 679
Let?., 1995,
98% 36,
5607
Lewis Acid CatIaysts in
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
Oxides from Alcohols
Section 213
CHAPTER
227
15
PREPARATION
OF OXIDES
This chapter contains reactions which prepare the oxides of nitrogen, sulfur and selenium. Included are N-oxides, nitroso and nitro compounds, nitrile oxides, sulfoxides, selenoxides and sulfones. Oximes are considered to be amines and appear in those sections. Preparation of sulfonic acid derivatives are found in Chapter Two and the preparation of sulfonates in Chapter Ten.
SECTION
211: OXIDES
FROM
ALKYNES
1. ClPPh2 , NEt3 , THF , -78°C
-coMe
; Slattery, B.J. Tetrahedror~~k~.,1994, 35, 5137
SECTION
212: OXIDES
\ 0 I
FROM
ACID DERIVATIVES SnMe3
SO2Cl Me
*
PhCl, 130°C
/
Me
2d
Neumann.W.P,; Wicemec,C. Chem. Ber., 1993, 126, 763
SECTION
213: OXIDES
FROM
ALCOHOLS
>(
0
I , -40°c 0 CH2C12 2. air
AND THIOLS
1. -S-l Gu, D.; m
IIN, Tetrahedron
Lett., 1993, 34, 67
-so$-I
74%
228
Compendium
SECTION
214: OXIDES
of Organic Synthetic Methods, Vo19
FROM
ALDEHYDES
NO ADDITIONAL
SECTION
215:
OXIDES ARYLS
FROM
EXAMPLES
ALKYLS,
NO ADDITIONAL
SECTION
216: OXIDES
FROM
217: OXIDES
Ph-
NI OH
Ph
FROM
METHYLENES
AND
EXAMPLES
AMIDES
NO ADDITIONAL
SECTION
Section 219
EXAMPLES
AMINES
0,05 Pr4N Ru04 , 1.5 NM0
b
Ph*?-
Ph I %
MeCN,rt,2d
75% (>50:1 ZE) Goti. A,; De Sarlo, F.; Romani, M. Tetrahedron
L&t., 1994, 35, 6571
H2N-(=)-co2H ,““” * Webb. K&;
Seneviratne, V. Tetrahedron
Lett., 1995, 36, 2377
SECTION
218: OXIDES
ESTERS
FROM
Na$02Tol, THF 0.01 Pd(PPh3)4, rt i)Ac
chiral phosphine ,72h
S02Tol
..
(10 Eichelmann,
H.; M.
SECTION
219:
H.-J, Tetrahedron
OXIDES FROM THIOETHERS
S
Guertin, K.R.; -de.
L&
OS(=O)Tol 1) 83%
Asymmetry, 1995, 6, 643
ETHERS,
5% TPAP ,3 eq. NM0 MeCN , 30°C, 4A MS ,2h 0
+T
EPOXIDES
w
TPAP = (n-Pr)fl Ru04 Tetrahedron Lett., 1993, 34, 5369
AND
92%
Section 219
Oxides from Ethers
WW4,
229
hv (Pyrex)
7I
PhHsAMe PhHsL
CH2Q
Me
92% Ramkumar, D.; $3.nkararaman. S, Synthesis,
1057 ?I
H202, MeCN , K2C03
PhHS-Me Page. PC&,
1993,
PhHs-
Me 82% MeOH, O°C ,2h Graham, A.E.; Bethell, D.; Park, B.K. Synth. Commun., 1993, 23, 1507 Mn02, Me3SiC1, MeOH
Ph--‘,Me
0 II 99% S ’ Me 23, 1759
w Ph.
Bell&a, F.; Ghelfi. F,; Pagnoni, U.M.; Pinetti, A. Synth. Commun., t-BuOOH, H20, 70°C, 30min BuHS,
*
Bu
1993,
0 II
B/N Bu J+inmelli. F,; Pellegrino,R.; Pizzo, F. Synth. Commun., 1993, 23, 3157
quant.
0
cyclohexanone monooxygenase w
Ph?*
II Ph/‘*
73%(99%ee, R) Secundo,F.; Carrea.G,; Dallavalle,S.; Franzosi,G. Tetrahedron Asymmetry, 1993, 4, 1981 1.35eq.oxone * rt, 1.2h with 0.65eq.Oxone- obtain47%sulfoxide We&J&
Tetrahedron
Lett., 1994, l
‘44
1.1
83%
35, 3457
P
$3F3
.N \ + F
0
II 95% CHC13, CFC13, -40°C ph\/s\ with 2.7 eq.,obtainthe sulfone(91%) DesMarteau.D.D,; Petrov, V.A.; Montanaari,V.; Pregnolato,M.; Resnati.G, J. Org. Chem., 1994, 59, 2762
ph\/s\
C4F9
*
230
Compendium
of Organic Synthetic Methods, Vo19
NaI04, cat. RuC13eH20 Ph-‘-
Ph
Su. W. Tetrahedron
Section 219
0
/
0
NH Ph-S-Ph
lh Lett., 1994, 35, 4955
quant.
NHAc &
mcpba
*
NHAc
xfx
+x)c
C
.
(8 Glass. R&; Singh, W.P.; Hay, B.A. Tetrahedron
1. Ph\/SIMe
I
3)
Lett., 1994, 35, kO9
H202, ether, DBU , -28OC (-)-camphorsulfonylimine 1
2. aq. Na sulfite Me. P.CB,; Heer, .J.P.; Bethell, D.; Collington, 1994, 35, 9629
quant (35% ee, R) E.W.; Andrews, D.M. Tetrahedron Lett.,
NaOCl , TEMPO,
Ph”,
Me
Bu@Cl , CH#X2,
KBr
0 II
* PhHs,
satd. NaHCO3
Me
87% Siedlecka, R.; Skarzewski.
J, Synthesis, 1994, 401 0 II
PhIO , cat. TsOH , MeCN ,25OC *
Ph/‘\Me . . avlca
.
82%
Ph/‘\Me G, Synth. Commun., 1994, 24, 2223 1. Mn02-35% aq. HCl , MeOH 0°C + 10°C, 0.75h
Pl?
0 II
t
Me
99%
2. NaOH Ph/‘lMe Fabretti, A.; Ghelfi, F.; Grandi. R,; Pagnoni, U.M. Synth. Commun., 1994, 24, 2393 NaBQ Ph /‘-Me
, II, wet zeolite F-9
0 w
II
CH2C12, lh PhRSNMe Hirano, M.; Kudo, H.; rvl[orimoto. T, Bull. Chem. Sot. Jpn., 1994, 67, 1492
82%
Section 219
Oxides from Ethers
231
PhIO , MeCN , lh 10% Mn salen catalyst
Ph-‘lMe
0 II ‘-Me
PF
57% (62% ee, R) Noda,K.; Hosoya,N.; Irie, R.; Yamashita,Y.; J(atsuki.T, Tetrahedron, 1994, 50, 9609
p-Tel/
‘+Me
0 II HS-Me p-To1
chiraloxaziridine, CHg12 t o”c
70% ee W .B,; Kochanewyczm,M.J.; Lovely, C.J.; Boyd, D.R. J. Chem. Sot. Chem. Commun., 1994, 25 69
PhMezCOOH, Ti(OiPr)d, Hz0 PhjSIMe
77% (99% ee,R)
II
*
S
(RR)-DET, CH2C12,-2OOC Ph’ ‘Me Brunel,J.-M.; Diter, P.; Duetsch,M.; Kag;ln. HB, J. Org. Chem., 1995, 60, 8086 1.5M HNO3,1% FeBq ,30 min
0 II
*
B+Bu
84%
B/\Bu Sutiez, A.R.; Rossi,L.I.; Martin, S.E. Tetrahedron Lett., 1995, 36, 1201
B4s\
SiO2, CH2C12,t-B&OH > Bu 30min
0
II S Bu’ ‘Bu
86%
with 2 eq. t-B&OH, obtain83%of sulfone P.J, Tetrahedron Lett., 1995, 36, 3825 Breton,G.W.; Fields,J.D.; m. cyclohexanone monooxygenase *
PhAS’
Pasta.P,; Carrea,G.; Holland,H.L.; Dallavalle,S. Tetrahedron
PhHs,
Me
Nagata,T.; -K.;
Ph-S’ II
0 97% (54% ee, R) Asymmetry, 1995, 6, 933
0
02 , m-xylene, Mn (III) salencomplex t
II
66%(51%ee) t-BuCHO, rt Me Yamada,T.; Mukaiyama,T. Butt. Chem. Sot. Jpn., 1995, 68, 3241 Ph”,
232
Compendium of Organic Synthetic Methods, Vol9
SECTION
220: OXIDES
FROM
HALIDES
Section 222
AND SULFONATES
Phi , CuI , DMF , heat PhS02Na Suzuki. H,; Abe, H. Tetrahedron Lett.,
SECTION
221: OXIDES
a 1995,
FROM
36,
PhSO$‘h
6239
HYDRIDES
NO2-03, CH2C12 *
Me -1OOC ,3h
a; M. From
. . .
51%(57:2:41o:m:p) Murashima,T.; Kozai, I.; Mori, T. J. Chem. Sot., Perkin Trans. I., 1993, 1591 It; Mori, T. J. Chem. Sot., Perkin Trans. I., 1995, 29 1 aryl
Suzuki.; From
.
aryl
Suzuki.;
esters:
meta-nitro
is the
major
product
Tomaru,J.-i.; Murashima,T. J. Chem. Sot., Perkin Trans. I., 1994, 2413 acetates:
ortho:para
predominates
(60:40)
Tatsumi,A.; Ishibashi,T.; Mori, T. J. Chem. Sot., Perkin Trans. l., 1995, 339 NO2-03, MeCN, MgO , O°C
R = Et R=H
95% (14:31:55 0:m:p) 0% . &&,l, H; Yonezawa,S.; Mori, T. Bull. Chem. Sot. Jpn., 1995, 68, 1535 REVIEW:
“Ozone-MediatedNitrationof AromaticCompounds with LowerOxidesof Nitrogen,”Mori, T.; &z&i. K Synlett, 1995, 383
SECTION
222: OXIDES
J5 Olah, GA.;
0
FROM
KETONES
1. NH20H, PtCl , KOH NO2
2. CF3C03H
(1113exo:endo) Ramaiah,P.; P&ash. CKS, J. Org. Chem., 1993, 58, 763
60%
Section 225
SECTION
Oxides from Misc.
223: OXIDES
FROM
233
NITRILES
hv (254 nm) SO2Ph Li, C.; Fuchs. P.L Tetrahedron
SECTION
224: OXIDES
55%
MeCN ,25,C, 2h Lett., 1993, 34, 1855
FROM
ALKENES
Et*\ 0-N& EtO’\, 0
9 Bu$nH
toluene, AIBN (syringepump)
mBu
EtO\ -Bu EtO-[, 0
Balczewski,P.; MikoIajczyk, M. Synthesis, 1995, 392
SECTION
225:
OXIDES FROM COMPOUNDS
72%
MISCELLANEOUS
PhMgBr, THF ,25OC
*
71%
i?h Cardellicchio,C.; Fiandanese, V.; Naso.F,; Pietrusiewicz,KM.; WSewski,W. Tetrahedron Lett., 1993, 34, 3135
PhCHO t cDc13
Oe5M
Me2N
t-Bu + Me2N
Denmark.SE,; Griedel,B.D.; Coe,D.M. J. Org. Chem., 1993,*58, 988
t-Bu
234
Compendium of Organic Synthetic Methods, Vo19
PhO#
Ph
7
Section 225
S02Ph 1. LiNAPH
2.
Br-
. . Yu, J.; Cho, H.-S.; Chandrasekhar, S.; Falck. J.R... Mlmkours)sl. (1, Tetrahedron 35,5437
Lett., 1994,
0
0 THF,l-t
Cardellicchio, C.; Fiandanese, V.; mo. Tetrahedron Lett., 1994, 35, 6343
F,; Pacifico, S.; Koprowski,
61% (>98% ee, S) M.; &&u.&wicz. K.M.
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
Section 302
AIkyne - Alcohol
CHAPTER
235
16
PREPARATION COMPOUNDS
OF DIFUNCTIONAL
SECTION 300: ALKYNE - ALKYNE 1. NaNTMS2 ; NBS ~~~‘~~~~-Bu
Maeriotis. P.pL; Vourloumis, D.; Scott, M.E.; Tarli, A. Tetrahedron L&t., 199;, 34, 2071
SECTION 301: ALKYNE - ACID DERIVATIVES NO ADDITIONAL EXAMPLES
SECTION 302: ALKYNE - ALCOHOL, THIOL
vCHO Brown.;
Lo-\ 1. Bu$nI , -85OC+ 2.3 eq. ZnC12
MsO
82%
ether, 25OC, 15 min 2. H202, NaOH Khire, U.R.; Racherla,U.S. Tetrahedron Lett., 1993,34,15 % +9 %
O°C
3.iPqCHO -*
OH
-
Bu 89% (98:2 antisyn)
Katsuhira, T.; Barada. T,; Maejima, K.; Osada,A.; Qku. A, J. Org. Chem., 1993, S&6166
Compendium of Organic Synthetic Methods, Vo19
236
Section 302
.
(94
6) 80% Zhang, L-T.; MO, X-S.; Huang, J-L.; Huang. Y.-Z< Tetrahedro;r Lat., 1993, 34, 1621 00
0, 0
1.2 eq. LDA, THF, -1OOOC 2.2 eq. PhCHO , THJ?
p-To Y
3. NaH ,THF , O°C
I z
H
siAk3
Kusuda, S.; Kawamura, K.; Ueno, Y.; Toru.
0
Ph 83% (>99%ee, S) Tetrahedron Let?., 1993, 34, 6587
1.3 eq. t-BuLi 2. EtCHO , -78OC +
II Ph.
-3OOC *
k Ph Cl Satoh, T.; Hayashi, Y.; Yamakawa.
;>ePh 67%
Bull. Chem. Sot. Jpn., 1993, 66, 1866
1. o-DCB , reflux
w
2. TBAF
Jin, J.; Smith, D.T.; weimb.
SK
J. Org. Chem., 1995, 60, 5366
(PhCd&AlEt2’
Na+
PhCHO To1 , O°C , lh
)
Ph>ePh
OH Ahn, J.H.; Joung, M.J.; Yoon. N.M, J. Org. Chem., 1995, 60, 6173
95%
Bu-Bu C8HlY
I
SmI2, HMPA/PhH
Bu 78% Kunishima, M.; Tanaka, S.; Kono, K.; Hioki, K.; Tani, S, Tetrahedron Let?., 1995, 36, 3707
Alkyne - Amine
Section 305
237
t-BuCHO , Ga13, NEt3 Ph
=
H
-
Pl?
=
TfWfi 80% Han, Y.; Huanae. Y.-7, Tetrahedron L&t., 1995, 36, 7277 Ph
=
SnBu3
+
PhCHO
;>el’h
InC13 , MeCN ,25OC ,30 min 92% Yasu&, M.; Miyai, T.; Shibata, I.; Baba, A,; Nomura, R.; Mats&a, H. Tetrahedron Let?., 1995, 36,9497 PhCHO , Zn , THF
+ satd. NH&l,
Ph>
Phx
rt
.
(89 -I.;
Riazi-Kermani,
F. Synth. Commun., 1995, 2.5,
SECTION 303: ALKYNE SPh
2923
11) 68%
l
- ALDEHYDE 1. s02C12,
cc4, o”c
Fortes. CC;
+ PWCHO 2. CuC12, H@ Garrote, C.F.D. Synth. Commun., 1993, 23, 2869
SECTION
304: ALKYNE
47%
Ph---==----/
- AMIDE NO ADDITIONAL
EXAMPLES
SECTION 305: ALKYNE - AMINE 2 Et2NH2, 1% CuCl
-
(““”
THF , 50°C, 2h Imada, Y.; Yuasa, M.; Nakamura, I.; &&K&K&. F2B
WuJJ.-L;
=
.
NEt2
S.-L J. Org. Chem., 1994, 59, 2282
SiMe3
/
OH
Yan, D.-S.; Tsai, H.-W.; Chen, S.-H. Tetrahedron Let?., 1994, 35, 5003
91%
238
Compendium of Organic Synthetic Methods, Vol9
BuNH2,3%
gBr
Section 307
CuBr , MeCN b
90%
Geri, R.; Polizzi, C.; Lardicci, L.; Qporusso. A.m Gazz. Chim. Ital., 1994, 124, 241
Okita, T.; hobe. M, Tetrahedron, 1995, 51, 3737
SECTION
306: ALKYNE
- ESTER NO ADDITIONAL
SECTION
Phu
307: ALKYNE
- ETHER,
EXAMPLES
EPOXIDE,
THIOETHER
!-c) PhSeSePh L
* Ph- CZC-SePh 75% CuI , HMPA Reckziegel, A.; Menezes, P.H.; Stefani, H.A. Tetrahedron Let?., 1993, 34, 393
=C-Br &;
PhSeBr , CuI , DMF W-4
a
-H
C5H,lpSPh
82% Silveira, C.C.; Reckziegel, A.; Menezes, P.H. Tetrahedron Let?., 1993, 34, 8041
Braga. a;
PhI(OAc)2, PhSeSePh , CH2C12 Ph
w
=
Ph
=
SePh
4o”c 81%
Tingoli, M,; Tiecco, M.; Testaferri, L.; Balducci, R. Synlett, 1993, 211
\ 0I / HO
OCOCF3
, MeCN
DBU , CuC12e2H20 , O°C
0
// 4
83% Godfrev U-D,; Mueller, R.H.; Sedergran, T.C.; Soundararajan, N.; Colandrea, V.J. Tetrahedron Let?., 1994, 35, 6405
Section 311
SECTION
Alkyne - Alkene
308: ALKYNE
239
- HALIDE
k:
1;;
&&velm
V,; Rollin, Y.; G&&henne, C.; Gosmini, C.; P&ichon, J. Tetrahedron L&t.,
1994, 35, 4777
(collidine)$
P-H Brunel, Y.; JXouw. SECTION
PF6
t
Ph
=
I
75%
G, Tetrahedron Lett., 1995, 36, 2619
309: ALKYNE
- KETONE
J-c Cl
‘*
Ph
0
7NW *
2. FVP (5OO*C) ~R.A.;
PlPh
72% x 82%
H&ion, H.; Janosi, A.; Raut, S.V.; Seth, S.; Shannon, I.J.; Smith, F.C.
Tetrahedron Lett., 1993, 34, 5621
SECTION
310: ALKYNE
- NITRILE
1. CuCN , TMSCl , H20 DMSO , MeCN ,72h P-H
t
2. cat. NaI , 50°C uo. F.-T%;Wang, R.-T. Tetrahedron Lett., 1993, 34, 5911
SECTION
311: ALKYNE 2
P-CN
72%
- ALKENE 10% Pd(OAc)2, 30% PPh3 THF , reflux , lh
% &Iandai. T,; Tsujiguchi, Y.; Matsuoka, S. Tetrahedron Lett., 1993, 34, 7615
96%
Compendiumof Organic Synthetic Methods, Vol9
240
Section 311
co Et
SiMe3
2
Pd(dba)z, Ph3As NMepyrrolidone , 40°C
OTf
90%
2, aq. HCl B.H,; Alami, M. Tetrahedron Lett., 1993, 34, 1433
mhutz.
0.05 Pd(PPh)4, 0.1 CuI 2eq.N&,PhH,lh Gueugnot, S.; Linstrumelle, G. Tetrahedron Lett., 1993, 34, 3853
w-h
-
1 5
.
Alaml.;
I
/--OH
c5
11
, Pd(PPh3)4,15min
0
-
M Ferri, F.; m.
*
H
\ 93%
G, Tetrahedron Lett., 1993, 34, 6403
1. norbomadiene, Bu3Sn = Ph 1% PdC12(PPh3)2,80-100°C, 20h Phi 2. heat
Ph
Kosuni. M,; Kimura, T.; Oda, H.; Migita, T. Bull. Chem. Sot. Jpn., 1993, 66, 3522 1. Cfl 11, Pd(PPh3)4, CuI
A
Cl a;
.
Cl
2. PdC12(PhCN)z,piperidine rt
Crousse,B.; Linstrumelle, G. Tetrahedron Lett., 1994, 35, 3543
phtph n. It&;
FVP (500°C)
-
Boeters, C.; Morrison, J.J. J. Chem. Sot., Perkin Trans. l., 1994, 2473
59%
Section 314
Acid - Aldehyde
SiMe3
C
241
Me3Si 1. set-BuLi , THF , -45OC 2.ZnBr2 -45OC + 20°C
SW3
s
3. H30+ SiMe3
-8-
85%
I... Nonnant. J.-F,; Platzer, N. Tetrahedron Lett., 1994, 35, 5645
Meyer, C.; u
Ph Ph 5% HRh(CO)(PPh3)3 35% PEt3 Bu
Z
H+ THF , reflux ,9h 68% (>20: 1 endo:exo)
\
Yamzguchi. M,; Omata, K.; Hirama, M. Tetrahedron Lett., 1994, 35, 5689
Ph
x
SnBu3
, Dibal , THF
YCl
Ni(acac)z , P(OEt)3 yrefiux 77% Cui, D.-M.; Hashimoto, N.; Ikeda. S,; Sato, Y. J. Org. Chem., 1995, 60, 5752
SECTION 312: CARBOXYLIC
ACID - CARBOXYLIC
NO ADDITIONAL
SECTION 313: CARBOXYLIC
ACID
EXAMPLES
ACID - ALCOHOL,
THIOL
1.1:3 TiCldLiAlH4, lh CFC13 , THF , -5°C 2. aq. HCl 62% Garcia, M.; de1 Campo, C.; Sinisterra, J.V.; Llama, E.F, Tetrahedron Lett., 1993, 34, 7973
SECTION 314: CARBOXYLIC
ACID - ALDEHYDE
NO ADDITIONAL
EXAMPLES
242
Compendium of Organic Synthetic Methods, Vol9
SECTION 315: CARBOXYLIC
Section 316
ACID - AMIDE
Me M&J4
44,
1.2.2 LDA , ZnC12 2. HJO+
0/ A 0 T
.
a.
9
*
FY
N w-r
0
H
cog-I 86% (88% de)
U+; Maier, S. J. Chem. Sot. Chem. Commun., 1995, 199 1
5 eq. LDA ,2.5 eq. Al(OiPr)3
0
70% (98% ds/86% ee) J(azmaier. ‘IJ,; Krebs, A. Angew. Chem. Int. Ed. Engl., 1995, 34, 2012
SECTION 316: CARBOXYLIC
0
A?--
ACID - AMINE
1. PhMgBr , THF , -40°C 2. TFA , CH2C12
C02Et
I BoC
3. DDQ , CH2C12 4.10% NaOH , reflux
C02H
-l+’ H
83~72~93% UJ.; Pedregal, C.; Rubio, A.; Valenciano, J.; Navio, J.L.G.; Alvarez-Builla, J.; Vaauero. u Tetrahedron Lett., 1993, 34, 6317
1. Ph//““”
w
OSiMe3
NHPh OSiMq
, ZnBr2, CH2C12 C02H
2. H30+ 84% (35:65 syn:anti)
]Mladenova. M,; Bellassoued, M. Synth. Commun., 1993, 23, 725
Section 318
Acid - Ether
243
Nc /“@Me~~~~h~~~~ep) (02H+ ‘“) (02H derivative, 25OC,40h 2.6N HCl
(94 T, Tetrahedron Lett., 1994, 35, 2713
Soloshonok, V.A.; m.
HO
NH2
Ho
NH2
.
6)
l
CO2H 1, oxaIy1chloride , ether 2. satd.NaHC03, refIux 3. TsNHNH2 , reflux 4. NaE3H4,THF
H
98x39% H
Guan, X.; Borcb=irdt,
Tetrahedron Lett., 1994, 35,3013
*
REVIEWS:
“RecentDevelopmentsin the StereoselectiveSynthesisof a-Amino Acids,” b&&r.
R-Q,
Tetrahedron, 1994,50, 1539
“RecentStereoselectiveSynthetic Approachesto P-Amino Acids,” Cole. IX,
Tetrahedron,
1994,50,9517
Section315 (Carboxylic Acid - Amide). Section344 (Amide - Ester). Section 351 (Amine - Ester).
RelatedMethods:
SECTION 317: CARBOXYLIC
ACID - ESTER
NO ADDITIONAL EXAMPLES
SECTION 318:
CARBOXYLIC THIOETHER
ACID - ETHER, EPOXIDE,
C02H ..
(85 1 0 Mead. K.T; Pi&& SK. Tetrahedron Let?., 1993, 34, 6997
C02H 15)
82%
244
Section 322
Compendiumof Organic Synthetic Methods, Vo19
SECTION 319: CARBOXYLIC OzH
b \
ACID - HALIDE, SULFONATE
1.2.2 eq. see-BuLiKMEDA THF , -9OOC 2.4 eq. c13cc13 , THF , -78OC
3.4N HCl / F Moyroud, J.; Guesnet,J.-L.; Bennetau,B.; Mortier. J I
SECTION 320: CARBOXYLIC
ACID - KETONE 98% (>98% ee)
Na , n-C3H70H, reflux
Moody, H.M.; Kantein. B,; Broxterman,Q.B.; Boesten,W.H.J.; Kamphuis, J. Tetrahedron Lett., 1994, 35, 1777 0.5 C~(ClO4)24 Hz0 02, MeCN ,rt ,lO-15h **OH 0 &sy.
96%
J,; Belotti, D.; Bellosta, V.; Brocca, D. Tetrahedron Lett., 1994, 35, 6089 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
1. CFz=CHLi 2. H30+
NC”
3 H O+ l
3
* *c02H
Tellier. F,; Sauvetre,R. Tetrahedron Lett., 1993, 34, 5433
60% (E)
245
Alcohol - Alcohol
Section 323
0.1 pcy3
,3 TESCI
zs g;*
lbkC~
A/ c3*&,’
c3H--J@902H
Hanamoto, T.; Baba, Y .; Inanaga. J, J. Org. Chem., 1993, 58, 299
=o=’
MnZnBr’ether
;F
Duchsne. A; Abarbi, M.; Pamin, J.-L.; Kitamura, M.;
,!402H Noy~ri,
R. Synlett, 1994, 524
Section 313 (Alcohol - Carboxylic Acids). Section349 (Amide - Alkene). Section 362 (Ester- Alkene). Section 376 (Nitrile - Alkene).
Also via:
SECTION 323: ALCOHOL, THIOL - ALCOHOL,
PhCHO ,SmI2,*
ph%ph
+
THIOL
phhcHo OH 1%
97% in THF + 2.8 eq. HMPA 10% Shiue, J-S.; Lin, C-C.; J%ng. J-M, Tetrahedron Lett., 1993, 34, 335 ~3W~N)6
Bu
9 K2C03
Bu
t-BuOH , H20,12h
r
N 6
~J.A,;
60%
OH 89%
ODHQ
SiMe3
.
80%
) 9 OS04
HOK
SiMe3 (89% ee)
DHQ = dihydroquinidine ODHQ
Rane, A.M.; L6pez, C.J. Tetrahedron Lett., 1993, 34, 1893 AD-mix-P
phoN
-t-BuOH , H20, 0°C PhO&OH 95% Tetrahedron Lett., 1993, 34, 2267 Wang, Z-M.; Zhang, X-L.; SharPless.
246
Section 323
Compendium of Organic Synthetic Methods, Vol9
Me
Me Rh+2 cat. , Cs2CO3 , PhBr
OH Barrett. A.G.w; Itoh, T.; Wallace, E.M. Tetrahedron Mt., 1993, 34, 2233
2 Lebrun, A.; &my.
0
1.2 eq. SmBr2 2. Hz0
J-I,; Kagan.
90% Tetrahedron Lett., 1993, 34, 2311
DHQ-CLB Me3SmC$-i11
H
Me& 93%(71%ee,R) 6H Zargarian, D. Tetrahedron ktt., 1993, 34,
Okatnoto, S.; Tani, K.; &Q. F.: ~K.B.; 2509 1. Ph$iSH , NEt3, MeOH P
2. TBAF, AcOH
-,,i-lt/OH
+
..
(7 Brittain, J.; m.
pASH
1)
Y, Tetrahedron Lett., I993, 34, 3363 H20, 10 KBar , 60°C, Id *
QH E
93% (49% ee) Kotsuki. H,; Kataoka, M.; Nishizawa, H. Tetrahedron Lett., 1993, 34,4037 7
l%Os04,1%catalyst
catalyst = bis-dihydrquinolyl
Crispino, GA.; Jeong, K.-S.-; Kolb, H.C,; Wang, Z-M.; Chem., 1993, 58, 3785
derivative
87%
c
247
Alcohol - Alcohol
Section 323
H
OH
H 1.10% Cp$QCl;! , ether / 2.5 eq. EtMgCl ,25OC, 12h 3. 02,OK
Et
-cc-r
70% (98:2 syn:anti)
Hovevda. A.J&; Morken, J.P. J. Org. Chem., 1993, 58, 4237
,
1%OS04,l-t,3K2c&
OH
Oallyl
3 K3Fe(CN)6,3 MeSO$H2,
t-BuOH-Hz0 82% (39% ee, R) Am. Chem. Sot.,
Morikawa, K.; Park, J.; Andersson, P.G.; Hashiyama, T.; VJ. 1993, 115, 8463 1. Li powder, CH& 5% 4,4’-di-t-Bubiphenyl THF , -4OOC
CHO
H
H
2. H20 +Y
52%
Guijarro, A.; Yus. M, Tetrahedron Lett., 1994, 35, 253
(95
.
5)
93%
Adam. WJ Gevert, 0.; Klug, P. Tetrahedron L&t., 1994, 35, 1681 ’ OH AD-mix f3 , aq. t-BuOH , O°C phw
5r PhS
Ph
Walsh, P.J.; Ho, P.T.; King, S.B.; wss.
+ OH (98% ee, 2S,3R) K.B. Tetrahedron Lett., 1994, 35, 5129
Ph 75%
Section 323
Compendium of Organic Synthetic Methods, Vo19
248
+wph
+
*o/
Jph
955 synmi O (94% ee, syn)
21%
50% ee, S
H Kaneko, Y.; Matsuo, T.; I(,ivooka. S, Tetrahedron Lett., 1994, 35, 4107
Yb-TMS-Br
OTMS
)
fl!p
62%
THF-HMPA TMSO ; Nakahashi, M.; Kuno, T.; Tsuno, M.; Makioka, Y.; I&&i. Tetrahedron Lett., 1994, 35,411l .
.
K.: Fujiwam Y,
0 t-BUSH, hv
)
K
C6H13U
Me
57% (4:l syn:anti) Newcomb. M,; Dhanabalasingam, B. Tetrahedron Lett., 1994, 35, 5193 Ph
0.1 Kz0~04 ,3 MeSOflH2
K3k(cN)6
,3 K2C03
OH
O°C , 12h
R = cinchonidine Corey. EJ.; Noe, M.C.; Grogan, M.J. Tetrahedron Lett., 1994, 35, 6405 NbC13, THF , rt 2 t-BuCHO
t
71% (>95:5 d,l:meso) zvmoniak. J,; Besangon, J.; MoIse, C. Tetrahedron, 1994, 50, 2841
Alcohol - Alcohol
Section 323
Al,KOH,MeOH,rt,5min
+
PhCHO
249
87% (1:l d,l:meso)
Ph Ph
OH Khurana. J.M,; SehgaI, A. J. Chem. Sot. Chem. Commun., 1994, 571 1. dIpczBH , ether , -78OC 2. PhCHO , -78OC *
3. NaOH , Hz02
PhL
= = AH
76% (>95% ee)
Brown. H.C,; Narla, G. .J. Org. Chem., 1995, 60, 4686 P$
*n l
&N,
H
Ph
Ph/
+
Ph e
H
/O
B
Ph
H
* BH3, THF
0
Ph 3 OH (16% meso:RR+SS (99% ee SS)
Quallich. G.J,; Keavey, K.N.; WoodaIl, T.M. Tetrahedron Lett., 1995, 36, 4729 CHO
C
CHO
Bu$nH , PhH ,2O”C hv
ta
OH OH
46% (98: 1 cixtrans)
Hays, D.S.; Fu. G.C, J. Am. Chem. Sot., 1995, 117, 7283 Ph
es 9 t-BuOH , H20, &Fe(CN)e
* Ph K2CO3, (DHQDhPHAL , K~OSO~)OH)~
OH 95% (97% ee , R)
Torii, S.; Liu, P.; Tanaka, H. Chem. Lett., 1995, 319 REVIEWS:
“Synthesis of cr.,@-Alkenediols.A Review,” Patwardhan.S.A, Org. Prep. Proceed. Ink, 1994, 26, 645
Section 325
Compendiumof Organic Synthetic Methods, Vol9
250
“The Oxygenation of Vinyl Cyclopropanesas an Entry Into Stereoselective1,3-Diol Synthesis,” Feldman. Synlett, 1995, 2 17 “Catalytic Asymmetric Dihydroxylation,” Kolb, H.C.; Van Nieuwenhze, M.S.; SharPless. K.B. Chem. Rev., 1994, 94,, 2483
Also via:
Section 327 (Alcohol - Ester).
SECTION 324: ALCOHOL,
Section 357 (Ester - Ester).
THIOL - ALDEHYDE
1. PhCHO , NEt3 *
II-CHO
+)-cO2H
2. H30+ I
51% Barco, A.; Benetti, S.; De Risi, C.; Pollini, G.P.; Spalluto, G.; Zanirato, V. Tetrahedron Lett., zp
34, 3907
1993,
[RhCI(CO)& , 1-methylpyrazoIe HSiMe2Ph , CO (50 atm) Fukumoto, Y.; Chatani, N.; Murai. S, J. Org. Chem., 1993, 58, 4187 0
9vp)c cs /“7\
Ph$=CHOMe , CHCl3,2X
*
CHO
C6H13
Yu, L.; u
C6H13
QH s = = -CHO
77%
ZAJ. Chem. Sot. Chem. Commun., 1993, 232
Section 330 (Alcohol - Ketone).
RelatedMethods:
SECTION 325: ALCOHOL,
mo2
NA Cl
THIOL - AMIDE
1. EtCHO , Li(powder) 3% C1()Hg,THF 2. H20 *
m-92N
w
71% OH
Ram6n, D.J.; Yus. M, Tetrahedron Lett., 1993, 34, 7115 NHTs 3
m.
aq.NaOH, 100°E (-h
.
J,; Bats, J-P.; Hautefaye,P.; Nuhrich, A.; Lamidey, A-M.
Tetrahedron Lett., 1993, 34, 2315
,o~5%
Section 325
Alcohol - Amide
251
H
MeS02NH2, t-BuOH , Hz0 rt , AD-mix-pTM *
mt
Ph
2
96% (96% ee)
v
mt2
OH AD-mix-pm= 5% DHQDz-PHAL (chichona alkaloid-phthalzine reagent),2% K~OSO~(OH)~ Bennani, Y.L.; -less. KB, Tetrahedron Lett., 1993, 34, 2079 COzMe
1. Dibal , -78OC 2.
NHCbz
OTMS
H OMe 3. TiCl2(OiPr)z
.
H
*A
CO&k
= = = I
+
NHCbz
CO2Me
2s
66%
10%
K yooka. S.; Suzuki, K.; Shirouchi, M.; Kaneko, Y.; Tanimori, S. Tetrahedron Lett., 1993, 34, 5;29
HO Me2CuLi , Me (96 Reetz. M.T,; Riilfing, K.; Griebenow, N. Tetrahedron Lett., 1994, j5, 1969
1. BuLi , -78°C 2. LiNaphth , -78°C
pBz
3. PhCHO
me2
FHBz
p +
(1 Foubelo, F.; Yus.
4)
84%
OH
!Ph
..
1) 72%
Tetrahedron Lett., 1994, 35, 4831
1. LDA , THF , -78°C 2. CeC13,THF , rt
* PhnfMe2 3. PhCHO , THF , -78OC 0 OH Shang, X.; Liu. H.-J,Synth. Commun., 1994, 24, 2485
0
68%
. H 3) 66% (97 Taniguchi, M.; Fujii, H.; Oshima. K.: Utimoto, K, Bull. Chem. SO;. Jpn., 1994, 67, 2514
252
Compendiumof Organic Synthetic Methods, Vol9
Section 326
hv
Nfw-b3
-G
c
0 HO
jJ
86%
0 w-h3 Dlttarm., Xu, F.; Qi, H.; Martin, M.W.; Bordner, J.; Decosta,D.L.; Kiplinger, J.; Reiche, P.; Ware, R. Tetrahedron Lett., 1995, 36, 4197 .
.
CL
(CHzO), , acetone, K2CO3 ) ON 0 N 0 N H20, ultrasound I H d OH Jouglet, B.; Oumoch, S.; Rosseau.G, Synth. Commun., 1995, 25, 3869
SECTION 326: ALCOHOL,
B
O@
96%
THIOL - AMINE
1. LDA , TiC12(OiPr)2 THF * 2. t-BuCHO , THF 3. H30+
Et02C&ph
+
Et02Aph
6H
Ph
(>99
OH :
1)
78%
jf
KanemasaI S,; Mori, T.; Wada, E.; Tatsukawa,A. Tetrahedron Lett., 1993, 34,677 OH Ph Ph
2 TsNCO , THF , Id 2% Pd[P(OiPr)&
reflux OH
Xu, D.; -less.
K.B Tetrahedron Lett., 1993, 34, 951
l- WSiMq
, SnC14
CH2C12,O°C,30 min 2.TBAF,m
(1.
.
Hioki. H,; Okauda,M.; Miyagi, W.; It& S. Tetrahedron Lett., 1993, 34, 6131
1.1) 74%
253
Alcohol - Amine
Section 326
Keck. G&, PaIani, A. Tetrahedrdn Lett., 1993, 34, 3223 H
4r H
5 eq. TABH , AcOH/MeCN Me
Me
P
-35OC +
P &
+22”C
* NHOBn TABH = Me+JH BH(OAc)3 Osterhout, M.H.; Reddy, J.P. Tetrahedron Lett., 1993, 34, 3271 N-OBn
DA;
Ph-
Br
2 eq. SmI2, THF-HMPA CHO t N=C , -15OC, 3h
91%
Murakami, M.; Kawano, T.; Ito, H.; Ito. Y, J. Org. Chem., 1993, 58, 1458
0
H 1. LDA 2. PhCHO
+
Ph
*
mn2
Lagu, B.R.; Crane, H.M.; m.
*
NBn2
(80:20, R)
D.C, J. Org. Chem., 1993, 58, 4191 EtzNzCu(CN)Liz , THF
0 -78OC + rt
N. Y,; Asao, N.; Meguro, M.; Tsukuda, N.; Nemoto, H.; Sadayori, N.; Wilson, J.G.; Nakamura, H. .I. Chem. Sot. Chem. Commun., 1993, 1201
254
Compendium of Organic Synthetic Methods, Vo19
Section 326
Yb(OTf)3, NHEt2 CH&
C6H13
97%
,20 min mt2
w-h3
> 99% a-attack Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetruhedrun Lett., 1994, 35,433 C8H
7
Et2NH , LiBF4, MeCN 80°C , 18h
* c8H1ym.YOH Chini, M.; Crotti. P,; Favero, L.; Macchia, F. Tetrahedron Lett., 1994, 35, 761 b
CbZ
0
CbZ
79) 52%
.
(21
&&,Q. T,; Tajiri, IS.; Harimoto, T.; Ninomiya, I.; Kiguchi, T. Tetrahedron Lett., 1994, X5,2205 H
H CH3N02 ,2 eq. AlC13 w 8O”C, 5h
\
/““” 70%
/
.
Sarton,;
Bigi, F.; Maggi, R.; Tomasini, F. Tetrahedron Lett., 1994, 35, 2393 Ph I N /\
1. Li, cat. cl(jf&j 2. PhCHO *
3. H20
Almena, J.; Foubelo, F.; Yus. MJ.
0 o=
68%
PhHN-Ph
various electrophiles were used Org. Chem., 1994, 59, 3210 93% (1:l)
MeCH=N-OMe , iPrOH
sono.
& /
* e’
NHOMe
T,; Kise, N.; Fujimoto, T.; Yamanami, A.; Nomura, R. J. Org. Chem., 1994, 59, 1730
Section 326
Alcohol - Amine
c”, f”’
1. BH#Me2,
255
c’)
THF
J
w
2. MeOH
45%
3. H202, NaOH w-h1
C&9
Goralski. CT%;Hasha,D.L.; Nicholson, L.W.; Zakett, D.; Fisher, G.B.; Singaram. B, Tetrahedron L&t., 1994, 35, 3251 0
A
2
H
Sm , Me$iCl/NaI , MeCN rt, 15min
P
-
9
/
OH
Phq-p 72%
Akane, N.; Hatano, T.; Kusui, H.; Nishiyama, Y .; Ishii. Y cJ. Org. Chem., 1994, 59, 7902
NBn2
mn2
(92:8 RS)
90%
with LDA
(63:7 R:S) 90% Lagu, B.R.; Liotta. DC, Tetrahedron Lett., 1994, 35,4485
l.BMS,THF
J5 ~c.T.;
.
3. H202, NaOH
Hasha,D.L.; Nicholson, L.W.; Sine.
R, Tetrahedron Lett., 1994, 35, 5165
OH ultrasound,Al(Hg) , aq. THF 2h iJo Fitch, R.W.; Luzzio. F.A, Tetrahedron Lett., 1994, 35, 6013
92% NH2
Section 326
Compendiumof Organic Synthetic Methods, Vol9
256
t-BuNH2 , CH2C12 5% Yb(OTf)3, rt ,16h c8H~~mt-Bi8H~~;Bu m
99 P,; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lejt., 1994, 35, 7089 Bn I
Bn I
1. Cp$Zr(Bu);!, THF -78OC+ rt ,4h OMe
2. BF3aEt2, THF , O°C 3. aq. NaOH
82% (>98:2 syn:anti)
Ito, H.; Ikeuchi, Y.; Taeuchi. T,; Hanzawa, Y.; Shiro, M. J. Am. Chem. Sot., 1994, 116, 5469 Na,iPrOH,THF
76% (erythro/threo = 0.8)
Bartoli, G.; Cimarelli, C.; Palmieri. G, J. Chem. Sot., Perkin Trans. I., 1994, 537
A
, SmI2
Q+ \ ‘0I /
*
THP , HMPA
85%
Booth, SE.; Benneche,T.; Undheim. K, Tetrahedron, 1995, 51, 3665 Ph 0
NHPh
PhNH2 , TiC13, PhCHO THF/CH$12, Py , rt *
M-+
Clerici, A.; Clerici, L.; porta 0, Tetrahedron L&t., 1995, 36, 5955
9 % HO Ph
Ph 76%
Section 327
Alcohol - Ester
257
OH
BnNH2,lOkbar ,CH2C12
90% cat. Yb(OTf), , rt ,6d Meguro, M.; Asao, N.; mote.
030s=Nt-Bu , DME ,25OC Phw
Ph
NHBn
Y, J. Chem. Sot., Perkin Trans. I., 1994, 2597
quinuclidine , 36h
NH?-Bu
- Ph+ph
+ Phqph OH
OH
..
(97
3)
Rubinstein, H.; Svendsen,J.S. Acta Chem. Stand. B., 1994, 48, 439 1. TFAA, CHg12 rt ,4h OH
2. K2CO3
95%
Fontenas,C.; Bejan, E.; Haddon, H.A.; Belavoine, G.G.A,Synth. Commun., 1995,25, 629
SECTION 327: ALCOHOL, OBn = =
THIOL - ESTER
t
=
CHO
CO2Me
3% LiC104, -30°C CHg12, 4h
OSiMe2cBu
..
(92 Reetz. M.T,; Fox, D.N.A. Tetrahedron Lett., 1993, 34, 1119
8)
>84%
EtOH , CO, NaBr , iPr2NEt
-I.;
Pd2(C4H7)& , maleic anhydride ‘) H*co2Et Maruyama, T.; Makuta, T.; Yamamoto. A. Tetrahedron Lett., 1993, 34, iI35
w
Me
PhCHO ,5% SmI2,5 min
Ph
CH2C12, -78OC -$< OTMS Van de Weghe, P.; Collin, J, Tetrahedron Lett., 1993, 34, 3881
C02Me OTMS
95%
258
Compendiumof Organic Synthetic Methods, Vol9
/L
OH
Yeast, pet. ether, H20 C02Et
Section 327
*
rt, Id
AC02Et
58% (94%ee) Yeast = Saccharomyces cerevisiae Jayasinghe,L.Y.; Smallridge. A.J,; Trewhella, M.A. Tetrahedron L&t., 1993, 34, 3949 0
0
C02Me Mn(OAc)3@2Hz0
OH
+
A
Cu(OAc)pHzO
9%
78%
25OC
ix
-OH
OMe
Oshima, T.; Sodeoka,M.; Shibasaki,M. Tetrahedron L&t., 1993, 34, 8509 . ;co2Me
NHC02t-Bu
t-Buo2cJ
c
*
-t &Me$‘h w.
‘.~~ao~~;a~ 2.5% aq. HCl
0 i bH
0
J&; Zhang, J. J. Org. Chem., 1993, 58, 294 OSiMe3 I PhCHO
Ph
m12
C02Me
er. LB, .I. Org. Chem., 1993, 58, 2324 TMs
A
OMe
92%
p-MS
10% [Cp2Zr(Ot-Bu)THF][BPh4]
:=
C02Me
PTMS +
&CO$Ie I= Z s=
CH2C12, PhCHO , rt , lh -^(
..
(1.1
1)
95%
Hong, Y .; Norris, D.J.; Collins, S, J. Org. Chem., 1993, 58, 3591 1. LDA 2. Et2AlC1
OH
/\COzt-Bu *
56%
xx 2’ (84:16 syn:anti) m. S&; Fried, J.A.; Grassl, Y.N.; Marolewski, A.E.; Pelton, E.A.; Poel, T.-J.; Rezanka, D.S.; Whittaker, M.R. J. Org. Chem., 1993, 58, 7304 3* ‘s
Section 327
Alcohol - Ester
259
BrCH2C02Et, PhTeLiKeC13 C02Et ether, OOC +
rt 95%
Fukuzawa. S.-i; Hirai, K. J. Chem. Sot., Perkin Trans. I., 1993, 1963 oxido reductase from Geotrichum candidum
C02Et
QH 0 = E
C02Et
500 mM bis-TRIS-HCl 24h , NaDPH , ADH , glucose
93%
(>99% de; 92% ee) Kawai. Y,; Takanobe, K.; Tsujimoto, M.; Ohno, A. Tetrahedron Lett., 1994, 35, 147 PhCHO
+
I-(,, TBSO
~e/wI-MP ()pMp
CH2C12, -78’C
+ OTBS (6
PMP = p-methoxyphenyl
UOPMP &TBS 94) 95% 92%ee
..
Kobayashi. S,; Kawasuji, T. Tetrahedron Lett., 1994, 35, 3329 OH 3 eq. CH2=CHC02Me
COzMe
1.2 MgBr2 , CH2C12 O°C , lh 58% (> 20~1 endo:exo) Woo. SH, Tetrahedron Lett., 1994, 35, 3975 TMS
+
ooka. S,; Kido, Y.; Kaneko, Y. Tetrahedron Lett., 1994, 35, 5243
260
Compendium of Organic Synthetic Methods, Vo19
BnOCH$HO
Section 327
,5% binolTiC12
toluene , O°C ,2h . -K.;
81% (94% ee, R)
.
Matsukawa, S. J. Am. Chem. Sot., 1994, 116, 4077 0
CaMe
MeOH , Amberlyst-15 ,2Oh
96% 0 bd.
OH
* c c R.c; Selvapalam, N. Synth. Commun., 1994, 24, 2743 OHC I
I--
1
CO2iR
L = chiral imine ligand Hayashi, M.; Inoue, T.; C)euni. N, .I. Chem. Sot. Chem. Commun., 1994, 341
o=
Br\/co2Et
, THF ,2h
0
LVT, rt
*
(-pco2Et
LVT = low valent titanium 67% Aoyagi, Y.; Tanaka, W.; Ohta. A, J. Chem. Sot. Chem. Commun., 1994, 1225 1. BuLi , ether, -4OOC 2. PhCHO
2”
H w
P
3.03 , CH2C12, -78°C 4. Me$
Ph*CO
2 Me
51% Hormuth, S.; &i&&
H.-U.; Dorsch, D. Liebigs Ann. Chem., 1994, 121 RuBr&hiral
C02Me
mM.J.;
bis-phosphine)
60 psi H2 , aq. MeOH
*
OH = = z &COzMe
quant. (99% ee, S) Harper, T.G.P.; Kalberg, C.S. J. Am. Chem. Sot., 1995, 117, 4423
Section 328
Alcohol - Ether
261
0
VO(OAC)~ , PhH , TBHP -
A Ph
o/\/O” 98%
Choudary, B.M.; Reddy, P.N. Synlett, 1995,959 Also via:
Section 313 (Alcohol - Carboxylic Acid).
SECTION 328:
ALCOHOL, THIOL - ETHER, EPOXIDE, THIOETHER
E+Z
. 1) (18 Mandai. T,; Ueda, M.; Kashiwagi, K.; Kawada, M. Tetrahedron Lett.: 1993, 34, 111
0 0
Uozumi, Y.; w.
1. 0.1% [PdC1(rtC3H5)]2 0.2% R-MOP, HSiCl3
H RMOP b 65 x 83%
(g5% ee) T, Tetrahedron Lett., 1993, 34, 2335
1. BH#Me2, Me2S , O°C 2. aq. NaOH , Hz02 3. NaOH
mder.
=3 .
OMe
40°C, 24h 2. KF , KHC03, Hz02
78%
G,&; Bobbitt, K.L.t .I. Am. Chem. Sot., 1993, 11.5, 7517
pm2
Section 328
Compendium of Organic Synthetic Methods, Vol9
262
1. BuCHO , Li(powder) 5% DTBB , THF, O°C 2 H o
EtQc1
l
H Et
*
2
gK
87%
Bu
Guijarro, A.; yuS. n& Tetrahedron Lett., 1993, 34, 3487
‘-“’
cat BF3 OEt2 .
42%
l
Mark& I.E.; Bayston, D.J. Tetrahedron Lett., 1993, 34, 6595
phxph
n
2 eq. BHpSMe2 2 eq. TMSOTf
Bartels, B.; Hunter. R, J. Org. Chem., 1993, 58, 6756
7 PhSH , SiO2
;;;p
+ z&SPh
t
20°C, 20h
Me3Si
CdJ
13
89% Raubo, P.; w
C&
13
14%
a-h3
J, Synlett, 1993, 25 ClCH2SPh , SmI2 t
0
(-KS,,
o=
73% Yamashita, M.; Kitagawa, K.; Ohhara, T.; Iida, Y.; Masumi, A.; Kawasaki, I.; Ohta. S, Chem. Lett., 1993, 653
R
1. PhONa , DMF
A0
)
PhOTOBn
2. HCl-H20 k/
OBn
Cwlsen. P.H.J*; Aase, K. Acta Chem. Stand. B., 1993, 47, 617
OH 81%
Section 328
Alcohol - Ether
263
cat. FeC13, MeOH ,25OC
Ph
OH
0.75h
90%
N,; Salehi, P. Synthesis, 1994, 1152
a
OH eq. eq. CH2C12, 12h , rt -
2. HOONa 1.3
c
Re207 ,9
0
2,6-lutidine
OF
78%
OH
0
Boyce, R.S.; Kennedy, R.M. Tetrahedron Left., 1994, 35, 5133
1. SO(Im)2 OH 2. PhO- Li+
OH
34% OH D, Tetrahedron Lett., 1994, 35, 6279
El Arabi Aouad, M.; El Meslouti, A.; Uzan, R.; mere. OH
OH PhthNSCl , CHC13 , 60°C, 4d
SNPhth
64%
Me0
precursor to o-thioquinones Capozzi, G.; Menichetti. S,: Nativi. C,; Simonti, M.C. Tetrahedron Lett., 1994, 35, 9451
v H
Marson.;
HgO , dil. H2SO4 , 20°C Wll
0
Wll
-*
OH 73% Harper, S.; Wrigglesworth, R. J. Chem. Sot. Chem. Commun., 1994, 1879
1. t-BuLi , THF , -78OC 2. cyclohexanone ~T,.A,;
-
*
S
HO Dullweber, U.; Branan, B.M. Heterocycles, 1994, 37, 187
75%
264
Compendiumof Organic Synthetic Methods, Vo19
1. Bu$nCH(OEt)z, BuLi THF , -78OC
PhCHO
Section 328
Ph
CH(OEt)z
c
I
2. aq. NH4Cl
OH 65% Parrain, J.-L.; Beaudet,I.; Cintrat, J.-C.; Duch$ne, A.; Quintard. J.-P,Bull. Sot. Chim. FL, 1994, 131, 304
(CFcO2)Re03 , O°C 2,6-lutidine , CH2C12
McDonald. FL; Towne, T.B. J. Org. Chem., 1995, 60, 5750
-OH
PhSeCl , CHCl3 -
LO,
= = XePh
W Cooper, M.A.; Ward. A.D, Tetrahedron Let?., 1995, 36, 2327
+
L,, ..
= = bH 36) quant.
OH OH
88%
2.H20
Corey. EL; Palani, A. Tetrahedron Let?., 1995, 36, 3485
S
J&l.
S,; Cho, C.M. Tetrahedron Let?., 1995, 36, 4845
HO
Section 329
(3-I
1
265
Alcohol - Halide
0
1.2% Cp2Ti(O4ClC&& , toluene 1% TBAF , Al2O3,5 PMHS , rt
w-h
0
OH
2.1M NaOH , TI-IF
* u PMHS = polymethylhydrosiloxane 94% (70:1) SLJ. Am. Chem. Sot., 1995, 117, 12641 Verdagauer,X.; Berk, S.C.; md. 0
BF3GEt2, NaBH3CN 6h .
0IOH 87%
.
Stlkrrshna. &, Viswajanani, R. Tetrahedron, 1995, SI, 3339 OMe
e’ , MeOH, aq. MeCN , Bu&IClO4 lh
OH 96%
Safavi. A.: Iranpoor. NJ Fotuhi, L. Bull. Chem. Sot. Jpn., 1995, 68, 259 1 REVIEW:
“Metal-Catalyzed Direct Hydroxy-Epoxidation of Olefins,” Adam. W,; Richter, M.J. Accts. Chem. Res., 1994, 27, 57
SECTION 329: ALCOHOL,
THIOL - HALIDE, SULFONATE
1. LDA. ZnCl2 , THF . -78OC mcl
2. PhCHO
80%
Cl Mallaiah, IS.; Satyanarayana,J.; Ila H,; Junjappa,H. Tetrahedron L&t., 1993, 34, 3145
a; 58,486
.
. 77) 74% (23 Furutani, H.; Ansari, M.H.; Sakai, T.; Utaka, M.; Takeda, A. J. Org. Chem., 1993,
266
Compendiumof Organic Synthetic Methods, Vo19
Section 329
1. DibaI , CHg12, -78OC CF$@Et
83%
2.ZnBr2, BussF CHzCl2, 40°C T,; Hayashi, H.; Yamanaka, H. Tetrahedron Lett., 1993, 34, 5777
. ma.
MgBr2, Bu$IBH4 -
ether/CHglz:
72%
‘-Ph +
.Ph 22% “\Ph Bailey, P.L.; Briggs, A.D.; Jackson,R.F.W.; Pietruszka,J. Tetrahedron Mt., 1993, 34, 6611 Mg(NO& , Bu4NBr ,5h CHC13
OH
Y.-Q, Koo, B.-A.; Ko, J.-A.; Cho, Y.-S. Chem. Lett., 1993, 1907
93%
NaI04, NaHS03
k
Masuda, H.; Takase,K.; Nishio, M.; Hasegawa,A.; Nishiyama, Y.; Ishii. Y, J. Org. Chem., 1994, 59, 5550 Lick , DMF , 70°C , Id
Ph
-,jPhJ/H (35
+Lc1 ..
65)
Nymann, K.; Svendsen,J.S. Acta Chem. Stand. B., 1994, 48, I83 Br
PhCHO
OH CN
9 In
CN
84% (56:44 erythro:threo)
Araki, S.; Yamada, M.; Butsugan. Y, BUZZ.Chem. Sot. Jpn., 1994, 67, 1126
90%
Section 330
Alcohol - Ketone
267
REVIEW:
“Regioselectiveanbd ChemoselectiveSynthesisof Halohydrins by Cleavageof Oxiranes with Metal Halides,” m. C,; Righi, G. Synthesis, 1994, 225 SECTION
330: ALCOHOL,
THIOL
- KETONE
Rawal. VH,; Krishnamurthy, V.; Fabre,A. Tetrahedron Lett., 1993, 34, 2899 M F3
3
P 0
,,
15 min 96% Curci, R.; D’Accolti, L.; Detomaso,A.; Fusco, C.; Takeuchi. K.; Ohga, Y.; Eaton.& Tetrahedron Lett., 1993, 34,4559 TIPS
P
PhCHO , Me& rps
w
p”
88%
WPh Shoda,H.; Nakamura,T.; Tanino, K.; Kuwajima, I Tetrahedron Lett., 1993, 34, 6281
1. Me$i(OTf)Z , NEt3 m &
I
2. PhCHO ; Nishio, K. .I. Org. Chem., 1993, 58, 2647
HO*
78%
(919
syn:anti)
Ph OAc
OAc RuC13,MeCO# MeCN - Hz0 - CH2C12
78%
Murahashl. S.-I,; Saito, T.; Hanaoka,H.; Murakami, Y.; Naota, T.; Kumobayashi, H.; Akutagawa, S. J. Org. Chem., 1993, 58, 2929
Compendium of Organic Synthetic Methods, Vol9
xc
Section 330
H
0 0
’ acetone >96%
o”c
OH
OH (>98% ee , R)
D’Accolti, L.; Detomaso, A.; Fusco, C.; Rosa, A.; Curci. R, J. Org. C&m., 1993, 58, 3600
0 II
1. BuLi , CO, -1lOOC THF/pentane/ether 2. rt , H30+ Hui, R.C.; Wang, W.-L. J. Org. Chem., 1993, 58, 5843
Sevferth.;
H PhCHO ,5% Sc(OTf)3, aq. THF *
Ph Y 83%
,; Hachiya, I.; Ishitani, H.; Araki, M. Synlett, 1993,472
Ph
PhCHO 2%
0
9 CH2C12
*
W&)3
PhU
Ph 84%
Ishihara, K.; Hananki, N.; Yamamoto. HJynlett,
1993, 577
0 PhwcHo
+
HMPA,rt,THF
, SmI
2 *
Ph*
0 83% (83:17 antixyn)
Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Chem. Lett., 1993, 959 -
MeC03H , cat. OsC13
Phv0I-I
Phv
MeCN-H20-CH2Q . Murahashl. S.-L; Naota, T.; Hanaoka, H. Chem. Lett., 1993, 1767
0
62%
269
Alcohol - Ketone
Section 330
PhCHO , A1203 ultrasound, 22h
..
(77 Ranu, Ike,
23) 75%
Chakraborty, R. Tetrahedron, 1993,49, 5333
PhCH2CH0 CHO
)
Phk
+
Ph;
H20, SmI2 OH
?)H
.
(39
61) 64%
Miyoshi, N.; Takeuchi, S.; Ohgo, Y. Chem. Lett., 1993, 2129
1.
==c
PhCHO
Bu
, EtCN , -78OC
20% chid acyloxyborane 2. aq. HCl
*
0
= =
Bu
Pha
81% (85% ee, R) Ishihara, K.; Maruyama, T.; Mouri, M.; Gao, Q.; Furuta, K.; Yamamoto. H, Bull. Chem. SOC. Jpn., 1993, 66, 3483
c
1
1. 2.2 eq. SmI3 , tetrahydropyran 2. propanal 3. H30+
0
-
H
c
0
95%
955
(trans:cis)
J.-L; Colomb, M.; Kagan, H.& Tetrahedron L&t., 1994, 35, 1723
OH
TFA , CDC13 ) 2d
ph 0
Dmhoux.;
Doris.
Tetrahedron Lett., 1994, 35, 2017
270
Compendium of Organic Synthetic Methods, Vol9
a Ph
Section 330
Cl
86%
3 eq. pyridine
C02Me
Araneo, S.; Clerici, A.; Porta. 0, Tetrahedron Lett., 1994, 35, 2213
P hl
OH
p)-(=)-oH
Cl
cat. HZSM-5 DCE , reflux
67%
HZSM-5 = acidic zeolite [SiO$A1203 = 401 Paul, V.; Sudalai, A.; Daniel, T.; Srinivasan.V, Tetrahedron Lett., 1994, 35, 2601 0
1. LDA , THF , -78OC 2. (iPrO)$Cl 3. acetone ,
>
8
II Ph 7
, -78OC
OH 5 1% conversion (88% yield)
4. aq. NH8
a.
W,; Mtiller, M.; Prechtl, F. J. Org. Chem., 1994, 59, 2358 OH
0
PhCHO , 10% Sm(hmds)J -30°C) 18h
Sasai, H.; Arai, S.; Shibasaki. M, J. Org. Chem., 1994,
UI -“iMe
VS.;
.
PhCHO , Yb(OTf)3
OH
aq. THF, rt , 19h
Hachiya, I. J. Org. Chem., 1994, 59, 3590
Ph 9 1% (73:27 syn:anti)
271
Alcohol - Ketone
Section 330
1. Me3A1, PhSeH 2. Me$=CHCH2CHO
92%x62%
w
3. BusnH, hv
I.-Y.C,; Lee, J.H.; Lee, H.W. Tetrahedron Lett., 1994, 35, 4173 OH
0
l.NaHMDS,THF * 2. PhCHO
Ph
Ph
+
.
(94
6)
69%
Goh, J.B.; Lagu, B.R.; Wurster, J.; J,iom. DC, Tetrahedron Lett:, 1994, 35, 6029 H 0
1, LHMDS , toluene-hexane t-Bu
2. Y(OTfl3,
HIIIIII -
OOC, 18h
t-Bu
x,
99% 0 crou. P,; Di Bussolo, V.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett., 1994, 35, 6537 i FfKfR-BINAPI
Ph-
, PhC12SiSiMe3,PhH Ph* w
0
l
3+
4. HBF4 5. H202 Matsumoto, Y.; Hayashi. T,: Ito, Y. Tetrahedron, 1994, SO, 335
OH
0
73~78%
, Yb(OTf-)3, 0°C 0
PhCHO
Ph
iPrmt , ether, 3h
92% (34:66 threo:erythro)
Fukuzawa. S.-i,; Tsuchimoto, T.; Kanai, T.. Bull. Chem. Sot. Jpn., 1994, 67, 2227
Compendiumof Organic Synthetic Methods, Vol9
272
Jr
Ph
Section 330
OTMS OzMe -=c Me
BuflClOd , e’
SnBu3
*
Ph=
Yoshida. L; Morita, Y.; Ishichi, Y.; Ime. S, Tetrahedron Lett., 1994, 35, 5247
dPh
Enbolm.;
Sm1z2Br
94%
f”fPh
Schreier, J.A. J. Org. Chem., 1995, 60, 1110 PhCHO , MS 4A, 13h 5% PdClz[R-DINAPI-AgOTf *
23°C
Phu;
+
Phufi
87%
9%
Sodeoka,M.; Ohrai, IS.; Shibasaki. m J. Org. Chem.,1995, 60, 2648
‘: 0
, acetone, IX, ld 92%
OH 0 Bovicelli. Pa;Lupattelli, P.; Sanetti, A.; Mincione, E. Tetrahedron Lett., 1995, 36, 3031
OHC Zn(NO3)2, acetoneHo Me2NCH2CH20H 30°C ,6h
pH 10.1 pH 11.0
98% 0%
Buonom. ET,; Rosauer,KG.; Dai, L. Tetrahedron Lett., 1995, 36,4o$I
0% 100%
Section 330
Alcohol - Ketone
273
H
K
1. Bu$nH , AIBN, PhH relux
0 -
Ph
2. PhCHO, 10°C, 12h
I
ti
73% (61 erytrho:threo) Enholm. EJ,; WhitIey, P.E. Tetrahedron Lett., 1995, 36, 9157
0
1. SmI2 Br
,
M%5 4
0
2. Hz0
OH
Ph Y
*
77% O Arime, T.; Takahashi, H.; Kobayashi, S.; Yamaguchi, S.; Mot-i. N, Synth. Commun., 1995, 25, 389 DMSO , KSF , microwave, 3 min Ph /\ . . lllemrn
0
OH 0
55%
DJ Hammadi, M. Synth. Commun., 1995, 25, 3141 0
Sm.
Ph *
1. LDA 2. Ti(OiPr)$l
53%
3. TBHP, BaO 4. NH8 , Hfl m; Kluge, R.; SchiiBer, M.; Hoffmann, G. Tetrahedron, 1995, 51, 3175 OH
$ A (CH2)7
Cl3CCO2H , 11°C , Cl2 , MeOH wh9
EtOH, NaHC03
0 w
r
98%
k (CH2)7
CgHW
Tassirznon. P.S.&; De Wit, D.; De Rijk, T.C.; De Buyck, L.F. Tetrahedron, 1995, 51, 11863
Br-COzEt
1.2 q. SmI2, -6OOC --+ -5O.C * 2. cyclohexanone , -50°C -+ 0°C
cC02Et OH
Utimoto. &; Matsui, T.; Takai, T.; Matsubara, S. Chem. Lett., 1995, 197
98%
274
Section 33 1
Compendium of Organic Synthetic Methods, Vo19
1. AlMe I Ph Aoki, Y.; ‘cr
Ph 79% (13:87 erythro:threo)
2. PhCHO i
I(.: Uti moto. K, Chem. L&t., 1995,463
Ph
PhCHO
-78OC ,6.5h Ishihara, K.; Hanaki, N.; Funawashi, M.; Miyata,M.; Yamamoto. 1995, 68, 1721
SECTION 331: ALCOHOL,
THIOL
Ph Bull. Chem. Sot. Jpn.,
- NITRILE
3: 1 EtCN-CH2C12, 1Oh 20% Mg-dihydrooxazolidine
c&3-cHo Corev.EJ.; ww,
OMS catalyst E * ca13>cN 12% bis-dihydro oxazolidine derivative z. Tetrahedron Lett., 1993, 34, 4001 H
4
CN
92h9* 100 units enzyme O.lM citrate buffer
NCHO
)
acN
93%Jz;Fon
enzyme = hydroxynitrile lyase from Hevea brasiliensis Klempier, N.; Ga; Hayn, M. Tetrahedron Lett., 1993, 34, 4769
80% Ohno, H.; Mori, A.; m. 02
88% (95%=, 9
S, Chem. Lett., 1993, 975 1. LiCH2CN 2. H30+ *
cl@21LCN73%
;fIaye. TJL; Crawford, K.B. J. Org. Chem., 1994, 59, 520
Section 33 1
Alcohol - Nitrile
0
275
1. TMSCN , CH2C12 , rt KCN/18-crown-6
0
2. MeOH/THF , SmI2
-
H”-(=)-cN 80%
Olson, S.H.; Danishefskv. SL Tetrahedron Lett., 1994, 35, 7901 OH 5
1. LDA , THF , -78OC
OH CN
ph-CN 2. PhCHO
*
Ph T
CN +
Ph hc
Ph Ph . 1) 70% (5 5 Carlier. P.R; Lo, KM.; Lo, M.M.-C.; Williams, I.D: J. Org. C’hem.,‘1995, 60, 7511 OH [ LDA , PhCH2CN ] , TMSCl
CN
PhCHO
97%
Zhou, J.J.P.; Zhong, B.; mennan.
Ph Rh J. Org. Chem., 1995, 60, 2261 HO
*
PhCHO Me$iCN
, Ti(OiPr)d 72% (91% ee, S)
Balm. C,; Miiller, P. Tetrahedron Lett., 1995, 36, 1625
GoI~~~-~H~ tm;
Cl Cl Zhmg, X.-L.; Han, Y .; Tao, W.-T.; Huann. Y .-2, J. Chem. Sot., Perkin Trans. l., 199% 189 Review:
“Catalytic Asymmetric Cyanohydrin Synthesis,” North. M, Synlett, 1993, 807
276
Section 332
Compendium of Organic Synthetic Methods, Vo19
SECTION 332: ALCOHOL,
THIOL - ALKENE
Allylic and benzylic hydroxylation (C=C-C-H -+ C=C-C-OH, etc.) is listed in Section 41 (Alcohols from Hydrides).
2 MeMgBr , CuCN BF3QEt2, THF
Bn
Bn -78OC
OH E z=
Me
=
88%
S-L; Lee, D-H.; Sim, H-S.; Lim, J-S. Tetrahedron Lett., 1993, 34,91 1. TIPSCl 2. MeLi -L PhCHO
0
.
JNEt2 yJ+L--yw
yj&
L 81%
Tsukazaki, M.; Snieckus. V, Tetrahedron Lett., 1993, 34,411 Lee, J.; Tsukazaki, M.; Snieckus, V, Tetrahedron Left., 1993, 34, 415 2SmI2,r-t 2 t-BuOH , THF
Me0
Me0
Me0
5 +
CHO 7r
I
(2 OH
.
..
3
OH
1) 66%
Glllmann. T, Tetrahedron Lett., 1993, 34, 607
SPh
BuLi , THF , -78OC t
C5Hll
OH Takano. S,; Sugihara, Y.; Ogasawara, K. Tetrahedron Lett., 1993, 34 845
5% DTBB , THF, O°C
<
1 Cl
l.xsLi,2iPrCHO 2. H20-HCl
-
q+%
(1: 1 diastereomers) Guijarro, A.; Yus. M, Tetrahedron Lett., 1993, 34, 2011
SPh 83% 10.8:1 , E.-Z
Section 332
/ PJc
Alcohol - Alkene
277
1. MY::~c~~~~;
+p;
2. NaOH , Hz02 ..
(87
13)
90%
Me
after 24 h at rt Phx>i
I
only product (90%)
OH
D.&; Kim, K.; Martinez, J.P. Tetrahedron Lett., 1993, 34, 3071 1. PhCHO , DMF , 0°C wSC13
y
-
., OH = = Q = = = t.
2
97)
Kobavashi. S,; Nishio, K. Tetrahedron L&t., 1993, 34, 3453
10 eq. BuLi , 10 min )
89%
71%
OH
Bu
Lautens. M,; Gajda, C. Tetrahedron Lett., 1993, 34, 4591 BI-j
B
/-Br
rJ
C&CHO
, EG-Zn e
DMF , O°C ,2h
C3H3
72% EG-Zn = electrogenerated reactive zinc Tokuda. M,; Mimura, N.; Karasawa, T.; Fujita, H.; winome. 7607
H, Tetrahedron L&t., 1993, 34,
PhCHO , hv (>320 nm) EtCN , -78°C ,5h E-snBu3
-
A+&
+ EthPh (30
muwa.
..
k; Shiigi, J.; Nishigaichi, Y. Tetrahedron Mt., 1993, 34, 3457
70) (86: 14 E.z)
278
Compendium of Organic Synthetic Methods, Vo19
Section 332
Et2Zn , Ti(OiPr)d , 12h -6OOC + -55OC
d \
8%
,Ti(OiPrb
(93% ee)
Y
Rozema, M.J.; Eisenberg, C.; Liitjens, H.; Ostwald, R.; Belyk, K.; wel. LAt., 1993, 34, 3115
4
P, Tetrahedron
1,2dichlorobenzene , 12h reflux , CO.5torr
llllI~lll
t
Q
=
90%
bH
*
\
OH Janardhanam, S.; Devan, B.; RaiogoDalan. K, Tetrahedron L&t., 1993, 34,676l 1. Sharpless epoxidation 2. TsCl
Ph OH
78% (>90% ee)
3. Te , LiBHEt3 , THF TBAF,lt
* \ - D-c; Discordia, R.P.; Zhang, Y.; Murphy, C.K.; Kumar, A.; Pepito, A.S.; Wang, Y. J. Org. Chem., 1993, 58, 718 Bu
iPrMgBr , THF Bu
wJP)2Ni2c12
Ducoux, J.-P.; LeMenez, P.; tine&
Bu *
+
h
(CH2)2CH20H
w
u-mCH20H (>25 1) 60 N... Wenkert. E, J. Org: Chem., 1993, 58, 1290
MeJSiSnBu3 , DMF 86%
CsF, rt, lh *b mu;
OH Isono, N.; Kaneta, N.; Shibasaki, M. J. Org. Chem., 1993, 58, 2972
Section 332
Alcohol - Alkene
279
OH w
hv,CO,THF,8h
c. CA;
75
Xu, D.; Gladstone, B.G. J. Org. Chem., 1993, 58, 538
0
EtMgBr , 10% Zr complex THF ,25*C
0
Morken, J.P.; Didiuk, M.T.; Hove-
OTMS
65% (>97% ee) A.H, J. Am. Chem. Sot., 1993, 115, 6997
5% (binol)TiClz , BnOg-CHO C02Bn Me
63% (99:l syn:anti; 99:l ZE; 99% ee, R) Mikami. K.; Matsukawa, S. J. Am. Chem. Sot., 1993, 115, 7039
‘* --cbv
SiMe3 ’ “:‘igchiral ligmd
phu
*
PhCHO
Z = = 63% (92% ee)(96:4 erythro:threo) bH Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H,J. Am. Chem. sot., 1993, 115, 11490 2. TBAF
OH --i=h’
, 10% Pd(OAc)z
2 Na02CH ,2 BuflCl ,2 iPr2NEt MezNCOMe ,8O*C, Id ~R.c.;
Ding, S.; Tu, C. Synlett, 1993, 145
70% (5644 E.-z)
280
Compendium of Organic Synthetic Methods, Vo19
Section 332
x= Sin&ton.
D.A,; Redman, A.M. Tetrahedron Lett., 1994, 35, 509
&,gmak. J.D,; Geng, B.; Uang, S.; Strickland, J.B. Tetrahedron Lett., 1994, 35, 985 1. Cp$Zr(H)Cl , CH$12 2. Me2Zn
Bum
3. PhCHO , O°C
Bu 94%
WiDf. P,; Xu, W. Tetrahedron Lett., 1994, 35, 5197 /\/\oO
2eq. Me#=CH2
,THF
*
z
-1OOC + rt 80% OH Alcaraz, L.; Hamett, J.J.; Mioskowski, C.; Martel, J.P.; Le Gall, T.; Shin, D.-S.; Falck, J.R. Tetrahedron Lett., 1994, 35, 5449
0 /
/
1. ($-C$-I,hTiCl \
iPrMgC.1, THF , -50°C 2. PhCHO , -50°C +
= -20°C
@Ph+
@Ph (1.44
:
1) 42%
Szymoniak, J.; Felix, D.; Moi’se. C, Tetrahedron Lett., 1994, 35, 8613
1. HSiC13 , cat. Pd(PPh& 2* Phw
CHo , DMF
Kobavashl, . S .; Nishio, K. Synthesis, 1994, 457
Ph 87% (>99: 1 syn:anti)
Section 332
Alcohol - AIkene
phCN,Nyluene9
281
refhx, 3hwfiMe 73% Ph
(3:2 synxnti)
Kim. S,; Cho, C.M. Tetrahedron Lett., 1994, 35, 8405
Pd(OAc)z ,3 PPh3 , PhH 7O*C, 16h
CHO
-5
OH 47% Watanabe, T.; Sakai, M.; Miyaura, N.; Suzuki, A,.!. Chem. Sot. Chem. Commun., 1994,467 OH
BuMgBr N-NHTs
* .,,t5L Takhi, M.; Yadav, J.S. Tetrahedron Lett., 1995, 36, 307
Chandrasekhar.,
1. Li , NH3 , THF-EtOH 2. TBAF , THF
Bu
, -78OC
\* ,, ,*’ *
3.30% aq. H202, KHCO3 , MeOH OH Taber. D.F*; Yet, L.; Bhamidipati, R.S. Tetrahedron Lett., 1995, 36, 351
5% Pdz(dba)3*CHC13 , THF 20% PPh3 , heat \ MpM(,o
OH
93% KanG S-K,; Park, D.-C.; Park, C.-H.; Hong, R.-K. Tetrahedron Lett., 1995, 36, 405 Phs
1. Cp2TiClz/2 BuLi , 0°C 2-
ma.
PW
CHO
T,; Miura, I.; Horikawa, Y.; Fujiwara, T. Tetrahedron Lett., 1995, 36, 1495
282
Compendiumof Organic Synthetic Methods, Vol9
Section 332
Co(tdcpp) = [5,10,15,20-tetrakis(2,6-dichlorophenyl) porphinato] Cobalt (II) -Y.; Sugamoto, K.; Nakama, T.; Sakamoto, T.; Matsui, T.; Nakayama, M. Tetrahedron Lett., 1995, 36, 18’79 Ph
Ph 3 t-BuOK, BuLi THF , -78OC
OH *
R=TBS (79 R=H (20 Tomooka, K.; Keong, P.-H.; Nakai. T, Tetrahedron L&t., 1995, 36,
.. .
21) 48% 80) 90%
&89
1. BuLi, THF , -78°C 2. PhCHO, -78OC -+ rt
+
PhxH
/= 85%
MO, X.-S.; uuang. Y.-Z, Tetrahedron Lett., 1995, 36, 3589
&
OMe Dibal , 14% Ni(cod)z 20% R-BINAP , lh i-l
OMe
*
H
htens.
78% (97% ee) M; Chiu, P.; Ma, S.; Rovis, T. J. Am. Chem. SOC.,1995, 117, 532
‘OMe
Aldehyde - Amide
Section 335
283
Ph SnCb-NBu3 , MeCN reflux Yamaguchr. b&; Hayashi, A.; Hirama, M. J. Am. Chem. Sot., 1995, 117, 1151
S.-K,; Park, D.-C.;
Rho,
H.-S.; Yu, C.-M.; How
J.-H,Synth. Commun., 1995, 25,
203 OMe =c
PhCHO .
9 10%Ti(OiPr)d
20% chiral binaphthylamine
Bemsford.
.
C, Angew. Chem. Znt. Ed. Engl., 1995, 34, 1717
Also via:
Section 302 (Alkyne - Alcohol).
SECTION 333: ALDEHYDE
- ALDEHYDE
NO ADDITIONAL EXAMPLES
SECTION 334: ALDEHYDE
- AMIDE
S02Ph
SO2Ph Brown, S.; Clarkson, S.; Grigg. RJ Sridharan, V. J. Chem. Sot. Chem. Commun., 1995, 1135
SECTION 335: ALDEHYDE
- AMINE Cl DMF , POC13 8%
Balasundaram, B.; Venugopal, M.; Permumal.P.T, Tetrahedron Lett., 1993, 34,4249
284
Compendium of Organic Synthetic Methods, Vo19
SECTION 336: ALDEHYDE
- ESTER
NO ADDITIONAL
SECTION 337: ALDEHYDE
EXAMPLES
- ETHER, EPOXIDE, THIOETHER
ct
Wp-OMe)2KOD)2
10 eq. PPh3 , CO, H2
+
+ HC(OEt)3 ,2d (96 + HC(OEt)3 + PPTS ,12h (0 Femandez, E.; B. S, Tetrahedron Lett., 1994, 35, 2361 2% Pd(PPh3)4,5 atm CO, THF C5Hll
4) loo)
PhSH , 70°C , 16h
Et0 quant. quant.
CHCHO PhS
Ogawa. &; Takeba, M.; Kawakami, J.; Ryu, I.; Kambe, N.; &poa 1995,
82% (13:87 E.-Z) N, J. Am. Chem. Sot.,
117, 7564
SECTION 338: ALDEHYDE
- HALIDE, SULFONATE
NO ADDITIONAL
SECTION 339: ALDEHYDE
SECTION 340: ALDEHYDE
EXAMPLES
- NITRILE
NO ADDITIONAL
SECTION 341: ALDEHYDE
EXAMPLES
- KETONE
NO ADDITIONAL
EXAMPLES
- ALKENE
For the oxidation of allylic alcohols to alkene aldehydes, also see Section 48 (Aldehydes from Alcohols).
CHO
1. Cp$r(Cl)CH=CHOEt cat. AgClO4
2.H3O+ oMaeta, H.; Suzuki. K, Tetrahedron Lett., 1993, 34, 341
OEt
C5h *
L
Section 341
285
Aldehyde- Alkene
Section 341
Li 1.
OMe
-78OC+ 0°C
PhCHO 2.1N
*
CHO P
HCl , OmC
75%
Duhamel, I,,; Duha.mel,P.; Le Gallic, Y. Tetrahedron Lett., 1993, 34, 319
OTMS 0 I
-
OTMSCAN, MeCN , O°C
Paolobelli, AX; Latini, D.; Ruzziconi.
25%
CHO
Tetrahedron Lett., 1993, 34, 721
polymeric Fe catalyst
Saha,AK.; Hossain. M.M, Tetrahedron Lett., 1993, 34, 3833 Br
CHO 6\
/
9 (3-W& 79%
cyclic B catalyst, -78°C ,8h
(99:l exxendo) ,92% ee Corev. E.J,; Loh, T.-P. Tetrahedron Lett., 1993, 34, 3979
PhCHO
CsF-DMSO , rt + loO°C
*
PWCHO
ZnClz, rt ,2h &; Salemkour, M. Tetrahedron Lett., 1993, 34, 5281
70%
2.
md.
7=-i
PhCHO ,5% TfSiMe3 CH2C12, rt ,15h
P
v MqSi CHO OSiMe3 Duhamel. L; Gralek, J.; Bouyanzer, A. Tetrahedron Lett., 1993, 3% 7745
80%
Com~n~um of Organic Synthetic Means, Vol9
286
N-t-Bu md.
WI,: 1187
PhCHO , 10% ZnBrz , THF
(Me3Si)zHC J a; Majidi, A. J, Org. Chem., 1993, 58, 2517 m
/CHO
Section 341
SnBq
, CgHlyBr, AIBN
20 atm. CO, PhH , 80°C, 8h
Yamazaki, H.; Ogawa, A.; Kambe, N.; ma.
1.
9 0
74% N, J, Am. Chem. Sot., 1993, 115,
, acetone
a2. PH3P=CHCH0, CH2C12
‘“~0, 84%
Adger, B.J.; Barrett, C.; Brennan, J.; McGuigan, P.; Wervey. Commun., 1993, 1220
M.A, J. Chem. Sot. Chem.
HO , SmI2,25OC
CHO (955 Van de Weghe, P.; collin,
[1,4:1,3])
72%
Tetrahedron Lett., 1994, 35, 2345
Bu 1. Bu$H , TiCI , CH2Cl2 2. F’OC13 , DMF , O-5OC
67%
*
~
CHO
Asokan. CV,; Mathews, A. Tetrahedron Lett., 1994, 35, 2585
75 Derien, S.; Dixneuf. P.I-I, J. Chem. Sot. Chem. Coals.,
25) 85%
: 1994, 2551
Ph-OH
287
Amide - Amide
Section 342
Pd(PPh3)4 , NH4PF6 , toluene - phmcHo 02 , heat
90% Gomez-Bengoa, E.; Noheda, P.; Echavarren, A.M. Tetrahedron Lett., 1994, 35,7097 Et0
SnBu,
1,
PhCHO
ph/n/CHO
BF3mOEt2, CH2C12, -78OC, lh 86% Cabezas, J.A.; Oehlschlaner. AC, Tetrahedron Lett., 1995, 36, 5127
.
Mn02, hexane, 15 mm
ph-N,OH
*
phmCHo 87%
Shinada, T.; Yowa.
L Tetrahedron Lett., 1995, 36, 6701 CHO Ru (indene)Cl(PPhg)z
88%
-i_i
Ph
Ph
Trost, B.M.; Livingston, R.C. J. Am. Chem. Sot., 1995, 117, 9586 CHO
2% [ Rh(CO)z(acac) ] +
C3H-W7
2.2% biaryloxyl phophite
Johnson, J.R.; Cuny, G.D.; mwald.
SLAngew.
A C3H7
w7
85% Chem. Int. Ed. Engl., 1995, 34, 1760
Also via P-Hydroxy aldehydes: Section 324 (Alcohols - Aldehyde).
SECTION 342: AMIDE - AMIDE NO ADDITIONAL
Also via Dicarboxylic Acids: Diamines
EXAMPLES
Section 312 (Carboxylic Acid - Carboxylic Acid) Section 350 (Amines - Amines)
288
Compendium of Organic Synthetic Methods, Vol9
Section 343
SECTION 343: AMIDE - AMINE Me C=N
AcCl , Ac20 , HCl 63%
100-130°C) 4h
NHAc Me Vijn. R.J,; Arts, H.J.; M aas, P.J.; Castelijns, A.M. J. Org. Chem., 1993, 58, 887 l.TMSCI,NaI,12 TMEDA , MeCN 2. NH3, loO°C 3. racemization-resolu tion
o-II& K.L; Keller, J.L.; Purick, R.M Hartner Jr., F.W.; Choi, W.-B.; Askin, D.; Volantei R.P. Tetrahedron Mt., 1994, 35, 32i9 l
TsHN \
Pd(OAc)z , EtzNH latmCO,THF
P
,-Ts
CH2Ch
. Andersson. PeGI; Aranyos, A. Tetrahedron Lxtt., 1994, 35,444;
/ \ I q
14) 72%
Me -7OOC + -2OOC
N
I N
t Ph
OZnCl OMe
Me0
58%
Me van Maanen, H.L.; Kleijn, H.; Jastrezebski, T.B.H.; van Koten. G, Reel. Trav. Chim. Pays-Bas, 1994, 113, 567
Section 344
Amide - Ester
T
289
S
N
BnNH2,10%
NHTs
Yb(OT&
CH2C12, rt, 1Oh
NHBn
ANHBn
‘arts
A
(>99 : 1) Meguro, M.; Asao, N.; Yamamoto, Y. Tetrahedron L&t., 1994, 35, 7395
CL N
0
t-BUN& , NEt3
)
0%
N
75%
0
78%
CH2C12, reflux , Id I Cl NHt-Bu Chen, P.; Suh, D.-J.; Smith. M.B, J. Chem. Sm., Perkin Trans. I., 1995, 1317 L
SECTION 344: AMIDE - ESTER t-BuBr , KgO3, DMAC BTEAC ,55OC * Boc
92%
BocH DMAC = dimethyl acetamide BTEAC = BuEt3NCl Chevallet, P.; Garroust, P.; Malawska, B.; Martinez. J. Tetrahedron L&t., 1993, 34, 7409
Mn(OAc)3 , CH$O2Me)2
Chuang. C-P,; Wang, S.-F. Tetrahedron Lett., 1994, 35, 1283
a;
Lee, S.J. Tetrahedron Lett., 1994, 35, 1875
290
Section 345
Compendiumof Organic Synthetic Methods, VoI9
1.15% ZnCl2 CH2C12 2. CAN, M&N, CO
Ph
Ph Chen, T.; Jiang, S.; mos. E, Tetrahedron Lett., 1994, 35, 8325
Y
Cl
CO2Me Bu3SnH , AIBN , PhH *‘h0
N’Bn
Ph “i( 0
N I Bn
2:
C&Me
Ph 0
52% Goodall, IL; Parsons.A.F, J. Chem. Sot., Perkin Trans. I., 1994, 3257 0
1. Sn(OTf)z CHz,Clz
0
C02Me
~
N-- Et
c
2.
N
**
c-l
I
OEt
COzMe
C02Et
‘;J
CO,Et
78% Nagasaki; Nishida, S.; Sugihara,S.; Kawahara,T.; Adachi, K.; Hamaguchi,F. ~etero~c~s, 1994, 39, 171 Section315 (Carboxylic Acid - Amide) Section316 (C~~xy~ic Acid - line) Section 351 (Amine - Ester)
RelatedMethods:
SECTION
345: AMIDE
- ETHER,
EPOXIDE,
THIOETHER OH
CO/H2 (1600 psi) ,loO*C HC(OEt)3,24h H~(CO)(PPh)3 OSiMe3
42% OEt
0
(2: 1 syn:anti)
Eguchi, M.; Zeng, Q.; Korda, A.; Qiioma. I, Tetrahedron Lett., 1993, 34, 915
291
Amide - Ether
Section 345
1.
P-O H
Ph Ph
J3H3,TNF
w
2. H+ , EtOH Bn Romagnoli, R.; Roos, E.C.; Hiemstra. H,; Mollenaar, M.H.; Sneckamp,W.N.; Kaptein, B.; Schafer, H.E. Tetrahedron Lett., 1994, 35, 1087
H
Ar
Ar = 4-nitrophenyl; Ar’ = 4-t-butylphenyl
95% (66% ee) Hayashi, M.; Ono, K.; Hoshimi, H.; Qgni. N, J. Chem. Sot. Chem, Commun., 1994, 2699
cyclohexanone, H$X&
CN AcOH , Ac20, 10°C , Ih a&. J.-F,; Jung, L.; Hug, R. Heterocycles, 1994, 38, 297
cat. ZnC12, CH2C12,50°C16d ~y~e~ic
Pummerer rearrangement
; Shibata,N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K. Tetrahedron Lett., 1995, 36, 115
Section 346
Compendiumof Organic Synthetic Methods, Vo19
292
C@Me
Amlres, C.J.; Spetseris,N.; Norton
SECTION 346: AMIDE - HALIDE, SULFONATE
Cl * l-L?Cl
Cl
CuCl , cat. bipy
98%
0
N
I Bn
Nagashima,H.; Ozaki, N.; Ishii, M.; Seki, K.; Washiyama,M.; Itoh, K. J. Org. Chem., 1993, 58,464
Et3N*3 HF , MeCN
77%
t e”
Narizulca, S.; Fuchierami. T, J. Org. Chem., 1993, 58, 4200
IP
Ph#e(OH)OAc , I2 hv ,6Sh ;)
0
I
I
76% Dorta, R.L.; Francisco, C.G.; Suarez. IE,~etr~he~~~~ Lett., 1994, 35, 1083
a
NPh2
w ~
.
h/L; m
1. b-AnP(S)S]z, PhMe , lOO*C 2. Bum2F3, NIS , CH2C12 o”c -+ l-t T, ~etr~he~~u~ Lett., 1994, 35, 3983
F w w
x
F
NPh2 98x64%
Section 347
Amide - Ketone
293
C3H7
0 b Nt
0
-7VC, 6h BC120Me
ind Jt-
1) 80% o. G,; Di Martino, E.; Gentilucci, L.; Tomasini. C,; Tomioni, L. Tetrahedron Asymmetry, 1995, 6, 1957 (>99
l
SECTION 347: AMIDE - KETONE
0
2DMP,4Py,lh CH2Clz, rt
N
Dess-Martin
ti
)
0 N
0
periodinane
Ph
75%
Ph
,hyr DMP = 1,1,l-triacetoxy-l,l’-dihydro-l,2-benzodoxol-3(1H)-one Batchelor, M.J.; Gillespie, R.J.; Golw. J.M.C,; Hedgecock,C.J.R.
Tetrahedron Lett., 1993, 34, 167
30% H202, Pd(OAc);! CH2C12,rt ,2h -
73% *
Naota, T.; Sasao,S.; Tanaka,K.; Yamamoto,H.; Murahashl.. 4843
0
0
ii Tetrahedron Lett., 1993, 34,
OEt
w
c
0 TFA , 20°C, Id N
NT -* 0 Br 0 J.-P*;Jacquesy,J.-C.; R~nbaud, D. Tetrahedrons 1993, 49, 2239
47%
Section 347
Compendium of Organic Synthetic Methods, Vol9
294
Bu$nH, AIBN, PhH (syringe pump addition) a 91%
Beckwith. A.L,J,; Joseph, S.P.; Mayadunne, R.T.A. J. Org. Chem., 1993, 58, 4198
1. 3 Mn(OAc)3 2. H30+
+
h /
N
cossy. J,; Bouzide, A.; Leblanc, C. Synleft, 1993, 202 OTMS Me$iOTf
NMeC02Mk
, NEt3
NMeC02Me
O°C , lh Rossi, L.; J?ecumo. OMe
A, Tetrahedron Lett., 1994, 35, 5285
)I
Hewawasm
3.12N HCl-DME , reflux /
Me 0
1. BuLi, THF, O°C 2. (C02Et)2
\ I b
85%
\ I fi
0 /
NHCOzt-Bu P,; Meanwell, N.A. Tetrahedron Lett., 1994, 35, 7303
PhCH=NC02Et,
BF3eOEt2
CH2C12, rt ,2d ten Hoeve, W.; Wynberg, H. Synth. Commun., 1994, 24, 899
N \ H
80x88%
section 347
Amide - Ketone
295
Me I
1. Me~OH
Ph
0 N-Me
2.
60% via heteroCope 3, Hz0 Lantos, I.; Zhang, W.-Y. Te~$~~e~r~~ L&t., 1994, 35, 5977 0
OMe Si(iPr) 3
1. RCOCl 2. MeMgX 3. oxalic acid 4. TFA , CHC13, heat + ,yyi+* ,\* i) N
I
I 78~86% I CO2R
R = (-)m8-phenylmen~yl Comins. D.L,; LaMunyon, D.H. Tetrahedron Lett., 1994, 35, 7343
1. t-BuLi , TMEDA , -78OC NiPr2
t 2.
Brenstrum, T.J.; Brimble. M.A,; Stevenson,R.J. Tetrahedron, 1994, 50, 4897 0
NHAc
\ I /I phi 0
CoCl2, MeCN, AcCl
Bhatia, B.; Reddy, M.M.; Iqbal. J, J. Chem. Sot. Chem. Commun., 1994, 713 b
NfIMe
4 eq. DMAP , toluene , reflux
N
/
Me
w
c0ssv.z.; Belotti, D.; Bouzide, A.; Thelland, A. Bull. Sot. Chim. Fr., 1994, 131, 723
NO2
Section 349
Compendium of Organic Synthetic Methods, Vol9
2%
0
* 0”
l.e-,AcOH,heat 2. MeOH, NazCO3
0
75x95% N N I I C02Me C02Me Matsumura. Y.; Takeshima, Y.-i.; Okita, H. BUZZ.Chem. Sot. Jpn., 1994, 67, 304
iPrCH0, AcCl ,02, CoC12 = Reddy, M.M.;
MeCN Bhatia, B.; -1.
76%
J, Tetrahedron Lett., 1995, 36,4877
0 cat. [Rh2(OAc)4] B-‘&/2
=: = z
*
59%
Ge Podlech, J.; Seebach. D, Helv. Chim. Acta, 1995, 78, 1238
SECTION 348: AMIDE - NITRILE 0
0 CN
IIZN JL
Ph
CN
DMSO, O2 Ph
88% Jain, R.; Roschangar, F.; Ciufolini. M.A, Tetrahedron Lett., 1995, 36, 3307
SECTION 349: AMIDE - ALKENE
.. (6 Khiar. NJ Femandez, I.; Alcudia, F. Tetrahedron L&t., 1993, 34, 111
4
78%
297
Amide - Alkene
Section 349
1. LDA , THF , -78OC ApcPh
92%
PhR 2. PhCHO , THF Ph I /q II I ph reflux Me Me 0 ; Deniau, E.; Grandclaudon,P. ~~tr~h~~ron Lett., 1993, 34, 1479
0\ /
0
0
lm%z
, MS481, CH2C12
0
*
20% chiral Yb triflate , O°C
~~ .
I(lobavashl.;
(89: 1 en.do:exo; 95%ee) Hachiya, I.; Ishitani, H.; Araki, M. tetrahedron Lett., 1993, 34, 4535
4% Pdz(dba)3eCHC13 9.6% RS-BPPFOH silver~xch~ged zeofite c ~~ ~
D~:DMSO
0 (1
0
Tetrahedron ktt.,
Nukui, S.; Sodeoka,M.;
Bf R -dFoEt
+
, WC, 5d
\
*.
1.4) 94% (86%ee)
1993, 34,4965
, PPh3 /n-IF
Ph
f14$.?
R
Ph
2% Pdz(dba)3~HCl3 2 eq. iPr2NEt
OEt
-
g
0
N \
73%
Bn Torii. &; Okumo~, H.; Sacked M.; Hai, A.K.M.A.; Tanaka, H. tetrahedron Lett., 1993, 34, 6553
0\ I
) -20”C, 36h
Ph
w
b&imine*cu(OTE)2 (>97:3 en.do:exo) 72% Evans. D,A,; Lectka, T.; Miller, S.J. Tetrahedron Mt., 1993, 34, 7027
298
Section 349
Compendium of Organic Synthetic Methods, Vol9
1.. 0.2 eq.fe(acac)s 3 eq. EtjAI/L
0
o+
2. ethylene glycol cat. p-TsOH cc BzO
ws.
m;
Weidner, J.J.; Takacs, B.E. Tetrahedron Mt., 1993, 34, 6219
0.02 PdC12,2 eq. CuCL2 3 eq. ClCH,CQ-Na+ NHTs 9(
C02Me
CO. MeOH
N\
53%
Ts
Y
0
0 Kimura, M.; Saeki, N.; Uchida, S.; Harayama, H.; Tanaka, S.; Fugami, K.; Iama~~ Y, Tetrahedron Lett., 1993, 34, 7611 1. Et02C-N=N-COzEt , SnC4 CH2C12, -60°C, 5 min
2 N-J-N
*
*mC02Et
2. Li , NH3 , -33°C 3.10 N HCl Brimble, M.A.; -cock.
CL
87 x 86% (1l:l
E:Z)
J. Org. Chem., 1993, 58, 5261
Br Pd(OAc)z , P(o-ToI) , DMF Na$ZOs, BUflCl ,65”C, 40h sealed tube (in vacua) 4iEs+
&
1) (4 Harris Jr., G.D.; Herr, R.J.; Weinreb. S.M, J. Org. Chem., 1993, 58; 5452 l
78%
Amide - Alkene
Section 349
299
Pd(PPh3)4,PhMe ,lOO°C Trost. B.M; Marrs, C.M. J. Am. Chem. Sot., 1993, 115, 6636 COzBn Ph$‘=CHCO2Et *
80%
toluene , reflux ,4h
Et0 \ ~ Ba: 0 BOC Baldwin. JE,; Edwards, A.J.; Farthing, C.N.; Russell, A.T. Sy~lett, 1993, 49 CO2Me
1. NaH , THF , BuLi CO2Me Ts
>96% (>20:1 E=z)
3. toluene , Amberlyst 15 , reflux &p
B, Sy~~ett, 1993, 764 Ph PhCH2m2Et
Ph
1.2 eq. LDA 2. Ph~H=NPh
*
PhHN 7
58% 0 this reaction forms a p-lactamwith 1 eq. of LDA Manhas. M.S; Chaudhary, A.G.; Raju, VS.; Robbi, E.W.; Bose, AK. HeterocycZes, 1993, 35, 635
1. xylenes , reflux 2. PPTS NaH , DMF THPO’ De la Torre, J.A.; Femandez,M.; mJr.. Tetrahedron Lett., 1994, 35, 15
60% 68~75% D,; Smith, D.B.; Talamas,F.X.; Trejo, A.
OMe Zn,THF,rt,lh NHCaMe Kise. N,; Yamazaki, H,; Mabuchi, T.; Shono, T. Tetra~e~r~~ Lett., 1994, 35, 1561
300
Section 349
Compendiumof Organic Synthetic Methods, Vol9
79% W,; Fiirstner, A. Helv. Chim. Actu, 1993, 76, 2329
Qpolzer.
1. piperidine , CF3C@Ag --YSPh
THF’rt 2. CgHl@gBr NiCl,(dppe)
6
* csH1& , THF , 0°C + rt 57x60%
a
B&u&-i, F.; Fiandanese.V,; Naso, F.; Punzi, A. Tetrahedron Lett., 1994, 3.5, 2067
6 i/
PhMe2CCH=Mo-N[2,6-(iPr)2C6H13] [ocMe(CF3)212
N-0
I
a@
PhH,rt
0
80-90%
/
n. S.F,; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser,M.N. Tetrahedron Lett., 1994, 35,
&‘Ph3
SO2Ph
Burley, I.; Hewson. A.T, Tetrahedron Lett., 1994, 35, 7099
COzt-Bu
C02t-B u 52% (9O:lO E:Z)
Wei, Z.Y.; m.
EL Synlett, 1994, 345
Section 349
Amide - Alkene
301
0 ==cIl N
, MS 4A, CHg12
alto
N CA
/ N
20% Yb-BINOL complex 7
0
c-J== 0
Me
0
.t
(89
11) 77%
95% ee Ishitani, H.; Araki, M.; Hachiya, I. Tetrahedron Lett., 1994, 35, 6325
.
WS.;
0
C02Et NH2
1. C02Et
.
Me”“’ rl Ph
H
, BF3GEt2, PhH , reflux
2. CH2=CHC02C@,
0
TI-IF , reflux
+Jz+If2
N
Me”““’ri Ph
H 76% (97:3)
Barta, N.S.; Brode, A.; Stille. J.R,J. Am. Chem. Sot., 1994, 116, 6201 Ar NH2
H2C0, [Rh(OAc)d2, PPh3, PhH -Iso 0
N I 40% H Campi, E.M.; Chong, J.M.; Jackson. W.R,; Van Der Schoot, M. Tetrahedron, 2994, 50, 2533 Ar
aI/ \
NHTs
I
I
Ts CsI-I17--CH=C=CH2 Ag3P04, 5% Pd(OAc)z
/ w-h7
his-oxazoline catalyst 90°C, Id, DMF 94% (82% ee)
Larock. RC,; Zenner, J.M. .I. Org. Chem., 1995, 60, 482
302
Compendium of Organic Synthetic Methods, Vol9
Section 349
Ph-N=C=O , AlC13 ,4O”C Men&Me
ti
NHPh
Me 9
3
CH2C12, 12h 0 Niestroi. M,; Neumann, W.P.; Thies, 0. Chem. Ber., 1994, 127, 1131
50% (4.9:1 E:Z)
BQNF ,66OC
Bn Jacobi. P.A,; Brielmann, H.L.; Hauck, S.I. Tetrahedron L&t., 1995, 36, 1193 Bu 5% C12Pd(PPh&, MeOH, 65OC *
CO (1 atm) ,4 NEt3
AcAB’
ci,
0
N I AC
78%
Coperet, C.; Sugihara, T.; Nenishi. E, Tetrahedron L&t., 1995, 36, 1771 phwTePh
TsNNaCl , EtOH ,20h 25OC
Nishibayashi, Y .; Srivastava, SK.; Ohe, K.; Ueu
c),
-‘“‘f‘
+PhyNHTs
OH 9% 84% Tetrahedron Lett., 1995, 36, 6725
1. LiHMDS , THF , HMPA , -78OC 2. PhNTf2, -78OC + 25OC
cl
t
N o 3. PhguLi , THF-HMPA I -78OC + 25OC Bz Tsushima, K.; Hirade, T.; Hasegawa, H.; Murai. A, Chem. Lett., 1995, H Me+,,,,
I 9(
Me 0.1 AgNCO , 0.1 NEt3 , PhH 50°C, 5h NHTs
N I Bz 801
94x69% Ph
-w/r”“’ N-Ts
-lf
0 0 Kimura, M.; Tanaka, S.; Tamaru, Y kBull. Chem. Sot. Jpn., 1995, 68, 1689
98%
Section 350
Amine - Amine
303
Also via Alkenyl Acids: Section 322 (Carboxylic Acid -Alkene)
SECTION 350: AMINE - AMINE In , aq. EtOH , 16h ) NH&l
N /Ph PhJ
Ph Ph NHPh quant.
NHPh Kalvanam. N,; Rao, G.V. Tetrahedron Lett., 1993, 34, 1647
Plaquevent. J.-C,; Chichaoui, I. Tetrahedron Lett., 1993, 34, 5287 NH
PhCN H
quant.
* G+ Ph Rousselet, G.; Candevielle, P,; Maumy, M. Tetrahedron Lett., 1993, 34, 6395
NHEt2 ,0.8 GPa , CH2C12 ,2d MeOH, 50°C \
H
68% H Matsumoto. K,; Uchida, T.; Hashimoto, S.; Yonezawa, Y.; Iida, H.; Kakehi, A.; Otani, S. Heterocycles, 1993, 36, 2215
/
Br
1. t-BuLi , -78OC , THF 2.ZnC12 3. PdC12(PPh3h , Dibal THF , reflux * w
SiMeg-Bu
Br
/
\ Ior) \
4. TsOH , EtOH Amat, M.; Hadida, S.; Bosch., J. Tetrahedron Lett., 1994, 35, 793
/
93%
N \ SiMe$-Bu
Compendiumof Organic Synthetic Methods, Vo19
304
AI,KOH,MeOH,rt,lOmin 2 ph-
Section 351
Ph
Ph
t
NPh
PhHN Baruah, B.; ~ajapa~, ID.; mu.
NHPh
90% (70:30 dlmeso) J& Tetrahedron Lett., 1995, 36,6747
(95 N&
Nh
. OH Ar = 4-OMe phenyl Shimizu, M.; Kami, M.; EU,jisawa.T, Tetrahedron Lett., 1995, 36, 8607
5) 71%
l
SECTION 351: AMINE - ESTER
C
1.
COzEt ~echoech~;
COzEt
I”
2, SmI2, THF ,25OC 70%
Fem~~dez-Acebes, A. Tetr~~dro~ Lett., f993,34,549 Ph \
N I
1. ImzCO , BF3*OEt2
PhHN
84%
c( 7
TMS
AgF , EtOAc >
s
MeCN , rt 15 min TM:
(17 m.
COzMe
‘t
THF , heat Y 2. NaOMe , MeOII/THF 94% ph S,; D&u, M.D.; CarkSn,R.P. Tetrahedron Lett., 1993, 34, 725 PhA
m.
N-H
(7:3 de) G; Lakshmaiah,G. Tetrahedron Lett., 1993,34,4861
..
SC ss, C02Et 3)
98%
Section 351
305
Amine - Ester
I\ P
1.
, BEt3, DMSO C02Et
54%
Fe2(SO)3~H20, hexane
. Me ch;L,E;,Muraglia, E. Te~rah~dru~ Let?., 1993, 34, 5015 Ph Ph
OMe
78:22 (anti:syn) * dried under microwave condi~ons Texier-Boullet. F,; Latouche, R.; Hamelin, J. Tetrahedron Let?., 1993, 34, 2123
m. .
P,; Pastor,A.; Vilaplana, M.J. Tetrahedron Lett., 1993, 34, 3773
1. Na+ NHS02Tol,60°C THF/DMSO, 19h ) M~~Npha~ -0Ac 2.03, NaOH/MeOH -78OC, 3h Jumnah, R.; Williams. J.M.J, Tetrahedron L&t., 1993, 34, 6619
<
C02Me
1. SnC1,, PhCN
C02Me
2. OH- , Na2C03
73x66%
Ph
C02Me
w H
CO2Me
H2N
91% Nicolini. MJ Citterio, A. Org. Prep. Proceed. In?., 1993, 25, 229 NHPh PhCH=NPh , CH2C12,-78*C ,2h
COzEt
Fe-Mon~norilloni~
WM.;
97% (96:e threo:erythro) Ohno, R.; Yanigiya, N.; Izumi. Y,Synlett, 1993, 141
Com~n~um of Organic S~~e~c Mean,
306
V&9
section 351
77%
Bureau, R.; Mortier, J.; Joucla, M, Bull. Sot. Chim. Fr., 1993, 130, 584
Bu$nCH$02Et,
ClC02Me
t
-4OOC -+ rt
Q&U, T.W,
Gluchowski, C. Tetrahedron Lett., 1994, 35, 989
EO2
MeO$X=CC@Me DMSO , MS 4pi MeA
Me02
02Et
c
+
135°C
* (36 Jiang, S.; Janousek, 2.; Viehe. H,G, Tetrahedron Lett., 1994, 35, 1185 l
64) ‘72%
400~5OO”C,16 torr 60%
Me-* c2 much lower yields with S-memberedrings
0
OH Jourdain, F.; &mm&$. J.C. Tetrahedron Lett., 1994, 35, 1545 LiBHEt3, SiHEt3 C02Et
BF3eOEt2
C02Et 85%
Pedr@. C,; Ezquerra,J.; Escribano,A.; Carrefio,MC.; Garcia Ruano,J.L.G. Tetrahedron Lett., 1994, 35, 2053
Amine - Ester
Section 351
2 eq. CO ) SnC12
307
C&Me
m
PdC12(PPh3)2
62%
H Akazome, M.; Kondo, T.; Wata;nabe.YJ
Org. Chem, 1994,59,3375
1. BBr3 2. Hz, Pd-C , AcOH
J&f&d. cl.& Thornton, S.R.; Sienkiewicz, K. Tetrahedron Lett., 1994, 35, 3905 Bn CbzHN
Bn
BOP , MeOH, CH2Cl2 -2OOC -+ rt
WZH
97%
* CbzHN
U&Me
BOP = benzotriazol-1-yloxy(dimethylamino)phosphoniumhexafluorophosphate Kim, M.H.; &gel. D.V, T~tr~h~~r~~ Lett., 1994, 35, 5603
Bn I
Meo2w(-02Me
T”S\/N\/mS
Bn
es, AcONa 47%
Okumoto, H.; Genba, A. Sydett, 1994, 217 BnNH12,10%La(OTf)3, -C02Et
CH2C12
l-t
C02Et NHBn 95%
Matsubara, S.; Yoshioka, M.; -0.
K Chem. Lett., 1994, 827
* PhH , AIBN , heat
Willies, ams,L. J, them. Sot. Chem. C~rn~~~., 1994, 883
308
Compendium of Organic Synthetic Methods, Vo19
C02Me
/
Section 35 1
(~PI-)~NH, 50°C, 3 K&u -
(Pri)2Nwco2Me
cat. Yb(OTf)3
80% (13% with no catalyst 17% with catalyst at 1 Bar) Jenner. G, Tetrahedron Lett., 1995, 36, 233
1.3 eq. bu$nI-I ,0.15 AIBN PhH (0.025 M) , reflux ,6h )
Br N/n/C02Et
syringe pump addition, 5h
I 602Me UE.; 417
/(&C02Et I C02Me
96% (59:41 - trans:cisI) Kang, T.S.; Joo, B.J.; Tae, J.S.; Li, KS.; Chung, C.K. Tetrahedron Lett., 1995, 36,
H I
1. DMSO , (COC1)2 70% 2. NEt3
C02Me
BnA C02Me Gentilucci, L.; Grijzen, Y.; Thijs, L.; Zwanenburg. B, Tetrahedron Lett., 1995, 36, 4665 OSiMQ
NHPh
, PhNH2, rt OMe
PhCHO
*
10% Yb(OTf)3 , MS 481, CH2C12
C02Me PhHN
90% . Kobavashl. S,; Araki, M.; Yasuda, M. Tetrahedron Lett., 1995, 36, 5773
M
N----h PhJ VS.;
m.
NHPh OMe
5% Yb(OTf)3, CHgl;? , O°C .
C
1995,
OSiMej
Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett, 1995, 233
4
CO2Me 9hv
N---H anthraquinone , MeCN
-C
NJco2Me
93%
S,; Kumar, J.S.D.; Shivaramayya, K.; George, M.V. J. Chem. Sot., Perkin Trans. I., 1797
Section 352
Amine - Ether
1% [~2OW41
309
9(3$Cl2
-
,,//“-‘”
COzMe
Ph-N
c MeO$XH=Nz Moran, M.; Bem~dinel~~ G.; Mtiller, P. Nelv. Chim. Acta, 1995, 78, 2048
Ph
N2CHC02Et, CH2Cf2
35%
Ph h P
&-b++-ph Cu(OTf), , -2S’C
.
(1.7 Rasmussen,KG.; Ph \ N r
PhQ N2CHC02Et, CUPF~(M~CN)~ g CH&
Ph
1) 80%
J. rhea. Sot. Chem. Cu~~~n., 1995, 1401
, bis-oxazoline ligand -b N / Ph
Ph+ 9+ + iw~~~ C02Et
+
C02Et
/ Ph
..
(4
1) 37% 35% ee
4‘4%iX
Hansen, K.B.; Finney, N.S.; &obsen. EN, Angew. Chem. Int. Ed. Engl., 1995, 34, 676 RelatedMethods:
Section315 (Carboxylic Acid - Amide) Section 316 (Carboxylic Acid - Amine) Section344 (Amide - Ester)
SECTION 352: AMINE - ETHER, EPOXIDE,
1, Dibal
-4
THIOETHER
OTBDMS
Ph t
+
‘* LiW 3. Hz0
H2
9) 43% ; Contento, M.; ~iacomini, D.; Mezzini E.; Giovagnoli, D. Tetruhed~u~~ 1993,49, 3809
(91
l
310
Compendiumof Organic Synthetic Methods, Vol9
PI -t-Bu
Section 352
/ t-Bu 1. PhSeBr, CH2CI2, O°C 2. NaBH4, MeOH
De Kimpe, N.; Boelens, M. J. Chem. Sm. Chem. Commun., 1993,9 16 hv (254 nm, Quartz), acetone 2h 88%
(48% conversion) Q~QL J,; Guha, M. tetrahedron Mt., 1994, 35, 1715
l.NaN3,ICl 2. LiAlH4 3. PhCOCl
Ot-Bu
li
4. NaI , acetone 5. NiO2
t-Bu ca. 30%
ca. 50%
Eastwood, F.W.; Perlmutter, P.; Yang, Q. Tetrahedron Lett., 1994, 35, 2039
OH
c(NHC02Et
PhSeCl , CH2C12 -78OC+ rt ,18h
* GILSePh I C02Et
(5
+
..
KSePh I CQ2Et 1) 61%
Cooper, M.A.; Ward. AD, ~~trahedrun Lett., 1994, 35, 5065
ci
NHiPr 1. NBS, (Bz0)2, CC14, heat
~
Cl
2. iPrNH;! , ether, Tic14 3. NaBH4, MeOH
Dc Kimpe. NI; Stanoeva,E. Synthesis, 1994, 695
52%
Section 353
Amine - Halide
AH Ph-
NHSiMe 3
J-G ld
Y,; Nishiyma, Jpn., 1994, 67, 879
O\ -c I
1. mt2
C8Hl
so2
0
*
Ph-*
OSiMe3 I H 84% K.; Zhang, K.; Okuda, F.; Kondo, T.; Tsuji, Y. Bull. Chem. SK. Co2(CO)g, CO (1 atm)
Wm.
311
, CHK12 (>90%) Et2N+ +‘“‘, )
PhOqwt2
2. PhOH , NaOH , THF C8h7
C8h7
61% 30% Richardson, P.F.; Nelson, L.T.J.; Shamless.K.B. Tetrahedron Lett., 1995, 36, 9241
17
0
hv , PhSH ,2h
fl
N
..
(82
6:12) 66%
trans:cis Naito. T,; Honda,Y.; Miyata, 0.; Ninomiya, I. J. Chem. Sot., Perkin Trans. l., 1995, 19
SECTION 353: AMINE - HALIDE, SULFONATE Br2, CH2C12 0.5 MeOH * 0.01 Et3NHCl
Brr-(=)-NMe2 near quant.
Gervat, S.; Lbnel, E.; Barraud,J-Y.; Ratovelomanana. V, Tetrahedron Lett., 1993, 34, 2115 “Ni;?B” , H20,15OC ,30 min 72% “Ni2B” = Ni(OAc)2.4 HzO/NaBHd Seltzman. H.H,; Berrang, B.D. Tetrahedron Lett., 1993, 34, 3083
312
Compendium of Organic Synthetic Methods, Vol9
Section 354
CF3SiMe3 , THF Etw, 15h,rt
Felix, C.P.; Khatimi, N.; Laurent.
Tetrahedron Lett., 1994, 35, 3303
mco2Et 0
iPrOH,HCl(+rt+ CN
I H
Foley. L.H, Tetrahedron Lett., 1994, 35, 5989
96%
SECTION 354: AMINE - KETONE
C Rechsteiner, B.; Texier-Boullet,
+ ON I
t
0
microwave (300W) 3 min
UPh
\ 0I /
, SiO2
N-H
F.; j-bnelin.
O- Li+
0 TfO-
-78OC
+
89%
J, Tetrahedron Lett., 1993, 34, 5071
/rHF
*
*35%
23OC
F . Kiselyov, A.S.; &&QWS~ I,, J. Org. Chem., 1993, 58, 4476
hv ,9,10-dicyanoanthracene
Zhang, X.; Jung, Y.S.; -0. 1993, 34, 5239
P.S.: Fox. MA;
78% Martin, P.S.; Merkert, J. Tetrahedron Lett.,
Section 354
Amine - Ketone
313
hv*
c
Winkler. JD,; Siegel, M.G. Tetrahedron Lett., 1993, 34, 7697
2
Me
\
hv ,9,10dicyanoanthracene MeOH/MeCN
,,o*,Me
M fd ,\\-\
Bn
N\
Bn 23% at 73% conversion
TM .
Khim, SK.; Marianr,. PLS, Tetrahedron Lett., 1994, 35, 999
0
0
0
O
PhNH;! , PhH , reflux
-*
*
0
0
0
N I Ph
90% Adembri. G,; Celli, A.M.; Lampariello, L.R.; Scotton, M.; Sega, A. Tetrahedron L&t., 1994, 35,4023
\ CT NH2
I
N
/
1. PhCHO 2. TMSOTf , MeCN acetophenone
*
&q-
N 43% Moutou, J.L.; Schmitt, M.; Wermuth, C.G.; Bourguignon, J.J. Tetrahedron L&t., 1994, 35, 6883 0 OMe Eu(fod)3
Degnan, A.P.; Kim, C.S.; Stout, C.W.; Kalivretenos.
* / N \ H 56% A.G, J. Org. Chem., 1995, 60, 7724 ti
Compendiumof Organic Synthetic Methods, Vu19
Section 354
hv,DCA,MeCN
less selective with pyrrolidine derivatives anti, 18% Hoegy, LE.; Mariano. P.S, Tetrahedron Mt., 1994, 35, 8319
Clark. JS,; Hodgson, P.B. .I. Chem. Sot. Chem. Commun., 1994, 2701
20% Bu&IReOd , CF$QH DCE , refiux ,2h
76%
Me0 Kusama, H.; Uchiyama, K.; Yamashita, Y.; Narasaka,K, Chem. Lett., 1995, 715
4 PhCHO
,OMe Me
, ArNH2, THF-H20
10% Yb(OTf)3 Ar = 4-chlorophenyl QbaWhi- St; Ishim& I-I. J. them. Sot. Chem. Co~un.,
1995, 1379
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
Amine - Alkene
Section 356
Ph , 10% NiBrz(PPh& 0 Id
Shida, N.; Kubota, Y.; Fukui, H.; Asao, N.; Kadoata,1.; 1995, 36, 5023
SECTION 355: AMINE - NITRILE SiMe3
f 3% BF3*OEt2, 0°C ,4h
..
(2.6
1) 84%
S.(z; Seth, P.P. Tetrahedron L&t., 1995, 36, 3793
SECTION 356: AMINE - ALKENE
HBn Bn.
\
H
N&; ~~poulou,
1. (CHZO)~,9O*c BnzmPh 2.
W)z~Ph
81%
9O*C, 30 min I. Tetrahedron Lett., 1993, 34, 583
1. set-BuLi , -78*C 2. MeI
t :: ;z2,
THF-SPA
IbSez, P.L.; JWera, C, Tetrahedron ktt., 1993, 34, 2003
Me
90 x 42%
316
Compendium of Organic Synthetic Methods, Vol9
Section 356
t-Bu t-Bu,
> THF , -78OC
Wegman, S.; Wiirthwein. E.U. Tetrahedron Lett., 1993, 34, 30;
0 N
PhCHO
M
+
cat. PdC12(PPh3)2 Me
\
K2C03
I (E+Z)
Ph in Toluene 10% 85% in DMF 72% 2% Filionini. L,; Gusmeroli, M.; Riva, R. Tetrahedron Lett., 1993, 34, 1643 0
OBu
1. LDA , -78°C THF + xylene
2. xylene , reflux ,4h b,tiHBu
moda.
+
&HBu
(99.5 : 0.5) 92% T,; Tats&i, S.; Shiraishi, Y.; Akasaka, M.; It& S. Tetrahedron L&t., 1993, 34, 3297 OMe OMe
1. BF3aEt2, 2. crc12
THF
3. ally1 bromide , rt P
4. 10% aq. Na2C03
Giammaruco, M.; Taddei. M,; Ulivi, P. Tetrahedron Lett., 1993, 34, 3635
65%
Section 356
Amine - AIkene
N3
317
EtO$Y@‘t-
1. PPh3
+
2
%@Et
l
C02Et
Et02
C02Et
am-
EtO$
Y
92%
0
Palacios.F,; Perezde Heredia, I.; RubiaIes,G. Tetrahedron Lett., 1993, 34,4377
. -K.;
.
Kaneko, M.; Yajima, T. Tetrahedron L&t., 1993, 34, 4841 h
Bu$nH , AIBN ,O.O5M (syringe pump) ,2h
NHPh
h +
*
pi
/
PA
Phvv
SePh
45%
23% Refvik, M.D. Tetrahedron Lett., 1993, 34,490l
Schvvan.;
Me$\ (CH20)n, p-tsOHaH20 MeCN ,6Q*C
67-69% (64-67%ee) 4’J4Hb,,*,
Bn\
-
$
Bn
H Castro, P.; Ovem
J&;
Zhang, X.; &briano, P.S, Tetrahedron Lett., 1993, 34, 5243 t-BuNH2, MS 3A, 2h CH2C12,22*C
*
P
Merrr,,, t-B
94%
Sigman, M.S.; Eaton. B.E, Tetrahedron Lett., 1993, 34, 5367
t-Bu H
318
Compendium of Organic Synthetic Methods, Vol9
Section 356
Pb
l.LDA.THF
78% de1 Pozo Losada, C.; Olano, B. Tetrahedron Lett., 1993,34, 5497
Barluenu;
Bi/BuflBr
, MeCN
PON-Pb -Br
Bbuyan, P.J.; Prajapati, D.; Sandhu, JS, Tetrahedron Lett., 1993, 34, 7975
N Cb
, toluene , bv I
2
CH20Et
2.23OC, 12b 3. TBAF
N
\
N c
d N \ CH20Et
91%
Knapp. S,; Albaneze, J.; Schwar, H.J,J. Org. Chem., 1993, 58, 997
(66
..
34)
I Bn
Pb
Bebolz, L.G.; Stille, J,R, J. Org. Chem., 1993, 58, 5095 Phi , Pd(PPh& K2CO3 DMF , 70°C NHBn Davies, I.W.; Scopes, D.I.C.; Gallagher, T. Synlett, 1993, 85
99%
Section 356
Amine - Alkene
319
SnBu3 Bn\
.I
;;IJJTY
yHBn+
p-Me
. (17 Coldham. I, J. Chem. Sot., Perkin Trans. I., 1993, 1275
83) 65%
l
Leurs, S.; Vanderbulcke-Coyette,B.; Viehe, H.G. Bull. Sot. Chim. Be&., 1993, 102, 645
V9:nzBr3
NHPh
DMF
*
PhL
Jin, S.-J.; Araki, S.; Butsunan. Y. Bull. Chem. Sot. Jpn., 1993, 66, 1528
N
/
SEt
Bn A
w H
AlC13, CH&
, rt
voms NHBn
OTBS
84%
SEt
\r 77% Tohyama, Y.; Tanino, K.; Kuwajima. I, J. Org. Chem., 1994, 59, 518 I
4 w
NHTs
Br ’
5% Pd(OAc);!
N 10%P(o-Tol)3 , Na2CQ I -Ko Ts 88% 2 Bu@Cl ,9O”C, Id Larock. RC,; Yang, H.; Weinreb. S.M,; Herr, R.J. J. Org. Chem., 1994, 59, 4172
320
Com~n~um
of Organic Synthetic Methods, Vo19
Bernard-Henriet, C.; Grimaldi, J.R.; Hatem.
Section 356
NHNMe2 89% Tetrahedron Mt., 1994, 35, 3699
N I
..
(2.7 pearsOn. W&;
Me 1) 65%
1
Jacobs, V.A. Tetrahedron Lett., 1994, 35, 7001 PhNHOl-l , FeC12/FeC13 72% *
Srivastava, R.S.; Nicholas,.M.
w
NHPh
tetrahedron Lett., 1994, 35, 8739
dco2t-Bu
L
C7Hl
LDA Ahman, J.; &&&j.
P,J, Am. Chem. Sot., 1994, 116, 9781
Ph-NW
1. Ni(cod);! , MeCN Br
45% 2.16 NaBH4,6 MeOH
Sol& D.; Cancho, Y.; Llebaria, A.; Moret6, J.M.; Del&ado. A, J. Am. Chem. Sot., 1994, 116, 12133
Amine - Alkene
Section 356
321
1% (PCy3)g12Ru=CHCH=CPh2 wPhH , eflux ,6h a &I 86%
‘\OAc Kinoshita, A.; Mori. Synlett, 1994, 1020
\ - OAc -
-C-JO Fisher. GB,; Lee, L.; Klettke, F.W. Synth. Commun., 1994, 24, 1541 Ph Zn(Cu) , MeOH, H20, rt
\ /N\e . m.
Br
ultrasound
&, Jolie, R.; De Smaele,D. J. Chem. SE Chem. Cajun.,
1994,
53% 1221
Ph C02t-Bu
fN
/
LDA , TI-F , -78OC -n-
T
N I H
C02t-Bu
63% Coldham. I.; Collis, A.J.; MouId, R.J.; Rathmell, R.E. Tetrahedron Lett., 1995, 36, 3557
1
Et2N HNEt2, 20% Et3NHI, THF 10%Pd(dba)z,2 PPh3 65OC,
c7-h
b
18h
+
C7Ht
i J 70% (96:4 E.-z)
Besson,L.; Go&, J.; Gazes.
Tetrahedron Lett., 1995, 36, 3857
322
Compendiumof Organic Synthetic Methods, Vol9
Section 356
C@Me Tf
4
NaCH(C02Me)2,5% Pd(PPh& LiCl , DMSO , 60°C
\
C02Me *
N Bn’
Vieart, N.: Gazes,B.; m C3H7
N
jBn
A v
53%
Bn’ Tetra~dron
Lett., 1995, 36, 50 15
ether, -5OOC-+ -1OOC,4h
Ph
*
F== C3H7
Ph
Ph
Proi/Ti
OiPr
Gao, Y.; Harada,K.; Usato, F. Tetrahedron Lett., 1995, 36, 5913 Ph Bu+i’--@ *
phi
15% Yb(OTf), , CH$12, rt N\ HN\ Ph Ph Bellucci, C.; Cozzi, P.G&;Umani-Ronchi, A, Tetrahedron Lett., 1995, 36, 7289 1. ~~~~~~ ph-NPh
NHPh
, Me$iCl
2. aq.NH@ 96%
Wang, D.-K.; Dai. L.-X.: Hou. X.-L, Tetrahedron L&t., 1995, 36, 8649 Ph2P
Ph2P
b
\I
Ph w--h3
w-h3
(8
cc;&3 l .
1) 80%
(5:1 cis: tranws)
Didiuk, M.T.; Morken, J.P.; fioveysla. A& J. Am. Chem. Sot., 1995, I1 7, 7273
56%
Ester- Ester
Section 357
323
13F3*OEt2, 210°C ,2h w
Br Ph~
5 eq m~~huline , lOO*C 10 eq. H20, 2d
SECTION 357: ESTER - ESTER
~~~~H f AIBN , TuI reflux ,2h
*
0 Ph ; Kee, I.S. Te?~~~e~~~~Lett., 1993, 34,4213
2. Hfl 3. p-TsOH , toluene
Shimada, S.; Tohno, I.; Hashimoto, Y.;
*. 8) 85~ (92 Chem. Lett., 1993, 1117
324
Section 357
Compendium of Organic Synthetic Methods, Vol9
r
l/50 CoC12 ,42h *
r
OH
OCHO
DME , 02, 80°C
Li, P.; Alter.
H, Can. J. Chem., 1993, 0 C02Me
K
acetone, SmI2 , THF 4% Fe(dbm)3 , reflux
C02Me 74%
CO2Me
-b Imamoto. T,; Hatajima, T.; Yoshizawa, T. Tetrahedron L&t., 1994, 3.5, 7805 Mf30
OTMS
I Pd(PPh3)4, TlOAc OMe , HF reflux , Id 89% T,; Kondo, Y.; Masumoto, K.; Yamanaka, H. J. Chem. Sot., Perkin Trans. l.,
aoto. 1994,235
0
PhCHO , Cp2Sn(thf)2 0-
To1 , O°C + 25OC
-
A(&()‘ph
Takano, M.; Kikuchi, S.; Morita, K.; Nishiyama, Y .; m.
77% Y. J. Org. Chem., 1995, 60, 4974
NaB0~4 H@ , Ac20, PhH Ph Nag03,55OC,
14h 67%
Bhat, S.; Ramesha, A.R.; Chandrasekaran. S, Synlett, 1995, 329 Also via Dicarboxylic Acids: Hydroxy-esters Diols
Section 312 (Carboxylic Acids - Carboxylic Acids) Section 327 (Alcohol - Ester) Section 323 (Alcohol - Alcohol)
325
Ester- Ether
section 358
SECTION 358: ESTER - ETHER, EPOXIDE, THIOETHER Bu$W-I , AIBN sPhH reflux ,6h, syringe asp t
Lee.;
Br Tae, J.S.; Lee, C.; Park, CM, T~tra~dr~n Lett., 1993, 34,4831 Me3
A
P
OH
@Me
1. CsF , M&N 2,
Meo2 k
92%
C02Me
Hojo, M.; Ohkuma, M.; Ishibashi, N.;
Tetrahedron Lett., 1993, 34, 5943 OTMS
0
(Tf~)2Sn(bis~~ine) w CH2C12,9h , -78OC
Ph
EtS I
PhCHO
86~ (93:7 ~~n:a~ti)
Kobayashi, S.; IJchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron, 1993, 49, 1761 OzEt
1.3Bu$nH 0.25 AIBN C.X&Et 0.03M PhH reflux ,8h
54) 91% (46 ; Tae, J.S.; Chong, Y.H.; Park, Y.C.; Yun, M.; Kim, S. T~tra~~dr~n Let& 1994, 35, l
129
CCHO
ems ===c,40% sno SEt
*
20% Sn(OTf);! chiral diarnine slow addi~ou (3h) ; Kawasuji, T.; Mori, N. Chem. Let& 1994,217
SEt 61% (62% ee)
326
Section 359
Compendium of Organic Synthetic Methods, Vol9
COZMe Rhz(OA& , MeOH
49% Tet~a~d~~~ Lett., 1994, 35,
Cox, C.G.; Haigh, D.; Hind~~y, R.M.; Miller, D.J.; 3139
0 CP \ “_/“e
1. PhCHO , ZnC12 , CH2C12 , rt 2. CAN, MeOH, -78OC, CO
= Me0 Ph
oc T~trahed~~~ Lett., 1994, 35, 7889
Jiang, S.;
~cl2-AgPF6, MeO$
COzMe
CH$&
CO,n/le
=
MeOH
*
MeO$Z
f==c
C02Me
quant. Kataoka, Y.; Ma~umot~, 0.; Ohashi, M.; Yamagata, T.; Tani. K, Chem Lett., 1994, 1283
SECTION 359: ESTER - HALIDE, SULFONATE [CF2Br$Z#n, DMF ,2h, rt] HMPA , CuBr , 60°C, 40 min *
98% 0
0 Mawson, S.D.; Weavers. R,T, Tetrahedron Let& 1993, 34, 3139
HoqoH
3HBb~~,lhh_
Bc
= S
= r:
=: =
= =
$H
&H
XAc
XAC
2.2 MeCOBr , dioxane ) 16h
/
80% El Anzi, A.; Benazza, M.; Frechou, C,; Demaillv, C, Tetrahedron Lett., 1993, 34, 3741
Br
Ekter- Halide
Section 359
327
s
CHzC12,18h m-
cCO2H
his-(sym-collidine) iodine(I) hex~~ophosphate Simonot, B.; Rousseau G, J. Org. Chem.,1993, 58,4
76% I
89%
Kitagawa, 0.; Inoue, T.; Hirano, K.; muchi.
T, J. Org. Cbem.,1993, 58, 3106
IQ, sodium persulfate, NaHC03 HOD Royer, AC.; Mebane, R.C.; Swafford, A.M. SynZett, 1993, 899
0
BzCl ,0.4 SmI3, MeCN , rt t
BzO/-\I
0
Yu, Y.; m.
87% Y,; Ling, R. Synth. Commun., 1993, 23, 1973
*c
I
1. HC=CC02H, NC1 , CH2C12 2. (BzO), , PhH, eflux
Haaima,G.; Lunch, M.-J.; Routledge,A.; Wu
0
78~44%
0
Tetrahedron, 1993,49,4229
ICH2C@Et, DMSO BEt3, rt (opento air)
C02Et -
T
; Mu~gl~, E. Tetr~~~~r~~ Left., 1994, 35, 2763
I
54%
328
Compendiumof Organic Synthetic Methods, Vol9
BQ\ #
y-CO2H
H
1. mcpba
Section 359
ONlb2
2.12, NaHC03 50%
Reetz. MT,; Lauterbach,E.H. Heterocycles, 1993, 35, 627 Me
b.
X,; Wang, 2.; Ji, J. Tetrahedron Lett., 1994, 35, 613
Mimero, P.; Saluzzo, C.; m.
R, Tetrahedron Lett., 1996, 35, 1553
BeIIesia, F.; Boni, M.; Ghelfi. F,; Pagnoni, U.M. Tetrahedron L&t., 1994, 35, 2961 FzBr
Bu$nH , AIBN, PhH
t reflux , l-15 h addition ~ Meat ButtIe, L.A.; Motherwell. W.B, Tetrahedron Lett., 1994, 35, 3995 MeOg
Section 359
Ester - Halide
329
0 A Buoys
ma
c1
TBAB 190°C ) 6h S 97% K~ey~~
A.; Kiyota, M.;
Ph Y
0
T~tr~~~drun L&t., 1994, 35, 4571 Cl
AcCI , Cp2YCI w CH2C12, 13h
AcO ~
Ph
..
(88 ; Zhu, I), ~ynt~. ~~~~~.~
Cl
+
AC
Ph 12) 95%
1994, 24, 2203
I2 , Pb(OAc)za3 Hz0 , AcOH wrt ,6h 85% Bedekar, A.V.; Nair, K.B.; S~rn~n. R, ~ynt~. ~u~~~n., 1994,24, 2299 Br
PhMe3Nf Brf Ir Br
; G&in, R.H.; Musket,
GM.; Aionso, M.S. Tetr~~edrun, 1994, 50, 6433
Cl
Pimmg, F.O.H.; 1994,50, 12415
0.3 Cu(~py)C~ , DCE
57% (70:30) ; Kaptein, B.; Schoemaker, H.E. Tet~~~dr~~~
Compendiumof Organic Synthetic Methods, Vol9
330
00
, Zn , ether
0 w
25OC, 18h
Cl
Section 360
PhK
,/\/\/c’ 70%
Bhar, S.; &nu. BC, J. Org. Chem., 1995, 60, 745 SECTION
360: ESTER - KETONE 0 55%
1. Br
OH
Ktr
Br Py, ether Cd-f23 53% 2. TMSCl , ether cl lH23 Zn , reflux Landi Jr., J.J.; Garafalo, L.M.; &.mig. K, Tetrahedron Lett., 1993, 34, 277 COzMe
2% Rh2[02CCH(Bn)NPhth]4 C02Me
CO2Me CH2C12,O°C
d-
3S S bh
96%
(46%ee, R) Hashimoto, S.; Watanabe,N.; Sato,T.; Shiro, M.; Ikegami. S, Tetrahedron Lett., 1993, 34,
5109
x
Ph
1.7 PhI(OH)OTs , CDC13
-A rt ,2h 98% CO2Et C02Et Barton, D.H.R.: Jaszberenyi.J.Cs,; Shinada,T. Tetrahedron Lett., 1993, 34, 7191 PhCHO , EtN02 AlC13, 100°C, 5h
Sartori. (i; Bigi, E.; Maggi, R.; Bemardi, G.L. Tetrahedron Lett., 1993, 34, 7339
331
Ester - Ketone
section 360
Br
PhL
l-
, csgo3,
CH$& C02Et
48h, 30°C 2. aq. HCI, CHCI3 , Him-da, Y.; unhip,;
Tanaka, Y,; Ueda, I. J. Org. ~~~.,
1994, 59, 111
1. (Coa)2 , hv t
60%
2. MeOI-I
02Me ; Hardee, J.R.; Gelber, N.; Qi, L.; Axenmd, T. J. Org. Cbem., 1994, 59, 2131
ICI-I ) THF ,18-c-6 , rt
Me
4
60%
0
AC
Ph JL
OAc ,4% Pd(P~h3)2C12
Cl
w C7Hl K
SnBu3
Ph C7Hl
8% CuCN ,75”C, 18h
~
J, Am. Cam. Sot., 1994, 116, 1
Ye, J.; Bhatt, R.K.;
N c1
Ph -If
0
CO&B u
0
0
IsJr&o. B, Te&hedron
96%
L&t., 1994, 35, 5073
74%
0
332
Section 360
Compendium of Organic Synthetic Methods, Vol9
Me
Me
Mn(OAc), , AcOH 8O”C, 8h w
Me02C
0
C02Me 57%
C.-P,; Wang, S.-F. Tetrahedron Lett., 1994, 35, 4365 1, NaH , DME ,40°C 2. BuLi 3. PCC , Al203 , CHg12 93x68x68% Piers. E,; Cook, K.L.; Rogers, C. Tetrahedron Lett., 1994, 35, 8573 0 KMn04, CuSO&
Hz0 47%
4h * Das, J.; w
0
c
0
S, Tetrahedron, 1994, 50, 11709 e- , CH2C12- Hz0 NaBBr2
C02Me
C02Me 87%
Maekawa, H.; Ishino, Y.; mguchi. OH PhI-
L Chem. L&t., 1994, 1017
aq. t-B&OH, C02Et
1% CuC12,3% TBAB
CH2C12, 25OC, Id
*
PhA
C02Et 96%
Feldberg, L.; Sasson. Y, J. Chem. Sot. Chem. Commun., 1994, 1807
Section 360
Ester=Ketone
333
68% Ryu, 1; Nagahara,I(.; Yamazdci, H.; Tsunoi, S.; Sonoda. N, Synlett, 1994, 643
Bu$nH, AIBN
(9
m,
Kinter, KS. J. Org. Chem.,1995, 60, 4850 OCQMe
Barba, I?.-
e’ , DMF/LiCIOd
0
67% h&G.: Montero. Cr..I. Org. Chem.,1995, 60, 5658 KMn04, pH 7 OEt
Tat‘iock. J,& J. org. Ckm, 1995,
C02t-B u
60,
OEt 0 97%
6221
1. CuBr2, PhI(OH)OTs , 0°C 2. DMAP .,dimethyldioxirane CH2C12,O”C
0 C@t-Bu 0
1st stepis quant Coats, S.J.; Wasserman.H.H, Tetrahedron Lett., 1995, 36, 7735
OPh
1.
J-I-IF
Li
PhCHO w;
Section 361
Com~n~um of Organic Synthetic Means, VoI 9
334
oAc
88~78%
2. p-TSA , A&H, 90°C , ld * PhA/ Yang, 2.; Moutou, J.-L. Tetrahedron Lett., 1995, 36, 841
l
--c Br
0
SmI2, THF , -35*C, 5 min
0
4 0
0
72%
d Park, H.S.; Lee, I.S.; I(im. YK
Tetrahedron Lett., 1995, 36, 1673
REVIEW:
“Alternate PreparationsOf aXeto EstersFrom Acid Chlorides,” &&i&&y. A,&; Wang, 2.; Wells, A.P. Org. Prep. Proceed. Int., 1995, 27, 457 AIso via ISetoacids Hydroxyketones
Section320 (Carboxylic Acid - Ketone) Section330 (Alcohol - Ketone)
SECTION 361: ESTER - NITRILE OAc I phwCHO
Nc Pdz(dba)&HQ , dppe MeCN, Id
Nemoto, H.; Kubota, Y.; Yamamoto. Y cJ. Chem. Sot. Chem. Commun., 1994, 1665
TBAF,THF,lh LiCI , rt
94% CN
Stojanova, D.S.; Milenkov, B.; Hesse.M, Helv. Chim. Acta, 1993, 76, 2303
Ester- Alkene
Section 362
335
ESTER - ALKENE
SECTION 362:
This sectioncontains synthesesof enol estersand estersof unsaturatedacidsas well asester moleculesbearing a remotealkenyl unit. 0
C02H
1. Br2, NaHC03 2. AgNOj , AcOH
Bu
Bu 66x50%
J&,&
T&; Huang, J. Tetrahedron Lett., 1993, 34, 1411 1. &CO3 ,5 kbar 2.5% Pd(OAc)z , 10% P(2-furyl)3
Jco2H
61%
3. HC=CCMe20Ac, DMSO 20°C , 14h ** Bouyssi, D.; Gore, J.; BaIme, G.; Louis, D.; Wallach, J. Tetrahedron L&t., 1993, 34, 3129 Me
90% Ciattini, P.G.; Mastropietro, G.; Morera, E.; Ortar, G, Tetrahedron Lett., 1993, 34, 3763
Ph-C=CH , NEt3, MeCN , rt 0 PdC12(PPh3)2 , CuI , 1Oh
*
Cu. X,; Huang, X.; Ma, S. Tetrahedron Lett., 1993, 34, 5963
Me$iCH=C=O , PhH OSiMe3
reflux ,3d
Me$iO Ito, T.; WT...
.
. ..
Me& T, Tetrahedron Lett., 1993, 34, 6583
P Ph
80% (>97:3 z:E)
336
Compendium of Organic Synthetic Methods, Vol9
\a
C@Me
Section 362
PBn C@Me
I
MeN02, 80°C
0
65%
A
OBn
&lark& I.&; Evans, G.R. Tetrahedron tett., 1993, 34, 7309
c
Co-Cl2 C@Me
(30
Me0 Et
..
70) 29% [60:40 E:zJ
Bhatia, B.; Reddy, M.M.; Iabal.
@Et
Tetrahedron L&t., 1993, 34,630l
1. SnC12 / 2.
=c_ ut.
CI-IO ,ether,rt >
F,; Gabriel, A.; Maillard, B.; Pereyre, M. Tetrahedron Lett., 1993, 34, 7749 cw
w bock.
5% Pd(OAc)z ,2 NaOAc DMSO , O2 )
am0
86%
RC,; Hightower, T.R. J. Org. Chem., 1993, 58, 5298 Bn
AcHN -A
1. PhSeCH$H20H, cw
Weinhouse, ML; Janda.
EDC
DMAP , DMF 2. Hz@, THF 3. iPr$H , CHCl3, reflux Synthesis, 1993, 8 1
Bn w AcHN
A
04 92x90%
Section 362
Ester - Alkene
337
+h\
cCO2H
DMSO , Na2CO3 28-46h
70% Tetrahedron L&t., 1993, 34, 8545
Annby. U,; Stenkula, M.; -C.-M.
30%
;Jmco2Et
PPh3 7PhH , rt ,8h
Guo, C.; Lu.
.I. Chem. Sot. Chem. Commun., 1993, 394 Et0
OMe
CO2Me
,O.S Bu$nH E tog-
41% doMe
Lee. E,; Hur, CU.; I&e, 1466
,0.05 AIBN , reflux ,4h PhH (0.01 M) , syringe* pump v(2h)
C02Me Y.H.; Park, Y.C.; Kim, S.Y. .I. Chem. Sot. Chem. Commun., 1993,
P(OEt)3 , NEtyH20
,120OC -
C02Et
-COzEt
8h (sealed tube) 96%
Hirao. T,; Hiraw
K.; Ohshiro. Y, Bull. Chem.
TIN,
SOC.
Jpn., 1993, 66, 2781
MeOH,3MHCl 3-26h
Me0 Me0 Thakkar, K.; Cushman, M, Tetrahedron Lett., 1994, 35,644l
Section 362
Compendiumof Organic Synthetic Methods, Vol9
338
Pd(OAc)z , dppp , PhMe , MeOH w COzMe reflux
Mand;u. TJ Tsujiguchi, Y.; Tsuji, J.; Saito, S. Tetrahedron Lett., 1994, 35, 5701 Bu [Pd(MeCN)2(p&)d @=I12 co, THE;, 5o”c (10 Kg cms2)
‘b O
0
+Bux; 2
.
83) 92% Y, Tetrahedron Lett., ;994, 35, 5889
(17
Matsushita, K.; Komori, T.; Oi, S.; w.
l.NaI-I,TMEDA,THF,reflux 2. inverse addition to PhOCOCl
0a
OPh 43%
Harwood, L.M.; Houminer, Y.; Manage, A.; Seeman.J-1,Tetrahedron Lett., 1994, 35, 8027
eC02Me PhCHO
*
phL-oH
34%
DABCO , microwave, 10 min CO2Me Kundu, M.K.; Mulcherjee, S.B.; Balu, N.; Padmakumar,R.; I$&& S.V,Synlett, 1994,444 BrCHzCOfle , Bu3As , 10% Cd PhCHO
100°C ,20h
Zheng, J.; ahen, Y, Synth. Commun., 1994, 24, 2069
*
PhwC02Me 87% (E only)
Nz
\)I
339
Ester - Alkene
Section 362
Lf Rh2(s-TBSP)4
CO2Me
p-(t-butyl)phenylsulfonyl prolinate 76% (63% ee) . TBSP = Peng, ava; Z-Q.; Houser, J.H. Tetrahedron Lett., 1994, 35, 8939 Mac
,3.5% Pd(OAc)z 8% PPh3 , 1.2 Ag2CQ , MeCN 90°C, 45 min 80%
Meyer, F.E.; Ang, K.H.; Stenig, A.G.; de Meijere, A. Synlett, 1994, 191 -0Ac
, CO, THF , autoclave
RuC12(PPh3)3-K2C03, 2OOOC, 77%
Kondo, T.; Kodoi, K.; Mitsudo, T.-u.; Watanabe.Y t J. Chem. Sot. Chem. Comnun., 1994, 755
1. Rieke Mg* , THF , rt 2. ethylene oxide ) THF , -78OC v
a
3.co;!,o”c + rt 4. H30+, 1lOC
Rieke. R.D; Sell, MS.; Xiong, H. J. Org. Chem., 1995, 60, 5143 Me0
nBu3 SPh
cu(No3)2
Ph
9m 9fi
CO2Me 65%
-
TV
CO2Me SPh Beddoes,R.L.; Cheeseright,T.; Wang, J.; Quayle. P, Tetrahedron Lett., 1995, 36, 283
340
Compendiumof Organic Synthetic Methods,Vo19
Section 362
COzMe Ph3A
CO2Me
4
SePh
PhCHO
*
CHC13,4h Huang, Z.-Z.; Huane,
4
SePh Y. -7* Tetrahedron Lett., 1995, 36,425
.
-F C3H7
96% (90:10, Z-E)
PhH
w7
Ph
I
5% ClzPd(PPh3h.4 NEt3 20atmC0,PhH,l10°C,10h
0
99%
Cop&et, C.; Sugihara, T.; Wu, G.; Shimoyama,I.; Negishi. E, J. Am. Chem. Sot., 1995, 117, 3422 -cl
; NEI+;IH2C12,-20°C
a *
.
0
w.
.
OBn 75%
G,; De Simone, A.; Mingardi, A.; Tomasini, C. Synlett, 1995, 1131
3) 95%
(>97
Zhu, G.; Lu. X, Tetrahedron Asymmetry, 1995, 6, 345 m PhO
Cl
SiMe3 , toluene AlC13, 20°C ,2h
-
PhOL 82%
Mayr. H,; Gabriel, A.O.; Schumacher,R. Liebigs Ann. Chem., 1995, 1583
Section 363
osMe3
OPl
. m.
341
Ether - Ether
M+C
-
COzMe
zrC14,Cc4,0°c
~
pflzc
+ rt
Mew . &, Sudoh, T.; Koyama, K. Bull. Chem. Sot. J’n., 1995,68, 1683 RelatedMethods: Also via Acetylenic Esters: Alkenyl Acids: P-Hydroxy-esters:
SECTION 363:
80%
Section60A (Protectionof Aldehydes). Section 180A (Protectionof Ketones). Section 306 (Alkyne - Ester). Section322 (Carboxylic Acid - Alkene). Section 327 (Alcohol - Ester).
ETHER, EPOXIDE, THIOETHER EPOXIDE, THIOETHER
- ETHER,
SeeSection60A (Protectionof Aldehydes)and Section 180A (Protectionof Ketones)for reactionsinvolving formation of Acetalsand Ketals. 1. DDQ , MeOH , CH2C12 rt, Id 2. aq. NaHC03 OMe &I. Y.-C,; Lebeau,E.; Gillard, J.W.; Attardo, G. Tetrahedron L&t., 1993, 34, 3841
4 /
H
iPrOH ,20% CuC12 5% Pd(N0)2C1(MeCN)2 2h
50% isolated Meulemans,T.M.; Kiers, N.H.; FeringZLR.L; van Leeuwen, P.W.N.M. Tetrahedron L&t., 1994, 35, 455
HO
DEAD, PPh3, CHg12, O°C HO OH
80% @-only) Sobti, A.; Sulikowski. G.A, Tetrahedron L&t., 1994, 35, 3661
78%
Section 364
Compendiumof Organic Synthetic Methods, Vol9
342
(a$ = 1:15) 81% BTIB = his-(trifluoroacetoxy)idobenzene Sun, L.; Li, P.; Zhao. K, Tetrahedron Lett., 1994, 35, 7147 TMS-SPh , DMF w
‘OMe ;w”l
Miura, T.; w.
0
87%
Y, Tetrahedron Lett., 1994, 35, 7961 OSiMqt-Bu Q = 2 s\
OMe
t
ZnI2 , THF
p-To1
70% (>99% e) Kita. Y,; Shibata, N.; Fukui, S.; Fujita, S. Tetrahedron Lett., 1994, 3.5, 9733
ETHER, EPOXIDE, THIOETHER SULFONATE
SECTION 364:
1. ClCH21, MeLi , -78°C ‘Ls 2. -78OC +
+20°c
Br Barluenu;
- HALIDE,
Me4N*#,,,, ,,\+,Me 62% $
Cl
Llavona, L.; Bemad, P.L.; Concellbn, J.M. Tetrahedron Lett., 1993, 34, 3173 H
XeF2
, CH2C12,35OC
Stavber, S.; Zupan, M. Tetrahedron Lett., 1993, 34,4355
Section 364
Ether - Halide
343
MnO2, AcCl w Cl 82% Bellesia, F.; Ghelfi, F.; Pagnoni, U.M.; Pinetti. A, GQzz.Chim. Ital., 1993, 123, 289
t(
OMe
OMe
Br2, Me&Cl, NaBr ,30 min B *
OMe
3-(
OMe 98%
Bell&a, F.; Boni, M.; Ghelfi.;
Pagnoni, U.M. Gazz. Chim. Ital., 1993, 123, 629
60% Antonioletti, R.; Magnanti, S.; Screttri, A. Tetrahedron Lett., 1994, 35, 2619 l.LDA,HMPA 2. acetone 3. X2,NaHC03
32x47% Galatsis. P,; Parks,D.J. Tetrahedron L&t., 1994, 35, 6611 H ,,OH @9
,,\\I”\l\
12, NaHC03 , dry MeCN
IIIIIIIIB u
Bu 16h 04
*
d-J
r,e % -1
75% Barks, J.M.; Knight. D.W,; Weingarten, G.G. J. Chem. Sot. Chem. Commun., 1994, 719 PhI(&~F3)2
9t t 12 cc14
D’Auria, M.; Mauriello, G. Tetrahedron Lett., 1995, 36,4883
83% I
Section 365
Compendiumof Organic Synthetic Methods, Vol9
344
AK13 , Id
.
(4 s
1) 60%
J.0,; Biermann, U. Bull. Sot. Chim. Be&., 1994, 10, 393
CT I
(collidine)$ PFi t
\A/\/\
0
CH2Cl2
95%
Brunel, Y .; Rousseau,G. Synlett, 1995, 323
&
12, CAN, MeOH *
rt ,2h
I*
+
I
.
I\
1) 88% (2 6 ; Hosokawa,H.; Kanamori, M.; Muramatsu, Y.; bhiai, K.; Takahashi,E. Chem. Lett., 1995, 13 .
.
SECTION
365:
ETHER,
EPOXIDE,
THIOETHER
- KETONE Me
‘OSiMe3
0
OH
BFpOEt2, MeN02, -25OC 30 min
?Y-
51%
(7:3 syn:anti)
Duhamel. P,; Guillemont, J.; Poirier, J.-M. Tetrahedron Lett., 1993, 34, 4197 2% Cu(hfacac)z, CH2C12 40%
reflux *
c
hfacac = hexafluoroacetyl acetonate Clark. J.S; Krowiak, S.A.; Street,L.J. Tetrahedron Lett., 1993, 34,4385
\
Section 365
Ether - Ketone
345
%
M
2Me:3Me) I
I 0
M&, Rivera-Fortin, M.A.; Byrne, N.E. Tetrahedron Lett., 1993, 34, 3505 Ph, t-Bu
, Me2AICl
A-
,,,,,d Ph
SPh
CH2C12,-45OC
(96:4) where 4 = other isomers Horiguchi, Y.; Suehiro, I.; Sasaki,A.; Kuwaiima, I, Tetrahedron Lett., 1993, 34, 6077 Me Me
TMS zc
I cf
5% TMSN(S02F)2 CH2C12,-78OC
Trehan, A.; Vij, A.; Walia, M.; Kaur, G.; Veu.. 7335
0
p-TsOH , H20, CH& 20°C, 12h Cossy. J,; Furet, N. Tetrahedron Lett., 1993, 34, 7755
&r
. Treh;iB. S, Tetrahedron Lett., 1993, 34,
*
SePh 70%
346
Section 365
Compendiumof Organic Synthetic Methods, Vol9
5
[mCl(C2H4)d
2 9 SnC12
acetone, Ar , 80°C
P
sealedtube, 1Oh
-* Tetrahedron Let?., 1993, 34, 7971
Ipatkin, V.V.; Kovalev, I.P.; Ignatenko, A.V.; Nikishin.,
C02Me TrSbC16,CH$12 ,-78’C (>2OO:1)
76%
Colander. GA; Cameron,K.O. J. Org. Chem., 1993, 58, 5931
M%* ,,+ (‘I
Al(OC&)3 , toluene O°C,2h
0
) o2
%
Me Ishihm, K.; Han&i, N.; Yamamoto, H. Synlett, 1993, 127 w-h1
0
= Z = Z
Me
Me
Me
>99% (86:14 S:R)
63% Groth, U,; Huhn, T.; Richter, N. Liebigs Ann. Chem., 1993, 49 OH MeCHO , PhSH , CH-& SiO2 , rt Fuchs, K.; m.
I&
J. Org. Chem., 1994, 59, 528
SPh
Section 365
Ether - Ketone
347
OEt C5Hdy 66%
O
PCWP = peroxotungstophosphate Sakaguchi,S.; Watase,S.; Katayama,Y.; Sakata,Y.; Nishiyama, Y.; I&ii. Y c.I. Org. Chem., 1994, 59, 5681 N-NHCO$t
7/
Me
1. Br2 3. 2. MeOH, NaHC03H+ 4. H30+
*
+
0
5. DBU 77%
Feuerer, A.; Sevea T, J. Org. Chem., 1994, 59, 6026 Ph k== TMSO
3 eq. SnC4, -78OC,CH$l;! *
PhbSPh
67% m.
k; Michael, J.P.; Walter, D.S. Tetrahedron Let&, 1994, 35, 5481 (~-To~)~S~, cat. Ph2CO , Yb rt ,3h
. . Tanlguchl. Y,; Maruo, M.; mi.
STolyl IL; Fuiiwara. Y, Tetrahedron Lett., 1994, 35, 7789
KF-Al203 , t-B&OH, Pha ~v.K.;
Ph
0 CH2C12
MeCN , 10 min
Ph
5, PhI>K 0
quant
Kapoor, K.K. Tetrahedron Lett., 1994, 35,948l 0
1. NBS, (BzO)2, CC4, heat 56% +
2.1.5 Ag2C03 , MeOH , heat
Me0 . Cl m. N,; Stanoeva,E.; Boeykens,M. Synthesis, 1994,427
OMe
Compendiumof Organic Synthetic Methods, Vo19
348
Section 365
1. EtCH(OMe)z , TiCL4 ;~lz,-780C,lh
EtzNqms2
.
2
quant. 0 Hojo, M.; Nagoyoshi, M.; Fujii, A.; Yanagi, T.; Ishibashi, N.; Miura, K.; Hosomi. A, Own. Lett., 1994, 719
OH
W-h
2
4
OAc
9 CH2Cl2
2 snCl;!,2 NCS , -1O’C 80% (40x50synxznti) Masuyama. Y,; Kobayashi, Y.; Kurusu, Y. J. Chem. Sot. Chem. Commun., 1994, 1123
4f
CO2Me
3e4*
>
C02Me
Ph
25OC, lh
PPh3
Ph %
0 quant.
asserman.H.H,; BaIdino, CM.; Coats, S.J. J. Org. Chem., 1995, 60, 8231
N&O3
9 (C@&tN
HS04
CH2C12,rt ,2h aub. TS, Tetruhedron Lett., 1995, 36, 663
Phi , 10% Pd(PPh& , DMF K2CO3, 60°C ,18h
Ph
(23:77 cis:trans)
Walkun. R.D,; Guan, L.; Kim, Y.S.; Kim, S.W. Tetrahedron Lett., 1995, 36, 3805
Section 365
Ether - Ketone
349
PhI(OAc), , Mg(C10d2, rt CWQ--IOH 9I-W 9pH 7
.
e MUZO.& Magarita, R.; Piancatelli.
99% Tetrahedron Lett., 1995, 36, 3553
66%
Cativiela, C.; Figueras,F.; Fraile, J.M.; Garcia, J.I.; Mayoral, J.A. Tetrahedron Mt., 1995, 36, 4125 MeI, 18-crown-6, KOH CC4, ref’iux ,21h 66%
Abele, E.; Rubina, K.; Shymanska,M.; Kukevics. E, Synth. Commun., 1995, 25, 1371
adav. WC,; Kapoor, K.K. Tetrahedron, 1995,51, 8573 poly-L-leucine catalyst Ph
H202-NaOH-CH$12
Ph
85% (93% ee) Stichez, M.E.L.; Roberts, S.M. J. Chem. Sot., Perkin Trans. I., 1995, 1467
350
Section 367
Compendiumof Organic Synthetic Methods, Vo19
a
1. PhI(OH)OTs OPh
2. PhOH , K2C02, dry acetone
Ph
67%
Prakash. 0,; Saini, N.; Sharma,PK. J. Indian Chem. Sot., 1995, 72, 129
SECTION 366:
ETHER, EPOXIDE,
THIOETHER
[HC(Py)3W(N0)2(CO)I
PhCHO
- NITRILE
[sbF6)2
TMS-CN , rt , lh , MeNO
*
85%
Ph
Edller. J.W.; Gundersen,L-L. Tetrahedron Lett., 1993, 34, 2275 Ph
Me$iCHzCN , KF ,90 sec.
CN
PhCHO
w
Latouche, R.; w-Boullet.
lmicrowave TMSO . . F.. Hamelm. J, Bull. Sot. Chim. Fr., 1993, 130, 535
PhCHO
OTMS
TMSCN , MeCN , 20°C, 12h w
a chemoselectivereaction sinceketonesreactvery slowly
70%
Ph
CN 95%
Manju, IS.; Trehan. S,J. Chem. Sot., Per-kin Trans. I., 1995, 2383
SECTION 367:
ETHER,
EPOXIDE,
THIOETHER
- ALKENE
Enol ethersare found in this sectionas well as alkenyl ethers. 1. Jonesoxidation
m.
Bu &>
. .
82%
G,; Zhang, Y.; Dreyer, G. Tetrahedron Lett., 1993, 34, 449 1 PhMezSiH , hexane, rt OSiMQPh
0 o=
(PPh3)rnH
*
Chan. T.H,; Zheng, G.2, Tetrahedron Lett., 1993, 34, 3095
(t
/ 84%
351
Ether - Alkene
Section 367
/a Pd(PEW4
0 9 W03
9 DMF
60°C , 1.5h \
66%
OMe
4\/
OMe
Arcadi, A.; Cacchi. S;&qock. R.C.; Marinelli, F. Tetrahedron Lett., 1993, 34, 2813 OMe w
9rt OMe I
PhCHO 0.5% Yb(fod)3
addition of K2CO3preventsformation of this Deaton, M.V.; Ciufolini. M.A, Tetrahedron Lett., 1993, 34, 2409 TM
TM 1. iBuMgBr , cat. Cp2TiC12
~TBS
70% Tani, IS.; Sato, Y.; Okamoto, S.; Sate. F, Tetrahedron Lett., 1993, 34, 4977
r(i
Me H
+
1. OSM LiC104, ether 2.1N HCl , THF 15 min, 0°C t
\
NHBoC
6
OTBDMS (8: 1 threo:erythro)
. PA,; Moher, E.D. Tetrahedron Lett., 1993, 34, 5567
-YOEt OEt
1. Me2S , TMSOTf , -78OC * 2. PhSLi
-yoEt
J&I. S,; Park, J.H.; Lee, J.M. Tetrahedron Lett., 1993, 34, 5769
91% SPh
Compendiumof Organic Synthetic Methods, Vo19
352
x
Section 367
OMe OMe
b
,0.3 p-TsOH
neat, rt
Bn
71%
prlohr. P, Tetrahedron Lett., 1993, 34, 6251
g
y;~p;~s
Semmelhack.ML&; Epa, W.R. Tetrahedron Lett., 1993, 34, 7205
F3
Ph aPh
SEt
+ Ph CF3
Nti,rt,2h
I.3
(94:6 Z:E)
Beg&, J.-P.; Bonnet-Delpon, D.; M’Bida, A. Tetrahedron Z&t., 1993, 34, 7753
cf
OMe OMe
OMe TMSOf , iPr2NEt -2OOC + rt ,4h
Gassman.P.G.; Bums, S.J.; Pfister, K.B. J. Org. Chem., 1993, 58, 1449 SMe
II
1. catecholborane , 3% PdClz/dppf
2* phnBr
, reflux
aq. NaOH ,2h Gridnev, I.D.; Mivaura. N.: Suzuki. A,J. Org. Chem., 1993, 58, 5351
62%
Section 367
Ether - Alkene
‘*Me3siJcc1 , BF3.()Etzw c6H 13CHO
2. DBU/LiClO&leCN , 60°C
Wl
D’AnieUo, F.; Mattii, D.; Taddei. M, Synlett, 1993, 119
Ph#‘CH$H$IH
, &CO3
PhCl , heat Billeret, D.; Blondeau, D.; Sliwa.
MeCN
~y~the~~~,1993, 881
e,
52%
==c
2. NaOMe , heat
ue.
,OMe
1. MeOH, HCl,, , ether O°C,5d
OMe
Joglekar, B.R, Synth. ~u~~~~., 1993, 23, 1979
, PhH ) 100°C
Bu
3c Bu
sealedtube 6Me
62% ’
Harvey. D.F,; Neil, D.A. Tet~uhedr~n~ 1993,49, 2145
Ji, J.; b. X, .I. Chem. SW. Chem. Comun.,
0
1993, 764
NaOCl , Mn(salen) cat. 45% (64% ee)
\ I ether f 4-Ph-p~dine-N~xide Chang, S.; Heid, R.M.; bobsen. E.W, Tetruhedr~~ Lett., 1994, 35,669 Ph-C&H , PhH , 90°C ph/\s-+ AIBN , sealedtube Ph 2h 23% 65 Benati, L.; Capella, L.; Montevecchi, PC; Spagno~o,P. .I. Org. Chew., 1994, 59, 2818 Ph\/SH
354
Compendiumof Organic Synthetic Methods, Vol9
Section 367
Lee, G.H.; Choi, E.B.; Lee. E.: Bak. C,S, Tetrahedron L&t., 1994, 35, 2195 PhSH , Pd(OAc);! THF,50°C,14h
*
72%
Backvall. J.-E,; Ericsson, A. J. Org. Chem., 1994, 59, 5850 Br
-+
Ph
C02Me
CR-
Ph Ni(C0)4, MeCN , MeOH
76% (80:20 cis:trans)
Ni(C0)4, TlOAc , MeOH 66% (30:70 cis:trans) Llebaria, A.; Camps,F.; Moreto, J.M. Tetrahedron Lett., 1994, 35, 4011
De-A,:
HO
= Iz TMSOTf , CHg12, -76OC HO :ee = OH i)H 94% 94% (>99:1 a$) Toshima. IK; Ishizuka, T.; Matsuo, G.; Nakata,M. Tetrahedron Lett., 1994, 35, 5673 SPh +
CuOTf , PhH/THF ,25OC, 0.3 h
SPh
SPh an alternative to cuBreMe$ &hen. TJ Shook, C.; Thiruvazhi, M. Tetrahedron Lett., 1994, 3.5, 6041
mez.
SPh 99% SPh
ijc, :.:g::** 0 G,; Figadere,B.; Cl&y, P. Tetrahedron Lett., 1994, 35, 6295
Section 367
355
Ether - Alkene
1.2 q. ZuEt2 , cat. Ni(acac);?, THF 2.CuCNe2LiCl
Vaupel, A.; Knochel,.
T~trah~d$~n Lett., 1994, 35, 8349
PhSLi , LiC1 , Pd(PPh3)4
*
OTf
SPh
Tl-IF , reflux 89% A.G; Barciua, LO.; Cerezo,A. de F.; Su~r~~ian, I&R. ~y~~e~~, 1994, 561 1. HZrCp2Cl , THF 25OC, lh c6b-+==
2.
cx 0
Pereira, S.; Zheng, B.; &&m&J&J.
Cl’
*
Z-02
0, 0 wl3
76%
Org. Chem.,1995, 60, 6260
CpzTiMe2, THF ,65OC OMe
OMe 67% Petasis.N.A,; Lu, S.-P. Tetrahedron Lett., 1995, 36, 2393 M!vlPP , MeOH, rt
MMPP = mouoperoxyphthalatehexahydrate TYAnnibale, A.; Scettri. A, Tetrahedron L&t., 1995, 36,4659
YmrsoJc
91%
ems *
Ph
SnClz-AcCl , CH$$ ,4h 66% yama. T,; Ishiwata, A.; Sam, T.; Matsuda,T.; Takahashi,M.; Koga, G. Tetrahedron Let& 1995, 36, 5581
Section 368
Com~n~um of Organic Synthetic Methods, Vol9
356
S
W(OAr)(OPr)(CHCMe3)Cl(OEt)2 5c
ms-
quant.
0
Leconte, M.; Pagano,S.; Mutch, A.; Lefebvre, F.; met. 132, 1069
J.M Bull. Sot. Chim. Fr., 1995,
Section 18OA(Protectionof Ketones)
RelatedMethods:
HALJDE, SULFONATE - HALIDE, SULFONATE
SECTION 368:
H~~ycloprop~a~ons are found in Section74F (Alkyds from Alkenes). Cl&XC13 , toluene ,3h mph Sakai,;
Cl,&Ph 41% RuC12(PPh)3)3 , 120°C2, Sugimoto, K.; Shigeizumi, S.; Kondo, K. Tetrahedron L&t., 1994, 35, 737 1. Cl2 , NF3*OEt2
Cl
N-OH
-0
82%
2. HCI
Cl
Tordeux, M,; Boumi~e, K.; Whelp.
0
NOH
C,J. Org. Chem., 1993, 58, 1939 F
NO’BFi , PPHF
80% F
* (>< PPHF = pyridinium polyhydrogen fluoride York, C.; Prakash,G.K.S.; Wang, Q.; Olah. G.A,Synlett, 1994, 425
0I
Br
C l&XMe3Mn04 , Me3SiBr * CH2C12,O*C
Hazra. B.(lli; Chordia, M.D.; Bahule, B.B.; Pore, VS.; Basu, S. J. them. Sot., ~erkin Trays. l., 1994, 1667 /,
KIC12, Hfi )
Ph -I
/--Cl
/+--I +
Ph \
I 1) 94% _Zefirov.NS,; Sereda,G.A.; Sosonuk, S.E.; Zyk, N.V.; Likhomanova, T.I. Synthesis, 1995, 1359 Cl
(6
.
Section 369
Halide - Ketone
SECTION 369:
357
HALIDE, SULFONATE - KETONE 0
Cl hexane, rt
d
N I
92%
Cl
de Faria, A.R.; Matos, C.R.; Correia. C.R.D, Tetrahedron Let?., 1993, 34, 27 NBS , aq. MeCN , cat. HCI C02Et
rt ,6h
-
Br-C02Et 81%
-ton.
H.E.; Leanna, M.R. Tetrahedron Let?., 1993, 34,448l
1. ClCH21, MeLi , -78OC 2. MesSiCl , -78OC-+ rt
TMS
Et Cl
OEt * + Br Br Barluenm. J,; Pedregal,B.; Concellon, J.M. Tetrahedron Let?., 1993, 34,4563 OH Br 0
83%
HTIB ,12, MeCN , r-t; reflux ,20h F
HTIB = hydroxy p-tosyloxyiodo benzene
Bovonsombat, P.; &lcN&s. L Tetrahedron, 1993, 49, 1525 1. pyridinium polyhydrogen fluoride ‘O-c=)-’
2. :;;c,,, 3. &CO3
*
‘={rx--
61% Karam, 0.; Jacauesv.J.-C,; Jouannetaud,M.-P. Tetrahedron Let?., 1994, 35, 2541 Ph
1. PhCHO ,5% (BiC13*1.5ZnCl2) Ph y-y” zc 2. Me$iCl 0 Cl Le Roux, C.; Gaspard-Iloughmane,H.; Dubac. J, J. Org. Chem., 1994, 59, 2238
>88%
358
0 II ph/SvF
1.2 LDA ) THXWMPA ) -78°C 2. CgH1qcHU c
0 F
3. FVP (5~8OC) Reutrakul, V&; Kruahong, T.; Pohmakotr,M. Te~r~~e~~o~ Lett., 1994, 35,4853
82~48%
~~*~z,~Hz~~z rt , overnight 49% conversion Bovonsombat,P.; Angara, G.J.; McNelis. L Tetrahedron Mt., 1994, 35, 6787
NBS Yt-BuOH ) 30°C 1.5h
54%
,,
Coss~=J; Furet, N, ~~t~~~edru~ ~tt.~ 1995, 36, 3691 1. HZZrCp;1Cl 2. A&l, 15%CUB~~SM~~ w
3. NBS
Br C6h3
+
93%
zheng, B.; ~rebnik. M, Tet ra hed ran Lett., ~995~ 36, 5665
2.2 eq. FeCf3) DMF
fl;
”
-4m
Thompson, D.F. J, Chem,Sot., &&in Trans. -I., 1995, 23 15
f-j
Section 371
Halide - Nitrile
359
0 DMSO , (CoC1)2 t MeOH 93%
0 NEt3 , CH2C12, -6OT Raina, S.; w.
*
~
Cl
V.EL. Tetrahedron, 3995, 51, 2467 Ff12-HCO,H ,
30-lS*C ,2h * F
70% Chambers, R.D.; Greenhall, M.P.; Hutchinson, J. J. Chem. Sot. Chem. Conmun., 1995, 21
SECTION 370:
SLIDE,
SULFONATE - NITR~E
NO ADDITIONAL
SECTION 371:
EXAMPLES
HALIDE, SULFONATE - ALKENE 1. LDA 2. CIP(O)(OEt)2 0
I 3. TMS-I
Lee, K.; Wiemer. D.F, Tetrahedron Let?., 1993, 34, 2433
LDA , ether
Br Shino~u~, H.; ~
~t~oto.
K, Tetrahedron Let?,, 1993, 3#,4985
1. C13CCN 2.12 ) &CO3, ether b-
+ H
76% x 88% 7h5 C7H15
(33 Friesen. R-W,; Giroux, A.; Cook, K.L. Tetrahedron Let?., 1993, 34, i983
83%
360
Compendiumof Organic Synthetic Methods, Vol9
Section 372
85% O- F.-T,; Kumar, KA.; Hsieh, L.-C.; Wmg, R.-T. Tetrahedron Lett., 1994, 35, 2553
cat. Pd(OAc)z ‘ILiCl a+ G benz~uinone , 20°C $ t AcOH-acetone IBackvall. J.-E&;Nilsson, Y.I.M.; Andersson,P.G.; Gatti, R.G.P.; Wu, J. Tetrahedron Lett., 1994, 35, 5713 0
0
Iz,CAN,MeCN,5h reflux
I 55% (67/33 dlkwso)
6
C6h3
SiMe3
IPy2 BF4/2HBF4 , CH2C12
I
C6hJ
w
-
w
77% ~~~~~n~~ J,; ~v~ezaG~c~a, L.J.; Gonz~ex, J.M. Tetrahedron Lett., 1995, 36,2153
1. ICI, CH2C12, -78OC 2. NaOMe , -78OC
*
I/n/wll
43%
reversing order of ad~tion leadsto 38% of Z-iodoalkene Stewart, SK.; ~ SECTION
C3H-7
372:
CHO
Tetrahedron Lett., 1995, 36, 3929
KETONE
- KETONE
AC@, CoCJ2
MeCN Bhatia, B.; Punniyamurthy, T.; -1.
* C3H~~c~7
+
0 15% J, J. Org. Chem., 1993, 58, 55 18
C3H7~cH3
61%
0
361
Ketone- Ketone
Section 372
2 PhLi, THF , 20°C
30 min
eswff.
2
Ph
Ph
95%
*
-R0 UT,; Zhou, M. Tetrahedron Lett., 1993, 34, 571
Ph
P+MgBr THF , -7OOC
60%
RJtL; Iyer, V.S. Tetrahedron Lett., 1993, 34, 3683
OTMS
Bn
kc
9 Fq(W9 CO, ether I 2h
0 Zhou, T.; Green. J.R, Tetrahedron Lett., 1993, 34,4497
Ph
ph~oH
, DMF , O°C Mn(pic)s /
Ph Iwasawa, N.; Hayakawa,S.; Funahashi,M.; Isobe, K.; Narasaka. K, Bull. Chem. SOC.Jpn. 1993, 66, 819
Mohr, B.; Enkelmann, V.; Wegner. G, J. Org. Chem., 1994, 59, 635
Section 373
Com~n~um of Organic Synthetic Means, Vol9
362
OTMS
J
a
OTMS
*
0
BFs*OEtz
61%
J, Org. Chem, 1994, 59, 1485
Jenkins, T.J.; Burnell.,
0
0
Yb-TMS-Br 68%
THF , reflux I
K
Tanigychi. Y,; Nakahashi,M.; Kuno, T.; Tsuno, M.; Makioka, Y.; Takaki. K.: Fuiiwara. Y, Tetrahedron Lett., 1994, 35,411l OAc
Maikap, G.C.; Reddy, M.M.; Mu~opadhyay, M.; Bhatia, B.; &b&& 9145
Tetrahedron, 1994, 50,
H PCWP, DCE , reflux ,3h Bu
Bu + OH
mp
= bC5fkN(CH2)15Md3
Iwahama, T.; Sakaguchi,S.; Nishiy~a, Y.; m.
93% (~4~(0)(02)2bl 0 Y, T~tr~hedr~~ Lett., 1995, 36, 1523
REVIEW:
“a-Diones from Cyclic Oxamidesand ~g~o~i~iurn Reagents:A New, Generaland Environmentahy Beneficial Synthetic Method,” ~r=West~. UT,; Zhou, M. ~y~Ze~, 1994,975
SECTION 373:
KETONE
- NITRILE
, DCE ,70aC t 20% Pd(OAc)2nPPh3-dppb 65h LL Org. ~he~.~ 1994, 5%2679 Nozaki, IS.; Sato, N.; ma.
Ph
Phe
0
74%
Section 374
SECTION
Ketone- Alkene
374:
KETONE
363
- ALKENE
For the oxidation of allylic alcohols to alkeneketones,seeSection 168 (Ketones from Alcohols and Phenols) For the oxidation of allylic methylenegroups (C=C-CH2 + C=C-C=O), see Section 170 (Ketonesfrom Alkyls andMe~ylenes). For the ~yla~on of alkeneketones,also seeSection 177 (Ketonesfrom Ketones)and for conjugatea~ylations seeSection74E (Alkyls form Alkenes).
4 Meo2cer-o
PdC12(PhCN)2) 50°C SnC12,MeCN y33h Masuvam~ Y,; Sakai,T.; Kurusu, Y. Te~r~~e~~~~ L.&t., 1993, 34,653 OCO2Me
Das, N.B.; Sarma,J.C.; Sharma. R.P,; Bordoloi, M. Tetrahedron Lett., 1993, 34, 869
w
SnBu3
)
AIBN
m.
G.A.; Andersh, B.; Su, Q.; Shi, J. Tetrahedron Lett., 1993, 34, 1741 P 1.
wm5 ?== Me0 50°C ,3h, SiO2
2. CAN, O.lM aq. HNO3 rt, 20 tin Harrity, J.P.A.; Kerr, W.J,; Middlemiss, I>. Tetrahedron Lett., 1993, 34, 2995
86%
364
Com~n~um
&
C02Et
of Organic Synthetic Methods, Vol9
Section 374
1. PhH , Cu(OAc)2@2H@ Pb(OAc), ,2d
CO2Et
2. ethylene glycol , CH2C12
\
* & Schultz, A.G.; Holoboski, M.A. Tetrahedron Lett., 1993, 34, 3021
MI-O, CHfl12, rt t
-+*,,,w
SiOdA1203
MT0 = methyltrioxorhenium Junga, H.; Blechert. S. Tetrahedron Lett., 1993, 34, 3731
Mo(C0)6 , DMSO , Toluene 100°C ,12h Jeonrr. NJ Lee, S.J.; Lee, B.Y.; ~hung, Y.K. Tetrahedron Lett., 1993, 34,4027
Br
Yu, Y.; Lin, R.; m.
SmIy,THF,rt,2h 02N*cHo
*
p~No2
Y, Tetrahedron Lett., 3993, 34, 4547
CHCl3 , rt ,8h
TBDMSA
TBDMS
Konopelski. J.P,; Kasar, R.A. Tetrahedron Lett., 1993, 34, 4587
78OC
Section 374
Ketone - Alkene
365
BufinH , AIBN, 60°C syringe pump (3h) ,O.O2M
Rawal. VH,; Zhong, H.M. Tetrahedron Lett., 1993, 34, 5197
Bu3s-YoEt I Bu 3SwOEt
hJL hJL
n
OEt
OEt P 0.01 PdCl2(MeCN)2, 20°C 75% * * DMF ,2h OEt Par-rain, J.-L.; Beaudet, I.; Duchene, A.; Watrelot, S.; Quintard, J.-P. Tetrahedron Lett., 1993, 34, 5445 P
Cl
FLke2
CF$E 88%
CH2C12, reflux ,96h Ales, C.; Janousek, 2.; Viehe. H.G. Tetrahedron Lett., 1993, 34, 5711
CF?
1. BuMgBr , 10% CuI, TMSCl HMPA , THF , -78OC 2. CH212 ,2 eq. Et2Zn
biker-Milbum.
))
c
3.2.2 eq. FeC13 , DMF , O°C - B+3=099x93x54% 4. NaOAc , MeOH M.1,;Thompson, D.F. Tetrahedron Lett., 1993, 34, 7291
slzN&$ fast addition
(2:l z:E) 70% Sha. C.-K,; Shen, C.-Y.; Jean, T.-S.; Chiu, R.-T.; Tseng, W.-H. Tetrahedron L&t., 1993, 34, 7641
366
m;
Com~n~um of ~g~ic
Syn~e~c Means, Vol9
Section 374
Kassir, J.M.; Semones,M.A.; Weing~en~ M.D. T~~~~~~~r~~L&t., 1993, 347853
; Riesinger, S.W, J, Org. Cafe,, 1993, 58, 408
Me
11
.*
\
27)
~7%
Ihle, NC.; Heathcock. CH, J, Org. Gwen., 1993, 58, 560
( Ew~2zn EtQgz
II
Bu CuBrGMe2, HMPA TMSCl
C02Et 65%
C~mmins. M.T,; ~~te~et, P,XX; Trotter, B.W.; Vatlin, I.M.; Watson,P.S.; McKerlie, L.A. Reinhold, T.L.; Cheung, A.W.; Stetson,K.A.; Dedcpoulou, D.; Gray, J,L. J, Org. Chem., 1993, 58, 1038
Section 374
Ketone - Alkene
367
0
0
53%
2.2 eq, CuSO4, llO°C Trost. B.M; Parquette, J.R. J. Org. Clef.,
1993, 58, 1579
co2(c0)8, MeCN rt -9 75OC
91% *
Me
0
Hove. T.R,; Suriano, J.A. J. Org. Chem., 1993, 58, 1659
2 eq. PhCHO , ZrOC&8 IT20
Ph 73%
Yuki, T.; Hashimoto, M.; Nishiyama, Y.; Ishii. Y,J. Org. Chem., 1993, 58, 4497
Ph
z=z=
Ph Ph
5% Pd(OAc)z ,4 NaOAc 100°C, DMF , BQNCI 84%
Ph
Larock, R,C; Doty, M.J.; Cacchi, S. J. Org. Chem., 1993, 58, 4579 0
Bu
W(CO)6, THF , CO, sealed tube BU
hv ,65OC j,
llO°C
J. Am. Chem. SW., 1993, 115, 1154
0
Co~~n~u~
368
TMS
of Organic Syn~e~c Mean,
PhC=CH , S&14-NBu3
w
~ l .
-A.;
I
Section 374
Vo19
Ph
~ 85% (203 Ez)
’ Hirarna, M. J. Am. Chem. Sot., 1993, 115, 3362
0 In--f
0 Ph
5% RhCl(PPh3)3,toluene , 120°C
Ph *
3 huffs,
~ 84%
M.A.; ~,ie~eskind. L.S, J. Am, ~~~~* Sm., 1993, 115, 4895 Me$KN Cp2Ti(PMe&
Berk, S.C.; Grossman,R.B.; Buchwald. S.L,J. Am. Chenz. Sm., 1993, 115, 4912 COzMe
CO, 10% Pd(OAc)z-dppp Phi-MeC~-MeOH
r
&&U&N. T,; Tsuji, J.; Tsujiguchi, Y.; S;zito. S, J. Am. Chem, Sm., 1993,
TiC14, CHg12, -40°C, lh
81% 0 115,
5865
C02Et
OMe funk. I?J& Fingered, J.F.; Olmst~ad,T.A,; Para, KS,; Wos, LA. J. Am. Clef. Sot,, 1993, 115,8849
Ketone- AIkene
Section 374
I B”
II
~
369
, 10% (c~)CpRuCI OH
20% NH4PF6, neat, 1OOOC
Bu
B-M,; Martinez, J.A.; Kulawiec, R.J.; Indolese, A.F. J. Am. Clef. Sot., 1993, 115, 0
PhCHO ) SnCIz , Na2SO3
Br Ph~ Lin, R.; Yu, Y.; Zhang Y, Wyatt, C~~~~.,
-
PhTPh
73%
0
1993, 23, 271
tduene , sealedtube ,23”C -+ 50°C
Srikrishna. A,; Krishnan, K.; Van Kateswarlu, S. J. Chem.Sm. Chem. Coals.,
&
1, D;ue
1993, 143
, SnQ- Bu3N
70%
~~
Ph auchi. MJ Sehata,M.; Hayashi, A.; Hirama, M. J. Chem.Sot. Chem. Comnzun.,1993,
Bu’-\-(
PPh3, EtOH , PhH 0
reflux
72%
0
Guo, C.; Lu. X, J. ~~~. Sm., Pe~~~~Trans. I., 1993, 1921 +gb+%-
SePh
SnBug
AIBN , toluene
Watanabe,Y.; Yoneda, T,; Okumura, T.; Ueno, Y.; Tom T, Butt. Chem.Sm. Jpn., 1993, 66, 3030
370
Compendiumof Organic Synthetic Methods, Vo19
Section 374
H
0
0.01 mol dmB3 toluene , reflux
b&&&u&;
a I-f
-~
0 53% Takada,K.; Odagaki, Y,; hoe. S, .I. Chem. Sot. Chem. Commun., 1993, 556
l
0 2. 3. 1. BuGnOSnBu3 PhCHO H20 , (-C02) , HMPA 0 Nishio, M.; Baba, A.; Mats&a, H. Chem. Lett., 1993, 1219
%0 mT.:
62%
t
1. Me&I , CHQ , rt ,30 min 2. PdC&(MeCN)2,9h
4
SiPh3
siPh3
w
/
64%
Degl’Innocenti, A.; Capperucci,A.; Bartoletti, L.; Mordini, A.; Reginato,G. Tetrahedron Lett., 1994, 35, 2081
CM% 6
~seo2H~p~~~
~OH
+ ~
leq.,rt,14h 35% 2 eq., 20°C, 14h 20% 2 eq. , reflux ,2h Barton. D.H.R; Wang, T.-L. Tetrahedron Lett., 1994, 35, 5149
36% 75%
90%
Li
0
Ph~
e(
me2
OEt
*
Ph j;r
enolate free a-alkoxy vinyllithium reagent improved prep & procedure Shimano, M.; Meye;rs.AJ, Tetrahedron Lett., I994, 35, 7727
OEt 90%
Section 374
Ketone- Alkene
371
I
C5Hll
TMSCl , MeCN , rt ,3h Me -c
I o. F.-T,; Hsieh, L.-C. Tetrahedron Lett., 1994, 35, 9585
3% co2(co)fj
co,
EtOg
w
3, DME , Id
92%
0
Eto
EtO?C 82%
Jeong. N,; Hwang, S.H.; Lee, Y.; Chung, Y.K. J. Am. Chem. Sot., 1994, 116, 3159 Ph CpzTi(PMe& , Schlenk tube Me$iCN , PhH 80%
Berk. S.C,; Grossman,R.B.; Buchwald. SL, J. Am. Chem. Sot., 1994, 116, 8593 NHMe Meu
1. PhMgCl , CeC13, -78OC, THF * 2.10% AcOH
Me
MYYMe Ph
0 85%
Bartoli. Cr,;Cimarelli, C.; Marcantoni, E.; Palmieri, G.; Petrini. M, J. Chem. Sot. Chem. Commun., 1994,715 I!!7
0
0
3. 1.MeCH(Cl)SPh KH CO2Me
2.ZnCl2
4. DABCO
c!b Amecke, R.; Groth. I J,; Kohler, T. Liebigs Ann. Chem., 1994, 891 MST J= C3H7
*
90x88%
TiCI4 , LiAlH4, CC4 CHEt
C3H +
f4=i
Mitani. M,; Kabayashi, Y. Bull. Chem. Sot. Jpn., 1994, 67, 284
63% (2)
Cl
Et
Section 374
Compendiumof Organic Synthetic Methods, Vol9
372
16 /l/I
,rt,3min Sn@HMPA
2.MeOH,rt,3min 3.0.1 N aq. HCl , rt 3 min
.
(9
1) 84%
Miyoshi, N.; Takeuchi. S,; Ohgo, Y. Bull. Chem. Sot. Jpn., 1994, 67, 445 PhCHO , Ni(cod)zPPh3, Zn
*
ph-Y 52% OAc 0 Masuyama. Y ,; Sakai, T.; Kato, T.; Kurusu, Y. Bull. Chem. Sot. Jpn., 1994, 67, 2265 dioxane ,6O*C, 4d
0
2 eq. Mn(OAc)s , Cu(OA& * AcOH ,8O*C
c
CD 0
52%
er. B&; Cole, B.M. J. Org. Chem., 1995, 60, 5376
C -I.;
t-BuMe$iH , Rh4CO) 12 CO, PhH , reflux 14%
63% Ishibashi, H.; Ii, N. Tetrahedron Lett., 1995, 36, 241 0
0 A
x
co(co)4
NaH **
X=NHTs X can also be OH, CHNO2, C(CO2Me)z Bates. R.W,; Devi, T.R. Tetrahedron Lett., 1995, 36, 509
X=NTs,69%
Section 374
Ketone- AIkene
373
2.25 CAN, DMF , O°C, 1.75h
F-vans.P.&, Longmire, KM.; Modi, D.P. Tetrahedron Lett., 1995, 36, 3985 0 e’ , clots 81% -
SiMe3 Chueh, L.L.; Tsay, S.-C.; fIwe
Lin.; .,,c7c15
C02Et
4
SiMe3
Tetrahedron Lett., 1995, 36,4093
PPh3m-hul~
,“,“,”
I toluene
ylyco2Et #
82% SaW, M.K.E.; j?elIicciari. R, Tetrahedron Lett., 1995, 36, 4497
Resek,J.E.; Mevers. A& Tetrahedron Lett., 1995, 36, 7051 OMOM EtO$-
ZnI
Me$iCl , CuCN , HMPA EtO$~;
l
.
68%
Huang, S.; Guise, L.E.; Lacy, D.B. Tetrahedron Lat., 1995, 36, 7061 0
Ph-Bt Bt = benzotriazole
1. BuLi * 2. cyclohexanone, ZnBr2, toluene llO°C, 12h c
60% Katritzkv. A.R,; Xie, L.; Toader, D.; Serdyuk, L, .I. Am. Chem. Sot., 1995, 117, 12015
Ph
374
Compendiumof Organic Synthetic Methods, Vo19
iPrNO2, DBU , MeCN
Section 375
4
65%
rt ,4h
Balllnl.,
Bosica, G. Tetrahedron, 1995, 51,4213
78%
Bates, R.W,; Rama-Devi, T.; Ko, H.-H. Tetrahedron, 1995, 51, 12939
8% MeReO3, C13CCF3
reflux ,5d 80%
Schneider,M.F.; Junga, H.; Blechert. S, Tetrahedron, 1995, 51, 13003 Ph Ph
=
Ph
, toluene ,135OC
WH)2(CW’P~3)3 7lh
85% (9:l)
Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai. S, Chem. Lett., 1995, 681
SECTION 375:
NITRILE - NITRILE NO ADDITIONAL EXAMPLES
375
Nitrile - Alkene
Section 376
NITRILE
SECTION 376:
- ALKENE
l.LDA,THF, 3 eq. HMPA , -78OC
phTCN
2. Me1 , -78OC
NMePh
*
,mcN
81%
NMePh
Me 100% z
Chang, C-J.; Farm, J.-M,; Liao, L.-F. J. Org. Chem., 1993, 58, 1754 I. PPh3, PhH ,rt PhhN3 I Ph
2. Ph$=C=O , PhH , rt
51% Molina. P,; Alajarb, M.; Lbpez-Leonardo, C.; AlcGntara, J. Tetrahedron, 1993, 49, 5153 1. Me$iCH2MgCl,
THF , -2OOC 36%
2. PC13, THF ,67OC so. H.-E, Gilbert, B.A.; Hwu, JR. J, Check Sot. Clef.
C~~~n.~
1993,669
2 LiCN ,0.07 Pd(PPh3)4 0.07 12-crown-4
UTf
CN
PhH,rt Piers. E,; Fleming, F.F. Can. J. Chem., 1993, 71, 1867 CN Cl
/==-c
CN
0
CN
c.3
MezN=CClz Cl, CH$& 2 eq. NEt3 , -15*c
Cl *
Me2N
+
79% Bouvy, D.; Janousek, 2.; Viehe, H.G. ~~~2,Sot. Chum. Belg., 1993, 102, 129
Yamamoto. Y;, Al-Masum, M.; Asao, N. J. Am. Chem. SM., 1994, 116, 6019
CN
Section 377
Cum~n~um of Organic Synthetic Methods, VoI 9
376
1. Pd&dba)3eCHC13 , 10h
Me
a 2. /y/Pr
,4%CuI,2eq.~,D~
PdCI(PPh3)~CH~h), rrt ,4h Suginome,M.; Kinugasa, H.; Ito. Y, ~e~r~~e~r~~Lett., 1994, 3.5, 8635
Et02C\/CN
-CHO
, TfQT
* *co2Et 6% RuH2(PPh3)4 83% b ur&&hi. . S. I.: Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya. S,; Mizuho, Ye; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Sot., 1995, 117, 12436 Ph-
KCN , DIvIF , NiBr2(PPh3)2 * Zn , PPh3, 50°C
Br
PhwcN
99% (95f5 En) Sakakibara,Y.; Enami, H.; Ogawa, H.; Fujimoto, S.; Kato, H.; Kunitake, K.; &saki. K,; Sal& M. Bull. Chem. Sot. Jpn., 1995, 68, 3 137
SECTION 377:
ALKENE
- ALKENE
1. (Me2N)+CHZ 4 eq. NaN(SiMe3)2
*
C13TiO 2. 5
eq.
c3
CHO
Reynolds, K.A.; Dopico, P.G.; Sunde~ann, ML; Hughes, K.A.; Finn. M,G,J. Org. Chem., 1993, 58, 1298 1. Cp2ClZra GoH21--CHO
SnBug
CH2C12 2. BF3*OEt2 Maeta, H.; Hasegawa,T.; &uki. M, Synlett, 1993, 341
D-
c a21
N
92% (96:4 EZ)
Alkene - Alkene
Section 377
377
Bu
OTIPS
Bu (cod)RuCpCl
mt.
..
11 R .W; Indolese, A. J. Am. Chem. Sot., 1993, I 1.5, 4361
4) 68%
Ph ,OPh (fp\
0 -20°C , lh
C7Hl 4 Yanagisawa, A.; Hibino, H.; Nomura, N.; Yamamoto. H, J. Am. Chem. Sot., 1993, IIS, 5879
ZnCl PdW’bh , m--n?,rt Mazal, C.; Ultier.
M, Tetrahedron Lett., 1994, 35, 3089
B” Bu
=
Bu 3. cat. CuCV2LiCl , hcl 50°C, lh
-
Bulc 87%
Takahashi. T,; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett., 1994, 35, 5685 Br 1. CjH llMgB , NiClz(dppe) , THF 2. PhMgBr , NiQ(dppe)
Ph
PhS/ W-h */ 52% Babudri, F.; Fiandanese,V.; Mazzone, L.; Naso, F, Tetrahedron Lett., 1994, 35, 8847
378
Compendiumof Organic Synthetic Methods, Vol9
Br
$”
Section 377
Ph
, Pd(OAc)2, 10 kbar ,2d
PPh3, NEt3, TI-WMeCN , 20°C * c Voigt, K.; Schick, U.; Meyer, F.E.; de Meijere, A. Synlett, 1994, 189
0
Schmitz, C.; Harvey, J.N.; Viehe. H.G. Bull. Sot. Chim. Belg., 1994, 103, 105
(65 35) 91% Araki, S.; Imai, A.; Shimizu, K.; Yamada,M.; Mori, A.; Buts&an. Y,J. Org. Chem., 1995, 60, 1841
n
I
Pd(OAc)2, TPPTS aq. MeCN , iPr2NH 5
CO2Me P BU-
BuT 80%
C02Me
3
&O
Genet,J.P.; Linquist, A.; Blart, E.; Mouries, V.; Savignac,M.; Vaultier, M. Tetrahedron Lett., 1995, 36, 1443 COzEt lbleF$%~C6H13
Pd(OAc)2, PPh3,DMF ,28h rt , sealedtube Ph Matsuhashi, H.; Hatanaka,Y.; Kuroboshi, M.; Hivama. T, Tetrahedron Lett., 1995, 36, 1539
Section 377
Alkene - Alkene
379
Ph Yoshida, A.; Matsumoto, S.; Feng, IF.;Matsumoto, Y.; Sugino, A.; Hanamoto,T.;
. Mlkaml,; &
Tetrahedron
1995, 36,907
ktt.,
/
OSiMe3 d-
SiMe3 w
10%ZnClz , CH$& 25OC, L5h Ph
+ f I Ph
(22
.
78) 94%
Furuhashi, K.; Natsume,H. Tetrahedron L&t., ;995, 36, 5243
BT.;
I
Bu
Bu OH
, IXvlF:Hz(,
C3H+V
5% Cp~u(~)Cl
, loo°C
C3H7
st. B.M; Indolese, A.F.; Miiller, T.J.J.; Trepton, B. J. Am. Chem. Sot., 1995, 117, 615
Bu
ZZZ
Bu
1. Cp2ZrEt2 2. CHz=CHOEt
Bu
Bu w
3. H+
m
.
50%
T; Kondakov, D.Y.; Xi, 2.; Suzuki, N. J. Am. Chem. Sue., 1995, I1 7, 5871
380
Compendiumof Organic Synthetic Methods, Vo19
Me$i
=
WoPh
Section 377
9 PMe3
w-h3 CPa-BU2
81% Suzuki, N.; Kondakov, D.Y.; Kageyama,M.; Kotora, M.; Ham, R.; Takahashi.T, Tetrahedron, 1995, 51, 4519 Ph 10% RhCl(PPh3)3,PhMe
*
110°C * 80% Wender. P.k; Takahashi, H.; Witulski, B. J. Am. Chem. Sot., 1995, 117, 4720 1. TaCl5 , Zn , DME , PhH 2. THF w-h-w11
3. -0
Li+
4. aq. NaOH 65% T.&G. K,; Yamada,M.; O&&a, H.; IJtimoto. K,; Fujii, T.; Furukawa. I, Chem. k-K 315
19%
1. :cc12 C6H1-TMs 2. CsF 9DMF * cald/ . . m. &; Kobayashi, Y.; Koyama, K. J. Chem. Sot., Perkin Trans. l., 1995, 653
(95
.
72%
5) 86%
Yanagisawa,A.; Hibino, 1-I.;Habaue,S.; Hisada,Y .; Yasue, K.; Yamamoto.H, Bull. Chem. Sot. Jpn., 1995, 68, 1263
381
Oxides - Alcohols
Section 380
OXIDES - ALKYNES
SECTION 378:
0 * piTo Leonine,
1.2eq. Bu$nC=CBu , DMF 2% Pd(MeCN&12 rt,30min
l
SECTION 379:
77%
J.A.; Ventura, M.P. Te~ra~edrun Let& 1993, 34, 3663
OXIDES - ACID DERIVATIVES NO ADDITIONAL EXAMPLES
SECTION 380:
OXIDES - ALCOHOLS, THIOLS
Domfnguez, E.; w.
J.C Tetrahedron Lett., 1993, 34, 5803
OEt / P-- OEt \
MePO(OEt)z, BuLi , THF BF3*OEt2,-78OC
0
Li, 2.; Racha, S.; Dan, L.; El-Subbagh, H.; Abushanab.
MeO-PhCHO
83%
J. Org. Chem.,1993, 58, 5779
R
P Me0
\
H
+ 10%Li binaphthalenide, TI-IF
Ph
Me&’ Me0v
98% (20% ee) OH
Rath, N.P.; Spillincr. C.D, Tetrahedron Lett., 1994, 35, 227 0
, SmI2,THF
S02Ph 71% Te~ra~edrun Lett., 1994, 35, 5441
382
Compendiumof Organic Synthetic Methods, Vol9
Section 380
OH = E P
3.3 eq. La-Li-(R)-BJNOL complex MeNO*, THF , -40°C, 72h
CHO NPhTh
-+
NPhTh
NO2
99%
(99:l erythro:threo; 96% ee) N Tetrahedron Lett., 1994, 35, 6123
Sasai,H.; Kim, W.-S.; Suzuki, T.; wi.
l.LHMDS,O”C 2. PhCHO , 0°C 3. HCl , EtOH
92) 62% (8 VJ$.; Worrall, J.M.; Adams,H.; Alexander, R. Tekahedron Lett., 1994, 35, 6167
-al.
0
1. EtLi
0
0 t
P Ph’ II1Jk Ph
3.10% AcOH 2. CeC13, THF , -78OC
OH
P Ph’ II14 Ph
Et
71% Bartoli. G,; Sambri, L.; Marcantoni, E.; Petrini, M. Tetrahedron Lett., 1994, 35, 8453 vyOH
H202
OH . . ovicelll.
; w.
.
9 TS-1
4oH * 0
TS-1 = metal dopedzeolite
quant. P,; Sanetti, A.; Mincione, E. Tetrahedron Lett., 1994, 35, 8477 Ph S02Ph 1.2BuLi,THF
# Ph
2. t-B&OH, 15h -7OOC+ 2o”c 90% (55:45 erythro:threo)
Chemla, F.; Julia. M; Uguen, D. Bull. Sot. Chim. Fr., 1994, 131, 639
Section 383
Oxides - Amines
383
Bakers yeastI 4h
tiNo2
74% (99% ee , S)
uama. A,; Occhiato, E.G.; Spinetti, L.M.; Vallecchi, M.E.; Scaarpi, D. Tetrahedron, 1995, 51, 1775
SECTION 381:
OXIDES - ALDEHYDES CO/H2 (600 psi) , CH2C12 98%
Totland,K.; A,lpgr. )t J. Org. Chem., 1993, 58, 3326
SECTION 382:
OXIDES - AMIDES M BnNH2, NaH ,2.5h
9R 99
) TolO$ NHBn Me%,,, TolO$ + 82% * Cl Satoh, T.; Motohashi, S.; Kimura, S.; Tokutake, N.; Yamakawa, K, Tetrahedron Lett., 1993, 34,4823 1. CAN, MeCN , NaN02, Id 2. Hz0
NO2
64% NHAc Reddy, M.V.R.; Mehrotra, B.; Vankar. Y,D, Tetrahedron Lett., 1995, 36,486l
SECTION 383:
OXIDES - AMINES
,CO,Me Nw
p-TolS02SePh AIBN , PhH reflux
Brumwell, J.E.; Simpkins. N.S.; Terrett, N.K. Tetrahedron L&t., 1993, 34, 1215
Section 384
Compendiumof Organic Synthetic Methods, Vol9
P\
C3HW
OEt
95°C) neat, 6Oh
Ruder. S.M; Norwood, B.K. ~e~r~~e~r~~ Lett.,
1994, 35, 3473
X
X NO2
\ I
bakers yeast, 4d
m
/
kv
NO2
NH2
\
+
I
/I
Q NO2
No,
3) 37% X = Et (1 1) 36% X = OMe (5 Davey, CL.; Powell, L.W.; Turner. NJ,; Wells, A. Tetr~h~d~o~ L-e& ~99~, 35, 7867 l
. l
N-Tr
NHTr = =
[La, BINOL , Li] , THF =c dp
H
H. PCOMe
II OMe 0
, 60°V, 18h
Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki. NJ.
Ph
Me0
47% (69% ee) Org. Chem, 1995, 60, 6656
OXIDES - ESTERS
SECTION 384:
MeO-ri!
II 0
* /
0 II
1.2 eq. BuLi , Ph$ZH , -78’C MeO-P
2. ClC02Me, -78OC
/ -c
Me0
80% Geirsson. JKF,; Njardarson,J.T. Tetrahedron L&t., 1994, 35, 9071
Ph
CO2Me
Section 385
Oxides - Ethers
385
I
C02Et
73~92%
Short, KM.; Ziegler Jr., C.B. Tetrahedron Let& 1995, 36, 355
SECTION 385: OXIDES - ETHERS, EPOXIDES, THIOETHERS
2
l.Nti,THF,rt
PJ
ph\/
NO2
I,
84% NO2
, -4oOC
3.1NHCl Duffy, J.L.; Kurth, J.A.; Kurth, M.J, Tetra~dron Lett., 1993, 34, 1259 QH tz
=
SO2Tol
OH = t=
LiOOt-Bu , THF rt ,2h
72~ Bueno, A.B.; Carrefio, M.C.; Ruano. J.L.G. Tetrahedron Lett., 1993, 34, 5007 Ph$=CHz, O~/MII(OAC)~ AcOH , 80°C SOzPh Qian, C.-Y.; Nishino, H.; m Ph/\/\/S02Ph
Chemla, F.; m
‘* Bdi’ THF ) 2.5 eq. Me3Si~t-Bu ph/\/ysqph -4OOC916h 92V0
oTMs
&; Uguen, D. Bull. Sot. Chim. Fr., 1993, 130, 547
Et P
J. Heterocyclic Chem., 1993, 30, 209
PhSeTos, Ru(bpy)y2” MeCN , hv
Et 75% -
/f+-o Tos
SePh on. D.H.R; Csiba, M.A.; Jaszberenyi,J.Cs. Tetrahedron Lett., 1994, 35, 2869
386
Compendiumof Organic Synthetic Methods, Vol9
SECTION 386:
Section 387
OXIDES - HALIDES, SULFONATES AgN03 ) SO&$, MeCN
Ph-s--CH
w
3
9I Ph- +‘I
85%
YAK; Shin, H.H.; Park, Y.J. ~y~~~e~~~,1993, 209 so2t-Bu
1. BuLi, THF, -78°C
2. (PhS~~2~ m, .
V,; Beaulieu, F.; Muhri, K.; Han, W.; Mushy, C.K.; Davis, F.A. ~e~r~~~~r~~tee, 1994, 35, 3465
SECTION 387:
OXIDES - KETONES 1, c(No2)4
9 C5&2
0.17h, rt 2.KF,H20 Rathore, R.; Lin, 2.; Kochi. J.K, Tetrahedron Lett., 1993, 34, 1859 THF,rt,30min
Ph02S
0
+
Mk
EtO.!,
/Nd)-I
EtCf H Koh, Y.J.; ah, D.Y, Tetrahedron Lett., 1993, 34, 2147
Et0
Me 7~%
Me3SiCH2MgC~, m w=
-30°C -+ O”C, Ih
85%
Ballini, R.; Bartoli. GJ ~iov~nini, R.; M~cant~ni, E,; IPetrini, M, T~trah~dr~~Let&, 1993, 34,330.l
N Ph~
; C-cdirll
1, BnSO&X , NEtg , rt w
2.3N HCI
Me Kataoka. T,; Iwama, T. ~y~Zett,1994, 101.7
S&Bn
79%
Section 389
Oxides - Alkenes
387
NO2/O3, CH2Cl2 99% (o:m 52:48)
uzuk.~ H,; Murashima, T. .I. Chem. Sot., Perkin Trans. I., 1994, 903
a’ h-A
P
,C02Et
1. LDA , THF , -9OOC
Me
J? lllllllllls
t P
02Ph
C02Et
55%
(2:l dr)
PpMe Datta, A.; Schmidt. R.R, Tetrahedron Lett., 1993, 34, 4161 (EtO)$QNa , THF, rt ,5h 60% Kim. D.Y,; Kong, M.S. J. Chem. Sot., Perkin Trans. I., 1994, 3359 Me3SiNO3,CrO3, MeCN , Id 61% Redy, M.V.R.; Kumareswaran,R.; Vankar. Ya
SECTION 388:
Tetrahedron L&t., 1995, 36, 7149
OXIDES - NITRILES NO ADDITIONAL EXAMPLJZS
SECTION 389:
OXIDES - ALKENES Ph
Ph 9 II-IF SnBug 2% Pd2(dba)3mCHC13 reflux
TolPale?. R&; de Dios, A.; de la Pradilla. R.F, Tetrahedron L&t., 1993, 34, 2429
87%
388
Compendiumof Organic Synthetic Methods, Vol9
S&Me
0302
Section 389
9 ld
*
Meo-y
55%
t-BuOH Philips, E.D.; Whitham, G.H. Tetrahedron Lett., 1993, 34, 2541 1. BuLi PhOe 96 x 92% 93:7 (E:z)
Funk. R.L,; Unstead-Daggett,J.; Brummond, KM. Tetrahedron Lett., 1993, 34, 2867 Ph
BF3*OEt2,rt * CH2C12
75%
Duffy, D.E.; Condit, F.H.; Teleha, C.A.; Wang, C.-IA; Calabrese,J.C. Tetrahedron Lett., 1993, 34, 3667 G
PhS02Na, THF O*C,30 min
17
t PhOfi h
m
. .
0’”
SO2Ph
0 BF4
M.; Oshima, K.; Masaki, Y.; Kunishima, M.; Tani, S. Tetrahedron Lett., 1993, 34,
4829
5% Pd(OAc)z ,5% dppp (PhSO$$H2, THF
7o”c
82% Trost. B.M; Zhi, L.; Imi, IS. Tetrahedron Lett., 1994, 35, 1361
7%
389
oxides - Alkenes
section 389
5% P~(PPh3)4, NEt3 5 eq. AgN3 , MeCN reflux ,3Sh wS02Ph
1. PhCHO , NaH , THF 2. t-BuOK , DMSO
p(ow2
// 0 Kiddle, JJ.; ~
0 95~85%
J. Org. C~em.~1993, 58, 3572 OEt ~*2B~i,2~PA~T~ -78OC + l-t 2. aq. NH&l
SO$‘h SOzPh +
02Ph 25) 53% (75 m, Bolton, G.L.; Brummond, KM.; Ellestad, K.E.; Stall~an, 3.B J, Am. Chem. Sot., 1993, 115, 7023 l
l
no yield Schonk, R.M.; Bakker, B.H.; ~fon~Recl.
Trav, Chim. Puys-Bas, 1993, 112, 201
S02Tol Harvey, 1.W.; While.
G.H, J. Chtmt. Sot., Perkin Tram I,, 1993, 185, 191
390
Compendiumof Organic Synthetic Methods, Vol9
OTIPS
Section 390
6:
OTIPS
Bu@NO3, TFAA , 0°C ,30 min 49% &am
P&-Longmire, J.M. Tetrahedron L&t., 1994, 35, 8345
NO2
H PPh3/CC~t3,
Me
reflux , 1.5h )
Ph ~
NO2
Ph T
Me
90%
NO2
Saikia, AK.; B
N.c; Sharma,R.P.; Ghosh, A.C. ~y~the~~~, 1994, 685 CAN,10NaN02,2AcOH,4h
NO2
sealedtube, 73OC, CHCl3 *
0
86% mu. J&, Chen, K-L.; Ananthan, S. J. Chem. Sm. Chem. Commun., 1994, 1425 Me+=-\
l.NCS,PhCl,rt 2. mcpba, CH&$ , -2OOC
,Ph ‘-Ph II 0
Ph )
Cl
w
3. LDA , -40°C, PhCHO
95x75% Otten, P.A.; Davies, H.M.; yan der Gen. 4 Tetrahedron L&t., 1995, 36, 781 b
,/S@Ph
S’ II 0
S02Ph
.
iHIIIIIS02Ph Delaunay, J.; Orliac, A.; Simonet,
70% Tetrahedron Mt., 1995, 36, 2083
DCE , NO (10 atm) , acidic Al203 reflux T.; Hata, E.; Yamada, T. Chew. Mt., 1995, 505
Mu~y~~
SECTION 390:
OXIDES - OXIDES S02Ph
1. BuLi , ether, -78OC 2.0.5 Tf20
/ Mahadevan, A.; Fuchs. P.L, Tetrahedron Lett., 1994, 35,6025
Me
Compendium of Organic Synthetic Methods, Volume 9. Michael B. Smith Copyright 2001 by John Wiley & Sons, Inc. ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)
Author Index
Aase, K. Abarbi, M. Abarbri, M. Abe, H. Abe, M. Abele, E.
Adachi, K. . Adams, .H. deAdger, B .J. Affandi, H. Ager, D.J. Aghade, B .B. Ahman, J. Ahmed, G. Ahn, J.H. n. IGfL Ahn, Y. Ahonen, M. Aihara, H. Aiqiao, M. Ait-Mohand, S. Aitken. R.A, Ajjou, A.N’A. adal41, Akai, s. Akane, N. Akasaka, M. Akazome, M. em. B, Akgtin, E. Akita, M. Akiyama, A. Akiyama, H. Akritopoulou, I. Akutagawa, S. Al Dulayym, J.B. Al-Masum, M. Alajarfn, M. Alami. M, Albanese, D.
391
262 245 069 112 106,232 147 349 062 381 290 247, 265, 270 382 313 286 184 172 382 047 320 113 013, 161, 181, 236 289 011,024 021, 038 035 016 188 003,239,240 187 006 194 255 316 131,307 15Q 169 006 142 072 315 267 222 375 375 240 179
Albaneze, J. Albouy, A. e. B, Alcantara, J. Alcaraz, L. Alcudia, F. Ales, C. Alexander, C.W. er. J, Alexander, IX. Allain, E. J. Allard, C. Allegretti, M. Allen, J.V. Almena, J. Alonso, M.S. er. H
Altamura, A. lvarez. C. Alvarez, S.G. Alvarez-Builla, J. Alvarez-Garcia, L.J. Aly, M.F. Amat, M. Amburgey, J. Amer. Amishiro, N. Amouroux. R An, D.K. Anand. R.C. Ananthan, S. Anceau, C. Andersh, B.
Andersson. C-M, Andersson. P.G, Ando, H. Ando. Andreasson, U. Andres, C.J. And&s, J.M. Andrews, D.M. Andrey, 0. Andrus. M.B.
318 010 144 375 036,222,280 296 365 087 030 382 163 081 154 015 120,254 329 008, 009, 072, 073, 084, 114, 149, 324, 383 204 048 136 242 360 144 303 225 050 216 328 013 260 390 148 363 070 323 337 247, 288,360 029 219 186, 188 292 017 230 146 151
392
A-B
Ang, K.H. Angara, G.J. Angers, P.
Anoune, N. Ansari, M.H. Antonioletti, Aoki, H. Aoki, Y. Aoyagi, Y.
R.
Appleton, J.E. Arai, M. Arai, s. Araki, M. Araki, S.
Araneo,s. Aranyos, A. Arata, K. Arcadi, A. Arcand, H.R. de. A.& Arienti, A. Arime, T. Arimura, T. Arista, L. Ada, A.
Amdt, S. Amecke, R. Aronica, L.A. Arora, A. Artaud, I. Arts, H.J. Asaka, K. Asaka, S. Asao, N. Askin, D. okan. C.V.
339 358 200 075 337 111 145 265 010 186, 343 009 274 260 003,053,335 121 067 270, 384 224, 268, 297, 301, 308 013,266, 319, 378 270 288 187 351 209 151,353 058 273 175 186 085 288 145 088 371 186,222 108 220 288 005 001 091 025, 253, 257, 289, 315, 375 288 286
Author Index
Aspinall, H.C. Astudillo, L. Atherton, J.I. Atherton, M. Atkinson, J.G. Attardo, G. Aube, J. Aubert, C. Aubrecht, K.B. Aurell, M.J. Austin, L.R. Avery, M.A. Awachat, M.M. Axenrod, T. Axon, J. Ay, M. vers. T&
Baba, Y.
Babu, B.R. Babudri, F. b
Rachiocchi. E, Bachki, A.
Backvall, J.-E.
e. D, Badparva, H. Bae, J.-Y. Baele, J. Baghel, S.S. Bahule, B .B. Baik. Bailey, P.L. B ailev. T.R Bailev. W.F. Baillargeon, M.M.
020 166 003 175 179 341 112 215 082 185 304 122 206 201 331 104 077 054
029, 202, 245 358 389 006 111, 377 027 327 174 305 179 064, 186, 360 080 101 069 124 180 356 136 096, 084 046, 175
095, 193, 237, 370
186,300,
094, 098, 188, 354,
266 213
Author Index
Bains, S. Baird, C.P. Bakker, B.H.
Baldino, C.M. Balducci, R. Ball, R.G. Ballestri, M. Ballini. R Balme, G. Balu, N, Bambridge, K. Banik, B .K. well. M.& Bao, W. Barba, F. Barbero, M. B arcina, J .O. Barco, A. Barden, M.C. Barks, J.M.
Barnhart, R.W. Baron, D.L. Barr, K.J. Bar-mud, J-Y. en. J.P, ett. A.G.M. Barrett, C. Barry, J.T. Barta, N.S. Bartels, B. Bartoletti, L.
393
113 159 222 389 006,052 283 163 348 238 299 113 183 178 205, 374, 335 338 124 047,060, 139 101 197 170 333 149 135 068,081, 250 035 343 067, 195, 342, 357, 190 179 051 311 180 246 286 073 301 262 370 038, 090, 256, 371, 386 011, 094, 330, 370,
ua. NC Baruah, B.
Baskaran, S. et, J& Basu, S. Batchelor, M.J.
386
135
355
318, 360
Bats, J-P. Baures, P.W. Bayguen, A.V. Bayston, D.J. BaIczewski, P.
Beaudet, I. Beaulieu, F. Beck, C. . eckwlu Beddoes, R.L. Bedekar, A.V. Bedeschi, P. Begley, M .J. Beg&, J.-P. Behnen, W. Behnke, M.L. Beholz, L.G. Bejan, E. e. cr.= Beletskaya, I.P. Belisle, C.M. Bell, K.E. Bellas-. M, ebM,
223, 382, 178, 385
Bellesia, F. Bellosta, V. Bellucci, C. Belotti, D. Belyk, K. Benaglia, M. Benati. Benazza, M. Bencheqroun, M.
390 304 063 331 013,039 356 356 293 199 002, 372,374 250 105 184 262 233 103, 104, 105, 121 264, 365 386 263 188 294 339 329 018 124 352 016 131 318 257 257 069 125, 201 117 219, 242, 285, 286 220 229, 328,343 053,244 322 244,295 278 111 135, 353 326 118
394
Bender, D.M. Benetti, S. Benguedach,A. Bennani, Y.L. Benneche,T. Bergens, S.H.
Bernabe, P. Bemad Jr., P.L. Bemad, P.L. Bernard, J.-M. Bernard-Henriet, C. Bemardi, G.L. Bemardinelli, G. . emmcz. m Bernstein, M.A. Berrang, B .D. Berrios-Peiia, N.G. Besancon, J. Bessho, IS. Besson, L. Betancor, C. Bethell, D. Bethmont, V. Beuchet, P. Beugehnans, R. fv-~. u.T, Bhamidipati, R.S. Bhandari, A. Bhar, S. s.v, Bhatia, B. B hatt, R.K. acharvvti Bhaumik, A. Bhushan, V. Bhuyan, P.J.
B
213 250 119 119 217, 251 103,256 062,070, 244 216 190 138,315 051, 265, 368, 371 134, 162 116 195 342 138 320 330 309 010 131 311 122 283 105 248 047,086, 222 321 217 229, 230 158 128 028 202 281 215 086, 330, 324 338 165, 295, 296, 336, 360, 362 020, 331 079, 118, 124, 127, 129 013 218 318
Author Index
. beniarz. C, Biermann, U. Bigi, E. Bigi, F. Bigot, A. Bijoy, P. Biles, C. B illeret, D. Billington, D.C.
Blacklock, T.J. Blagg, J. Blair, IA. Blart, E. Blass, B .E. mcher& S. B leicher, L. Blondeau, D. Blough, B .E. lum. J, Bobbitt, K.L. Boelens, M. Boersma, J. Boesten, W.H.J. Boeters, C. Boeykens, M. Boiteau, L. Boivin, J. oland. W, Balm. Bolton, G.L. Bomann, M.D. Bon, E. s. F, Boni, M. Bonini, B .F. . . onini. C, Bonne, F. Bonnet-Delpon, D. ooker-Milbum. K& Boons, G.-J.
029 344 105 330 058,062,254 028 060, 187 121 353 158 063 173 335 138 124 045 137, 378 167 364,374 002 353 122 065 261 124, 310 019 116,244 240 347 034 104 104, 118,123 218 031, 126, 151, 153,275,283 389 118 105 088, 093, 186, 223 328, 343 162 027, 267 118 352 185, 358,365
Author Index
Booth, S.E. Boothroud, S.R. chdt. R.T. Bordner, J. . ordolol. Bordoloi, M. Bosch, AI. Bosch., J. Bosco, M. Bose, AK. Bosica, G. Bosman, C. . osnrch. Bossard, F. ott. K Bouhlel, E. Boukherroub, R. Boulton, L.T. Boumizane, K. Bourdet, S. Bourgeois, M.L. Bourguignon, J.J. Bouvy, D. Bouyanzer, A. Bouyssi, D. Bouzide, A. . . ovrcellt. P, Bovonsombat, P. Bowden, N. owman. W.R Boyce, J.P. Boyce, R.S. Boyd, D.R. Bozee-Ogor, S. Brackeen, M.F. Brakta, M. Branan, B.M. Brandange, S. Brandes, B.D. Brasseur, D. Bratavanov, S. Brauman, J.I. Breedon, S.W. Brennan, J. Brenstrum, T.J. Breton, G.W.
395
256 137 243 252 034 363 115 303 090 101, 299 205, 374 081, 169 190 128 149-157 165 178 218 356 028 195 313 375 285 335 294,295 272, 382 357, 358 216 125, 126 075 263 231 120 116 238 077 263 191 163, 164 215 037 163 026 286 295 175,231
Breuilles, P. Bricout, H. Brieden, W. Brielmann, H.L. Briggs, A.D. . nmble. M.4 Brintzinger, H.H. Brittain, J. Brocca, D. Brochu, C. Brode, A. Broene, R.D. Town. H.C, Brown, J.D. Brown, S. Browne, M. Browning, A.F. Broxterman, Q.B. Bruce, M.A. Brummond, KM. Brumwell, J.E. Brunel, J.-M. Brunel, Y. Brunet. J.-J, Bruno, J.W, Brusotti, G. ee. J, Bruton, T.C. Buchwald. ST,
Bueno, A.B. ullo& R.M . umagm. N.A, ]3uonora. P.T, Bureau, R. Burws. K Burgess-Henry, J. Burley, I. 11.DA Bumell-Curty, Burnett, D.A. Bums, B.
C.
113 129 014 302 266 295, 298 221 246 244 098 301 073 040, 048, 136, 184, 235,249 195 213, 283 101 020 244 120 388, 389 383 231 239, 344 008, 132 152 020 016 136 026, 038, 051, 073, 123, 126, 130, 265, 287, 368,371 385 058 069 272 052, 194,306 039 042 032, 260 042, 158 300 362 100, 110 101 031
396
Bums, E.E. Bums, S.J. Butcher, J.W.
B uttle, L.A. Byrne, M.P. Byrne, N.E. Bzowej, E.I.
Caballero, G.M. Cabezas, J.A. Cablewski, T. Cabri. Cadamuro, S. z. G Cai, Z.-W. Cain, P.A. . Calabrese, J.C. Calkins, T.L. Callier, A.-C. Cameron, K.O. Campbell, R.A. Campi, E.M. C&npora, J. Campos Neves, AS. Camps, F. Canan Koch, S.S. Cancho, Y. Candiani, T. Cairo de Andrade, M.C. ononne, P, Cantrell Jr., W.R. Cantrill, A.A. Cao, Y.H. . vie&. P, Capdevila, A. Capella, L. Caplen, M.A.p
Capperucci, A.
B-C
132 352 195 013, 266, 319, 378 328 280 216 345 223
207 287 102 084 351,367 149 066, 199, 200, 222, 354 061 062 309 225, 388 074 105 346 165 301 099 027 354 145 320 084 033 200 033,096 109 008 303 046 353 101 238 167, 263 162, 198, 370
Author Index
Cardamone, R. Cardellicchio, C. Cardilli, A.
Carl&r, R.P. Carlsen, P.H.J. Carlson, J.A. oI& E. Caroon, J.M. Carpentier, J.-F.
Carreiio, M.C. etero. JC, Carreyre, H. Carter, D.S. Casas, R. Casolari, S. Castaiio, A.M. Castelijns, A.M. . i116n. S, Castle, G.H. Castro, P. Cativiela, C. Cave, A. Cave, C. . . . avlcchroni. G, Gazes. Celli, A.M. Cerezo, A. de F. . in. H, Cerreta, F. J& naboche, C. xii, w. nakraborty, R. . Jamberlin. A& bers. RJZ nampagne, P. nan. ban.
080 233, 234 223 293, 340 275 304 304 175, 262 033 099 124, 146 129 229,231 018 306, 385 381 145 122 051,061 063 018 011 185 288 284 317 349 043,046 063 230 321,322 313 081, 355 389 198 014, 048, 051, 053, 183 014 184 041, 269 145 175, 359 135 055 024, 350 226
Author Index
Chang, C.-J. Chang, S. Chang, S.W. Chany II, C.JH. Chao, H.-G. e. A& Charkraborty, R. Chatani, N. alogIu. C Chatterjee, A. Chatterjee, A.K. Chau, K. Chaudhary, A.G. Chauret, D.C. van. SP, Chavant, P.-Y. Cheeseright, T. Chemla, F. Chen, B.-L. Chen, D.W. en. F, Chen, H.-J. Chen, J-x. Chen, J. Chen, K.-L. Chen, L-F. Chen, L. Chen, L.-Y. Chen, P. . Chen, S.-H. Chen, S.-J. Chen, S.-M. hen. S.-T, Chen, S.-Y. Chen, T. Chen, T.-A. Chen, W-x en. W, Chen, X. n. Z-C, Chen, Z.-G. Chen, Z.-R.
397
013, 039, 107, 134, 324, 332 234, 281, 381 375 162, 353 014 102 010 097, 098,099 039 071, 074, 084, 216, 250, 374 178 127 009,044,055 200 299 026 082, 201 203 339 382, 385 156 205 205 300 198 094, 184, 218 390 042 200 101 289 172 237 110 055 110 110 290 067 198 184 017, 134, 151 204 025 224
hen, Z.C. Chen,Y.
Chem, C.-Y. Cherqaoui, M. Cheung, A.W. ChevaIlet,P. Chichaoui, I. Chida, N. Chini, M. Chisholm. M.H, Chiu, P. Chiu, R.-T. Chiummiento, L. ho. BT, Cho, C.M. Cho, C.S. Cho, H.-S. Cho, I.S. Cho, S.H. Cho, Y.-S. Cho, Y.H. ho. Y.& Choi, E.B. Choi, H.C. Choi, J. Choi, K.I. Choi, W.-B. ong. J.pvZ Chong, Y.H. Chono, N. Chordia, M.D. Chou, T.-S. hot&p. B.M Chow, E.K.F. Chuang. C.-P, Chuche, J. Chueh, L.L. Chung, C.K. Chung, J.-U. Chung, K.H. Chung, Y.K. Ciattini, P.G. nek. E, Cimarelli, C.
205 168 027 142 094 129 366 289 303 153 254 073 282 365 027 016 264,281 089 045, 083,234 072,073 101, 158 266 101 182 182, 226, 354 042, 205 026, 118, 135, 136, 161, 181 048 288 026, 301 325 108 356 066 154, 261 028 289, 332 003 373 106, 308 054 062 364, 371 335 106 256, 371
398
Cintas. Cintrat, J.-C. Citterio, A. Clader, J,W. Clark, D.N. k. J,& Clarkson, S. Clase, J.A. den. J, Clegg, W. Clement, J.-C. Clerici, A. Clerici, L. Cl&y, P. Clinet, J.C. Coats, S .J. Coe, D.M. oe. J.W, ohen. T, Colandrea, V.J. Colbert, J.C. oldha. L Cole, B .M. oIe. DC, Collado. I.& 0. I& Collin. J, Collington, E.W. s. s, Collis, A.J.
Colomb, M. olol&o. L Comina, P. J. . omrns. DL Concellb, J.M. Conception, A.B. Condit, F.H. Condon-Gm Conggui, Y. Congreve, M.S. Conte, V. Contento, M.
Author Index
111 025 264 305 058, 296, 345, 351 101 126 314, 344 213, 283 021,022,099 096 026 256, 270 256 199,200, 354 160 333, 348 233 050,072 011, 024, 354 238 224 128, 319, 321 372 243 329 172, 218 029, 257, 286 230 258 321 163 067, 082 269 020 190,218 295 195, 342, 357 019, 159,200 388 093 157 043 174 309
Cook, K.L. Jr.. U Cooney, J.J.A. Cooper, M.A. Coote, S.J Cop&et, C. orev. FL
.
ormrer. JE Cornwall, M.J.
Costa, A.L. Coudert, G. Coumbe, T. Courtemanche, G. Cowell, J.K. Cox, G.G. Cozzi. Craig, S .L. Crane, KM. Crasto, C. Crawford, K.B. Creton, I. Crich. Crispino, G.A. Crotti. Crousse, B. we. W.F, Crowley, P.J. Cruciani, P. Crump, R.A.N.C. Csiba, M.A. Cuerva, J.M. Cui, D.-M.
332, 359 090,111 099 264, 310 126 126 302, 340 087, 157, 248, 264,274,285 042 029 357 209 077 002 010, 053, 199, 244, 294, 295, 310, 345,358 015, 018 148 133 066,081 217 297 185 326 111 322 073 175 253 209 274 215 194 366, 373 109 246 254,256,271 240 216,224 088 215 092 050 385 185 241
Author Index
Cuny, G.D. Curci. c Cusack, K.P.
D’Accol ti, L. d’Angelo, J. D’Aniello, F.
D’Auria, M. Dack, K.N. Dahl, S. Dai, L. Dale, C.M. DaIlavaIle, S. Dambrin, V. Dan, L. Dang, H.-S. Dang, Y. er. a Danhui, Y. Daniel, T. Danishefsky. S.J, Das, A.R. Das, B.C. Das, J.
Datar, R. Date, T. Datta, A. Dauphin, G. Daus, K.A. aves Jr.. Ga Davey, CL. Davies, H .M. . awes. H Davies, I.W. Davis, F.A. Davison, E.C. De Buyck, L.F.
C-D
287 204,267,268 107 177 337
267, 063 353 081, 169, 343 121 171 272 030, 222 229, 128 381 211 082 205 074 185 174, 275 037 123 332 013 023, 168, 133 089 387 148 175 077 384 390 095, 083, 386 043 273
268
107, 154, 355
322 231
270
363 308
096, 339 318
399
.
e Krmne. N, De la Torre, J.A. . e MICO. k De Rijk, T.C. De Risi, C. De Sarlo, F. De Simone, A. De Smaele, D. De Wit, D. de Dios, A. de Faria, A.R. de la Cruz, P. . e la Pra R-F, de la SaIud, R. de Marigorta, E.M. de Meijere, A. de MenorvaI, L.C. de Sousa, J.D.F. de Vries, E.F.J. Deaton, M.V. Deberly, A. em Decosta, D.L. Dedopoulou, D. Deeani. . erllk& Degnan, A.P. de1 Campo, C. de1 Pozo Losada, C. de1 Villar, A. Delair, P. Delaude, L. Delauna y, J. Delgado. A, Delgado, F. Delougu, G. Delplancke, J.-L. Dedllv. Cr, Deng, L. Dew. M.-Z, Deniau, E. Denis, R.C. Denmark. S .E, DePue, J.S. Derien, S.
122, 124, 125, 310, 321,347 299 349 273 250 228 340 125, 321 273 387 357 115 074, 387 143 212 339, 378 168 134 016 351 034 095, 269 252 366 149 162,198,370 313 241 318 064 167 049 390 320, 354 048, 205 020 023 326 163 077 297 097 126, 168, 225, 233 168 038,286
400
des Abbayes, H. Deschoux, L.
Destabel, C. Detomaso, A. Devan, B. Devasagayaraj, A. Devi, T.R. Dexter, A.F. Dhanabalasingam, B.
Dhokte, U.P. Di Bussolo, V. . . 1 Funa. F, Di Martino, E. Di Martino, J.-L. Diaz, M.J. Diaz, M.D. Didiuk, M.T.
Diez, B .R. Diez-Barra, E. DiGiacomo, M.
Dinesh, C.U. Ding, S. Ding, Z.B. Discordia, R.P. Diter, P.
Doecke, C.W. Dogan, 0. Domalski, M. Dominguez, E. Dong, T.-W. Dopico, P.G. Dorey, G. Doris.
D-E
026 221 080 229 221 267, 278 070, 372 165 248 306 086 040 271 174 293 112 052 304 258 040, 087, 133 068 115 020 035, 037
268
Author Index
Domer, W. Dorr, H. Dorsch, D. Dorm, R.L. Doty, M.J. Doubleday, W.W. OlQJJ&
195, 203 Downing,
S.
Draper, T.L.
279, 322 128, 132,
118
027, 076, 078, 279 206 221, 278 231 252 028, 221, 278 286 181 104 101 381 086, 137 376 158 221, 269
Dreisbach, C. Dreyer, G. Du, H. Duan, J.-P. Duan, J.-X. ubac. Dubois, P. Dubree, H.J.P. uw. A G Ducoux, J.-P. Duetsch, J. Duetsch, M. Duffy, D.E. Duffy, J.L. Dugar, S. Dughera, S.
Dullweber, U.
Duncan Jr., S. Dunigan, J.M. Dupuis, C. Durant, A. Duthaler. R.0, Duttachowdhury,
EaIlah, A. Eastwood, F.W. n. BE.
SK
078 192 260 217, 292 367 024 067, 083,200, 204, 210 113 054, 108 028 068 084 011 034 350 103 027 172 172,357 095 051 069, 245, 264, 365 278 109 231 388 385 101 149 285 285, 344 263 007, 029, 036, 038, 152, 160 076 138 129 023 243 127
105 310 317, 267
Author Index
Ebel, M. Eby, P.
Edwards, A.J. Edwards, J.O. Edwards, L.G. Eggleston, D.S. Eguchi, K. Eguchi, M. Eichelmann, H. Einhom, C. Einhom, J. Eisenberg, C. Ekinaka, T. El El Anzi, A. El Arabi Aouad, M. El Meslouti, A. El-Subbagh, H. Elder, M. Ellestad, K.E. Elmalak, 0. v. s.s, Enami, H.
E-F
095 050 185, 287 129 299 204 203 105 177 290 228 185 185 014, 278 220 008,009, 114 326 263 263 381 031 389 065 006 376 218
288 089, 272, 273, 333 Enkelmann, V. Epa, W.R. Ericsson, A. Ericsson, A.M. Escribano, A. Eshelby, J.J. Boenson. J.K Ethiraj, KS.
361 352 354 098 306 088 184 082
Evans, G.R.
032,040,297 336 112, 373, 390 242, 306
Fabre, A. Fabre tti, A. Fache, F. Fahndrich, B.
401
Falck. J.&
Fallah, A. Failer. J.W, . alhs. A.Ct Familoni, O.B. J-M, Fang, L. Fang, W. Fantin, G. Farina, V. Farinola, G.M. Farthing, C.N. Favero, L. Federici, C. Feixas, J. Feldberg, L. Felder, M. eldd eldman. K& Felix, D. Felix, C.P. Feltman, T.L. Feng, F. Ferguson, M.D. . inga. BL. Fermin, M.C. Femanandez-Acebes, A. Femandez, M. Femandez, E. Femandez, I. FemSldez, R. Ferrara, M.C. Ferreri, C. Ferri, F. Feuerer, A. . Kin-.
v.
020, 036, 045, 083, 222, 234, 280, 331,381 103 350 130 068 245, 375 186 117 189 222 084 299 254,256,271 027 046 332 031, 126 225 250 280 312 076 379 113 151,341 152 304 299 284 143, 296 208 162 178 240 347 084, 111, 186,
233, 234,300, 377 Fields, J.D. re. B,
267 230 073, 104, 158
Figueras, F. .. . .
099
Finney, N.S.
111pn1n1. . lnn.
IA,
M.G,
231 014, 043, 046, 199, 354 349 316 376 309
402
Author Index
Fioravan ti, S . Fischer, H. er. G&
Fitch, R.W. Fitzgerald, J.F. Fitzgerald, J.J. Fleming, F.F.
lemming,
S,
Fletcher, R.J. Florez, J. Fochi. Fogagnolo, M. J.-C, my. JALfi, Folmer, J.J. Fong, S .F. Fontenas, C. Forbes, D.C. Forbes, J.E. Forcellese, M.L. ortes. C.C. Fotuhi, L. Foubelo, F. 0uQyet. E, Fowler, C.B. Fowler, K.W. Fowley, L.A. Fox, D.N.A. Fraile, J.M. Francisco, C.G. Franck, X. Franzosi, G. Frechou, C. Freskos, J. Fried, C.A. Fried, J .A.
133 007, 101 220 025, 119, 136, 255, 321 138 146 255 368 117 147, 375 043, 05 1, 092, 212 089, 091, 092, 093 130 051,061, 124 067 149 189 184 312 140 226 257 168 104 205 093 237 265 120, 174, 251, 254 118, 336 132 121 073 257 257 312 168, 349 292 014,043,046 229 326 105 122 258
Frost, C.G.
Fu, G.C. . . T, uchmr. Fuchikami. T, Fuchs, K. Fuchs. P.L, Fuest, M. Fugami, K. Fuhry, M.A.M. Fuji, K. Fujieda, Y. Fujii, A. Fujii, H. Fujii, N. Fujii, T. Fujimori, C. Fujimoto, K. Fuj imoto, T. Fujimoto, S. Fuj ioka, H. sawa. T, Fujita, H. Fuji@ K. Fujita, S. Fujiwara, K. Fujiwara, T. .. finwara. Y,
Fuk, D.-K. Fukui, H. Fukui, S. Fukumoto, Y.
Fukuyo, E.
359 049 229 015 132 214 223, 224,249 292 012 346 105, 233, 389, 390 079 019,080,298 043 055 226 033,035, 348 251 003 063, 172, 380 291 030 254 376 194 304 127, 277 017 342 084 029 281 003, 134, 135, 201, 248, 347, 362 219 315 342 074, 250 007, 376 134 041 018, 155,202 259, 271 022
Author Index
Fuller, J.C. Funahashi, Funakoshi, Funawashi, Funicello,
M. K. M. M.
Furet, N. f+lBJUA Furuhashi, K. awa. L Furuta, K. Furutani, H. Fusco, C. ro. S,
Gabel, C.J. Gabriel, A. Gabriel, A.O. Gac, T.S.
F-G
025, 125 361 189 274 027 368, 199, 119, 300 379 380 269, 265 267, 304
035, 119,
389 345, 358 120, 195,
279 268
Gag&, M.R. Gagnon, J.L. Gai, Y. s. H.-J. Gajda, C. Gakb, R.H. Gala& P, 0. A& Gallagher, T. Galpin, J.D. em. B, Ganeshpure, P.A. Ganin, E. Gao, C. Gao, J. Gao, Q. c Garafalo, L.M. Garavelas, A. Garbaccio, R.M. Garcia Ruano, J.L.G.
002 336 340 158 127 032 193 226 228 277 329 343 166 318 192 119 205 050 074 198 269, 279 032, 322 330 158 157 306
Garcia,B. Garcia, J.I. Garcia, M.
403
Garcia,0. Garofalo, A.W. Garro-Helion, F. Garrote, C.F.D. Garroust, P. Gasch, C. Gaspard-IIoughmane, sman. PG. Gatti, R.G.P. Gaul, M.D. Gebehenne, C. Geib, S.J. Geirsson. J ,m Gelber, N. Genba, A. Geng, B. Genin, M.J. Gentilucci, L. George, M.V. Geraci, L.S. Gerardin-Charbonnier, Geri, R. Gerold, A.
Gervat,S.
H.
C.
048 040, 246 104 154 138 2377 289 208 172, 357 352 360 121 038,239 204 384 331 307 110, 129, 033, 137, 138,378 077, 280 121 293, 308 168, 308 014,015 2 17 238 092
311
Ghodeshwar, S .B . Ghorai, M.M. hose& Ghosh, A. Ghosh, A.C. Ghosh, U. Giacomini, D. Giammaruco, M. Gibson, F.S. Giesen, V. Giffels, G. wte. B,
293 247 229, 230, 328, 343 211 091 114 115 055, 390 051 309 316 138 079 034 145
143
Gilbert, A.M.
221
168, 349 241
Gilbert, B.A. Gill, G.B.
375 200
Gevert, 0. helfi. F,
Author Index
Gillard, J.W. Gillespie,
R.J. . Gimisis, T. Gioanola, M. Giovagnoli, D. Giovannini, P.P. Giovannini, R. Girard, Y. Girija, K. Giroux, A. . . anmr. A.& Gladstone, B .G. s. &s, Gluchowski, C. Gnappi, G. Gnecco, D. Goda, K. ev Jr.. JD, Godfrey, A.G. Goh, J.B. Gohain, S. Gokhale, A.S. let. J.M.(Z Gomez Pardo, D. G6mez-Bengoa, E. Gono, J. ves. A&Id IkB, Gonzalex, J.M. Gonz&lez, A.G. Goodall, K. Gopal, D.
or& J, Gosmini, C. Goti. Goto, Y. Gotoh, N. Goulaouic-Dubois, Gould, A.E. Goux, C. Grabowska, U. Graf, R. Graham, A.E.
C.
341 127 293 276 178 128 309 189 202, 179 199 359 123 279 230 306 058 123 068, 238 119 271 137 150 293 010 287 148 167 360 166 290 090 141 025, 125, 321, 239 125, 019 007 136 074 160 105 199 229
Gralek, J. Grandclaudon, P. Grandi, M.
386
069, ,081
Gmndjean, D. Grassl, Y .N. , Graven, A. Gravestock, M.B. Gray, J.L. Green, A.D. reen. J.R Green, N.J. Greenhall, M.P. Grellier, M. Grice, P. Gridnev, I.D. Griebenow, N. co. PA Griedel, B .D. Griengl, Grier, M.C. Grigrr. Grijzen, Y. Grimaldi, J .R. Grison, C. ssom. J.W. Grivas, S. Grogan, M.J. Grossman, R.B.
035, 119, 255 322, 335 228
Grove, D.M. r&bs. R&. Grushin, V.V. Gu, D. Guan, C. Guan, L. Guan, X. Guch, I.C. Guerreiro, P. GueKero. A, Guertin, K.R. Guesnet, J.-L.
285 297 062 230 003, 180 258 097,33 1 171 117 366 121 361 147 359 020 125 352 251 121,351 233 274 014 202, 203, 212, 213, 283 308 320 217 059, 074,227 120 248 207 368, 371 346, 371 064 216, 223,224 009 227 205 348 243 383 035, 118 033 046 228 070, 244
Author Index
Gueugnot, S. Guha, M. Guib& F. Guijarro, A. Guijarro, D. Guillemont, J. Guise, L.E. Guishu, Y. Guisnet, M. Gulevich, Y.V. Gundersen, L-L. Guo, C. Guram, A.S. Gurr, P.A. Gusmeroli, M. ec Jr.. F& Guzzi, U. Gyoung, Y .S.
Haaima, G. Habaue, S. Habi, A. Hache, B. Hachiya, I.
Hada, W.A. Haddad, N. Haddon, H.A. Hadida, S. r. u Hahn, J.-T. Hahn, P. Hai, A.K.M.A. Haigh, D. Hajra, S. Hamada, T. Hamaguchi, F. Hamamoto, M. Hamaoka, S.
Hammadi, M. Hammaker, J.
G-H
240 310 138 247, 262, 276 020,039,099 148 344 373 016 145 077 350 037, 337, 369 130 102 316 172, 218 080 048
327 022, 380 331 040 018, 197, 224, 268, 270, 297, 301, 308 127 197 257 303 163, 165 136 207 297 326 091 164 290 166 100 179 112, 305, 312, 350 196,273 124
Han, Han, Han, Han,
J.L. S.-M. W. Y.
Hanaki, N. Hanamoto, T. Hananki, N. Hanaoka, H. Hanaoka, T.-a. del. H, Handke, G. Haning, H. Hansen, K.B. Hanson, M.V. Hanzawa, Y. Hara, R. Harada, K. c Harayama, H. Hardcastle, I.R. Hardee, J.R. . inger. S.& Harigaya, Y. Harimoto, T. Harlow, R.L. Hamett, J.J. Harper, S. Harper, T.G.P. . Harris Jr., G.D. Harris, B.D. Harris, C.E. Harris, L.J. Harris, M.C.J. Harrison, J. Harrity, J.P.A. Hartner Jr., F.W.
Harvey, I.W. Harvey, J .N. Harwood, L.M. e. T, Hasegawa, A.
136 187 386 021, 186, 237, 275 274, 346 245, 379 268 267,268 150 120 088 199 309 093, 195 043, 256 380 023, 322 235 298 053 331 042 142 254 106 036, 222,280 207 263 032, 260 227 298 112 192 185 124 025,035, 119 363 288 130 191 353 389 378 338 219 266
406
Hasegawa, H. Hasegawa, M. Hasegawa, T. Hasha, D.L. Hashiguchi, S. Hashimo to, M . Hashimoto, N.
Hashiyama, T. Hata, E. Hatajima, T. evama. S, Hatakeyama, T. mnaka,
Author Index
H
Y,
Hatano, K. Hatano, T. Hatayama, A. tern. J.M, Hatfield, L.D. Hauck, S.I. Hau tefaye, P. Havcnnith, R.W.A. Hay, B.A. Hay, L.A. Hayakawa, S. Uayashi. A, Hayashi, C. Hayashi, H. Hayashi, M. . avashl. T,
I-Iayashi, Y. Hayashikoshi, Hayn, M. Hays, D.S.
T.
He, D.-H. ock. C&., Hebri, H. t. s.m Hedgecock, C.J.R. Heer, J.P.
302 052,062 196, 376 255 033 367 241 201, 303, 020, 062, 323 247 390 324 159 174 331 068, 069, 081, 378 029 255 169 320 138 302 250 019 230 181 361 283, 368, 034 266 001, 260, 034, 041, 220, 243, 271 236 147 274 168, 249 356 012 298, 366 036, 152 209 293 230
330 128,
de. S.G, Hegde, V.R. Hegeman, A.D. Heid, R.M. HelaI, C.J. Helgason, A.L. Helland, I. Hellberg, L.H. Helton, E.S. . en&&on. Menin, Henry, J.R. H&ion, H. Hermans, B. Herr, R.J.
070, Hewawiism.
P,
Hewkin, C.T.
369
291 077, 261,
L Hibino, H. Hida, K. fIidai, M, Hiemstrd Higashiura, S. Higashizima, T. Hightower, T.R. Higuchi, S. Hikichi, K. Hill, D.H. Hillers, S. Him& Y. Hindley, R.M. Hinkle, K.W. Hino, F. Hioki. H, Hioki, K. Hirade, T. Hirai, K. Hirai, N. Hirama, M. Hirano, K. Hirano, M. Hirao, K.
071 205 209 353 157 074 175 171 132 122 176 l30, 188 009 239 081 298, 319 136,334 081 294 096 300 377, 380 086 074 116,291, 329 155 054 207, 336 091 001 069 161 331 326 022 115 060, 252 224, 236 302 259 186, 188 241, 283, 368, 369 327, 337 007, 143, 230, 376 loo
Author Index
Hirao. Hiraoka, M. Hirashima, T. Hirata, K. Hirosawa, C. Hirose, Y.
Ho, P.T. Hodgson, P.B. Hoegy, S.E. Hoem, A.B. Hoffmann, G. Hofle, G. Hojo, M. Holland, H.L. es. a Holmgren, E. Holoboski, M.A. Homma, K. on. Y.-S, Honda,Y. Hondo, T. J.-fL J.-I, Hong, R.-K. Hong, W.S. Hong, Y. Hoover, D.J. Horan, N.R. Horiguchi, I. Horiguchi, K. Horiguchi, Y. Horikawa, Y. . . mchl. C.h, Horiuchi, M. Hormuth, S. Horsburgh, C.E.R. Hoshi, K. Hoshimi, II. . osbo. 0, Hosokawa, H.
407
H
063, 337 376 061 062 106 160, 005, 070, 378 247 190, 314 314 209 104 273 079 050, 035, 231 043 191 364 182 133 311 091 283 161 281 182 032, 127 040 079 160 345 281 344, 223 260 003 103 291 017 344
165, 172, Hosoya, N. Hosoya, T.
380 068, 069, 081, 292,
Houminer, Y. Houpis, I.N. Houri, A.F. Houser, J.H. oveda. GK,
214, 218
067 325, 348
Howson, W. ave. T.R Hoying, R.C. rubv. V.J. Hsieh, L.-C. u. C.-N Hu, M-Y. Hu, W.-X. Hua, Y. Huang, Huang, Huang, Huang,
258
360
J-L. J. S. W.-H.
Huang, Z.-Z. Huby, N.J.S. z Huffman, M.A. Hufton, R. Hug, M. Hug, R. Hughes, K.A. Huglin, J.A. Huhn, T. Hui, R.C. Hunter. R, Hupperts, A. Hur, C.U. Hussonin, Md.S. Hutcheson, D.K.
035, 325, 169, 196 097, 322 338 087 040 339 040, 322 109 274, 138 087 360, 094, 198 172 067 237 114 236 335 373 155 156, 021, 186, 282, 340 096 154 368 128 166 291 376 197 346 268 065, 119, 337 176 095
091, 192, 348 231 285
247, 279, 367
371 174
335, 340 077, 098, 236, 275, 340
262, 347 120
408
Hutchinson, J. Huttenloch, M.E. J.R HuvaI, CC. Hwang, S.H. wu. J.R
IMiiez, P.L. Ibers, J.A. Ichikawa, S. Ida, T. Jgnatchenko. A.V, Ignatenko, A.V. Ihle, N.C. Ii, N. Iida, H. Iida, Y. Ikariya, T. Ikeda, E. Ike I.
Ikeuchi, Y. IlaH. Ilankumaran, P. Imada, Y. a. K, Imai, A. Imai, N. Imai, R. Imai. Imai. to. T, Imanaka, T. Imashiro, Imi, K. Imoto, H. Inagaki, A. Indolese, A. Indolese, A.F.
H-I
052,137 359 221 390 065 371 149, 156, 373, 375 315 163 005 074 106 346 366 372 303 073, 262 033,036 165 108 091,241 201,330 256 198, 265 107, 134 110, 155, 237 163, 164, 165, 231 378 097 194 019 021 324 152, 153 331 083, 388 092 035 061 245, 379 377 369, 379
Author Index
Ingrum, A.I. Inokuchi, T. omata. Inoue, H. Inoue. S, Inoue, T. oue. Y, Ipatkin, V.V. J,
noor. N, Irie, R. Isaac, M.B. Jshibashi. H, Ishibashi, N. Ishibashi, T. Ishichi, Y. Ishida. Ishifune, M. Ishihara, K.
.
thara. T, Ishii, M. Ishii. Y,
Ishikawa, T. Ishimi, M. Ishino, Y. Ishitani, H. Ishiwata, A. Ishiyama, T. Ishizaki, M. Ishizuka, T. Isobe, K. be. M, e. S, Isono, N. Issac, M.B. Itaya, T. Ito, H. Ito, K. Ito, s.
071 152 149 019, 140 091, 274 148, 260, 327 012, 033, 338 346 101, 165, 187, 188, 190, 191, 295, 296, 336, 360, 362 157, 263,265 164, 169,231 024 108, 372 325, 348 232 272 182 036, 194 032, 268, 269, 274, 279,346 266 292 074, 144, 152, 166, 189, 197, 255, 266, 324, 347, 362,367 143 176 148, 332 224,268, 297, 301, 308, 314 355 195 017 354 361
238 054,272, 370 089,278 042 196 043, 253,256 094 166
Author Index
It& s. Itoh, A. Itoh, D. Itoh, K Itoh, T. Iwahama, T. Iwama, T. Iwamura, H. Iwasaki, K. Iwasaki, M. Iwasawa, N. er. S, Iyer, V.S. Izumi, J. Izumi. Izutsu,M.
Jaber, M.
Jacobs, V.A. n. EN, en. E.W Jacquault, P Jacquot, L. Jagtap, S.R. Jahn, U. Jain, N.F. Jain, R. Jakaki, J.-i. James, B. Janaki, S. Janardhanam, s. Jang, D.O. Jang, S.-B. Janosi, A. Janousek, 2. Janssen, E.
409
135,335 001, 042, 271, 376 060, 144, 316 160 091 292 246 189, 197, 107, 192, 220 143 074 183, 361 036, 189 361 146 305 115
253, 252,
362 386
144 096, 266 301 302 320 162, 163, 164, 165, 309 353 007, 112 293, 357 104 047,211 118 157 296 032 087 213 278 071, 336 178 024 239 306, 365, 375 119
Jarosinski, M.A. Jaspars, M. Jasperse, C.P. Jastrezebski, T.B.H. . zbm. J.& Jayasinghe, L.Y. Jean, T.-S. Jeffery. T, d. CW, Jenkins, T.J. Jenner. G, Jennings. W.B c Jeong, K.-S. Jeong, N, Jeoung, M.K. Jestin, J.-L. Ji, J. Jiaang, W-T. Jiang, J. Jiang, S. Jiang, W. Jin, J. Jin, L. Jin, S.-J. Jin, 2. Joglekar, B .R. Job. T. Johannsen, M. Johnson, J.R. Johnstone. R.A.W, Jolie, R. Joo, B.J. Joung, M.J.
Joseph, R. Joseph, S .P. Josien, H. Jouannetaud, M.-P. da. M, Jouglet, B. Joullie, M .M. Jourdain, F. Joumet, M. Jubert, C.
087 039 093 288 011, 094, 330, 385, 178 258 365 076,079 307 362 308 231 246 364, 371 051,053 215 002, 093, 328, 353 161 137 290, 306, 326 183 236 226 319 389 353 084, 100 133 287 167 321 308 236 133, 168,309 171 169, 172, 193 294 107 357 306 252 137 306 082 066
410
Julia. Jumnah, R. Jun, P. Jun, W.S. Jun, Y.M. Jung, J.C. Jung, K.-Y. Jung, L. Jung, Y.S. Junga, H.
Jurata, H. Juroboshi, M.
Juteau, H. Kabalka. G.W. Kabayashi, Y.
Kablaoui, N.M. Kaczmarek, I;. Kadoata, I. Kagawa, M. Kageyama, M. Kagoshima, H. Kai, A. Kai, 0. Kakehi, A. Kakinami, T. Kakiuchi, F. Kakiuchi, T. Kakuda, H. Kalberg, C. Kalberg, C.S. Kalinin, A.V. . ahvretenos. A.G, Kalra, S.J.S. Kaltia, S . c Karnatani, A.
J-K
021, 022, 099, 226, 382, 385 305 157 048 104 042 054,083 095,291 312 364, 374 198, 265 094 220 070 100 068 097
008, 012, 113 371 089, 091, 093 038 113 315 231, 246, 117 380 020,062 128 144 303 073 071,084, 096 032 260 108 313 188, 190 219 303 071
Author Index
Kambe, N. Kameoka, C. Kameyama, A. Kami, M. Kamphuis, J. Kanai, T. Kanamori, M. Kanazaki, M. Kanda, T. Kandzia, C. Kaneko, M. Kaneko, Y. ema.S, Kaneta, N.
030, Kang, T.S. 092,
269
374
Kanth, J.V.B. Kao, T. Kapoor, K.K. mtein. B, Karam, 0. Karanewsky, D.S. Karasawa, T. Karthikeyan, M. Kasai, K. Kasar, R.A Kasatkin, A. 44 KashimuS. Kashiwagi, H. Kashiwagi, K. Kassim, A.M. Kassir, J.M. Kataoka, M. woka. T, Kataoka, Y. Katayama, Y.
284, 286 108 329 304 012, 123 244 271 344 152 092 167 152, 153 317 159, 248, 251, 259 252 001,278 182 017, 146 024, 054, 083, 187, 276, 281, 283 308 043, 044,057, 217 122, 127 184 349 116, 244,291, 329 357 116 277 199 081, 377 364 023, 024,098 192 090, 194 160 261 071 059, 366 246 107, 192,386 072, 135,326 347
Author Index
Kato, A. Kato, H. 0. s, Kato, T. Katoh, T. v. A&
Katsuhira, T. . 1. 13,
Kaur, D. Kaur, G. Kawada, M. Kawaguchi, M. Kawahara, T. Kawai. Kawakami, J. Kawamura, K. Kawamura, T. Kawamura, Y. Kawano, N. Kawano, T. Kawasaki, I. Kawasaki, K. Kawase, T. Kawasoe, S. Kawasuji, T. Keavey, K.N.
Kee, I.S. Kelkar, S.V. Keller, J .L. Kemp, D.S. Kemp, M.I. de. & Kennedy, K.E. Kennedy, R.M. Kennewell, P. Keo, E.A. Keong, P.-H.
411
224 376 092 372 009 008, 106, 112, 125, 172, 190, 334,373 235 094, 151, 164, 169, 231 221 194 086 345 197 178,261 100 290 086,259 284 236 216 060, 144 291 253 262 151 220 049, 144 067,259, 325 242 249 014, 015, 017, 087, 102, 226, 253 323 201 288 072 126 167, 210,228 206 263 212 085 282
Kepler, K.D. Keppens, M.A.
Kessat, A. Keusenkothen, Khalil, H.
P.F.
Khatimi, N. Khiar. Khim, S.K. Khire, U.R. Khumtaveepom, K. J.M Kiddle, J.J. Kido, Y. Kiers, N.H. Kiguchi, T. Kihara, N. Kikuchi, S. Kilbum, J.D. Kim, B.H. Kim, B.T. Kim, C.S. Kim, Kim, Kim, Kim, Kim, Kim, Kim, Kim, Kim, Kim, Kim.
E.G. E.J. H.R. J.I. J.M. J.N. K. M.H. N. O.K.
Kim, Kim, Kim, Kim, Kim, . im.
S.-H. S.W. S.Y. T.-H. W.-S. Y.H,
Kim, Y.S. Kimura, F.
175 122 137 363 358 106 202 055 312 296 313 235 149 249 389 259 341 254 062 324 221 136 226 313 071 387 118 014,051 132 017, 146 051,053,183 062, 116, 132 277 307 016 183 023, 264,281, 323, 325,351 023, 216,224 348 337 054,083 382 042,205, 334, 386 348 092
K
412
Kimura, M. Kimura, S. Kimura, T. King II, R.M. King, S.B. Kini, A.D. v. w.q, Kinoshita, A. Kinoshita, H. Kinter, K.S. Kinugasa, H. Kiplinger, J. Kirihara, M. Kiril, M. . . imichg&o.
029, 149, 298, 302 383 226, 240 173 247 214 077 321 149 333 376 252
SV,
Kirschberg, T. Kise, N. elvov. A.S. Kishida, M. Kita, I. Kita. Kitagaki, Kitagawa, Kitagawa, Kitagawa, Kitaichi, Kitamura,
S. H. K. 0. K. M.
Kitano, K. Kitayama, K. Kitmura, T. Kivooka. S, Kiyota, M. Kizaki, H. Kleijn, H. Kleiner, K. Klement, I. Klempier, N. Klettke, F.W. Klinekole III, B .W. Klingberg, D. Klug, P. Kluge, R.
130 157 201 254,299 107, 191, 312 025 192 161, 194, 291, 342 194 185 262 148, 327 045 245 156 159 041 061 159, 248, 251, 259 329 195 288 148 209 274 321 104 059 247 273 318
Author Index
Knecht, M. Knight, J.
..
nolker. H.-J, Ko, H.-H. Ko, J.-A. Ko, S.-B. Kobatake, T. Kobayashi, N. . obw
.
obayashr. Y * Kocovsky, P. Kochanewyczm, Kodoi, K. Koenig, T.M. Koga, G. Koga, K. Koh, H.Y. Koh, Y.J. Kohler, T. Kohno, Y. Koide, T. Kolb, H.C. Komiya, N. . omi& Komori, T. Konda, Y. Kondaiah, P. Kondakov, D.Y. Kondo, K,
M.J.
102, 300 218 117, 221 113 014, 066, 184, 209, 355 199 374 266 107 077 007, 018, 197, 259, 270, 280, 308, 064, 142 231 386 339 069 181 029, 355 076, 182 386 371 085 177 246, 151, 007, 338 142 143 078, 215, 356
103, 116,
343 016, 040, 070,078, 195, 203, 222, 278,
128 022, 097, 224, 226, 267, 268, 273, 277, 297, 301, 314,325 348,380
148, 149, 147
250 166 376
083, 212, 379,380
Author Index
413
Kondo, M. 0. s, Kondo, T. Kondo, Y. Kong, M.S. Kono, K. Koo, B.-A. Koprowski, M. Korda, A. Kordik, C.P. Kore, A.R. Kos tova, K. . osugl. M& Kotian, K. Kotora, M. Kovalev, I.P. Koyama, K. Kozai, I. Kragl, U.
Krebs, A. Kreif. Krishna, A. Krishnamurthy, Krishnamurthy, Krishnan, K.
D. V.
Krowiak, S.A. Kruahong, T. 0. PL E-use, C.G. Kshirsagar, S.N. 4 Kubo, Y. Kubota, H. Kubota, Y. Kudo, H. Kudo, T. Kiihlein, K. . WCS. Fti Kukuma, T. Kukuzawa, S.i. Kulasegaram, S.
194 049, 144 131, 307, 311, 339 030,065, 324 387 387 236 364 266 234 290 087 186 037 240 191 081, 377, 380 246 346 341, 380 232 034 090, 207, 363 088,092 242 095 199 014,017 267 369 231 344 358 175 016, 129 060 056 221 147 150,315,334 230 012, 123 220 349 024 032 194
.
awiec. u Kum, P.W.Y. Kumar, A. Kumar, J.S.D. Kumar, K.A. Kumar, K.S.R.
Kumareswaran, R. Kumobayashi, H. Kunath, A. Kundu, M.K. Kunisada, H. Kunishima, M. Kunitake, K. Kuniyasu, H. Kuno, T. Wats.
Kurihara, A. Kuriyama, Y.
Kurosawa, S. Kurozumi, S. Kurth, J.A. Kurumizawa, Kurusu, Y.
S.
Kusama, H. Kusuda, S. Kusui, H. moto. T, Kuwabara, T. .. uwm Kwochka, W.R. Kwon, 0.0. Kwon, S.Y.
049, 194,369 028 028, 278 308 360 039 044,056,205 169 203, 387 267 148 338 278 049,144 224, 236, 388 376 051 049 248, 362 141 052 166,207 196 292, 378 385 175 177 385 385 148 025, 117, 348, 363, 372 114, 115, 198, 314 236 255 005 196 020, 267, 319, 345 177 014, 051,053, 183 014
L
Labiad, B. Labrouillere, M. Lacy, D.B. Lafontaine, J.A. Lagu, B .R. Lai, G. Lai. Lakner, F.J. Lakshmaiah, G. Lamidey, A-M. Lampariello, L.R. LaMunyon, D.H. s. Y, Landi Jr., J.J. c Langer, F. .
1s. Y, Lam&i, P. Lantos, I. Lara v. Lardicci, L.
ock. R.c
Larouche, D.
Latini, D. Latouche, R. Lattanzi, A. Laurent, A.
Lauterbach, E.H.
Le Gall, T. Le Gallic, Y. Le Hyaric, M. Le Roux, C. Leanna, M.R.
005, 141 172 373 381 253, 255, 271 323 155 165 304 250 313 295 099, 146 330 106&190 115 184, 203 114 145 295 205 134, 186, 222, 225, 238 027, 076, 078, 122, 188, 207, 279, 301, 319, 323, 336, 351, 367 216 150 208 049, 165 285 305, 350 088, 223 197 112 312 203, 277,282 328 026, 133 158 222, 280 285 006 172, 357 357
Author Index
Lebeau, E. Leblanc, C. Leblmc. Y. LeBoulluec, K.L. Lebrun, A. Leclerc, R. Leconte, M. Lecouvery, M. Lectka, T. Lee, B. Lee, B.Y. Lee, C. Lee, C.-S. Lee, D-H.
Lee, G.H. Lee, H.J. Lee, H.K. Lee, H.W. Lee. I.-Y.C. Lee, IS. Lee, J. ee. J.C. Lee, J.H. Lee, J.M. Lee, J.R. Lee, J.W. Lee, K. Lee, L. Lee, L.Y. Lee, N.E. Lee, N.H. Lee, S.B. e. S.G, Lee, S.J. Lee, S.W. Lee, V.J. Lee, WK. Lee, Y. Lee, Y.R. Lee, K.C. Lefebvre, F. r. BCB,
128 026, 294 131 120 246 113 356 217 297 073 364 180, 204 276 028, 182, 337, 028, 354 181 101, 271 271 334 276 053, 271 351 032 017, 359 321 192 126 136, 161 046 289, 105 163 105, 371 162 136 356 127
341
325
106, 180, 308, 325, 354 182, 226,
226
101, 158
146
162
364
121
Author Index
415
LeGall, T. Lehance, P. Lehuede, S. Leijonmarck, H. Leiva, G.C. . J~fM.am. N Lemaire-Audoire, S. LeMenez, P. Lemeune, S. Lemini, C. Lennick, K. Lenoir, J .Y. Lentz, R. Leonel, E. Leong,W. Lerman, 0. Leung, C.W. Ii, Leurs, S. Levart, M. Levett, P.
036 049 073 191 134 073, 129, 278 137 050 209 033 078 093, 122 173 037 028 319 165, 202
Levina, A. v. S.V‘ Lhoste, P. Li, C. Li, Li, G. Li, J. Li, KS. Li, N.-S. Li, P. Li, S. Li, T. Li, W-R. Li, X. Li. Li, 2. Liang, L. Liao, H.-Y. Liao, L.-F. Liao, Q. Liao. Liao, Y. . ebesu Likhomanova, Lillie, B .M.
151
T.I.
104, 158 138
311
165
160 233 023,037 087 139, 172 180, 308 077 324, 342 128 204 137 143 136,204, 226 381 140 142 375 191,204 180 300 222, 366, 368 356 206
Lim, Lim, Lin, Lin, Lin. Lin, Lin, Lin, Lin,
J-S. S. C-C. C.-H. N.-S. R. R.Y. 2.
Lindsley, C. Ling, R. Linquist, A. umelle. Cr. Lintanf, V.
Liu, G.-B. Liu, H. Liu. Liu, K. Liu, P. Liu, S. Liu, Y. Livingston,
R.C.
Llavona, L. Llebaria, A. Llera, J-M. Lo, KM. Lo, M.M.-C. Locati, L. Lofstom, C. Loh, T.-P. Lohray, B .B. Longeray, R. Longmire, J .M. L6pez, C.J. Lopez-Leonardo, C. Loreto, M.A. Lough, A.J. Louie, J. Louis, D. v. G ove. BE
276 038, 214 245 149 156, 373 030 206,364,369 155 386 144, 177 215 327 378 240 128 253,255,271 042, 087, 088, 215, 240 053 107 251 210 090, 249 080,082 069 287 241 342 320, 354 208 275 275 093, 186 094 285 218 145 373, 390 245 375 133 203 130 335 005, 007, 115, 141 118, 131
416
L-M
Lovely, C.J. Lu, L. Lu, s. Lu, S.-P. Lu. I= L Lu, Y.-Q. Luan, L. Ludwig, R. Luh, B.Y. Lunch, M.-J. Lund, T. Lundberg, S. uo. F.-T, Luo, X.-L. . Luteyn, J.M. Ltitjens, H.
M’Bida, A. Ma, S. Maas, P.J. Mabuchi, T. Macchia, F. dOnald.
MacKay, M.F. Madhavan, S. Maeda, H. Maej ima, K. Maekawa, H. Maeta, H. Magarita, R. Maggi, R. Magnanti,
S.
Mahadevan, A. Mahdavi, F.
231 133 156 355 056 328, 340, 037 058 185 148 071 327 175 146 239, 073 272, 129 278 196, 299,
335, 337, 353, 369
Author Index
Mahler, R. Mahmood, IS. Mahmoud, K. Mahuet, E. Maier, S. Maikap, G.C. Maillard, B. Maiti, PK.
154 200 169 130 242 101, 362 336 013 050 181
Maity, G. Majee, A.
360, 371 382
255 331
352 043, 206, 282, 335 288 299 254,256,271 192 197 011,051 033 048, 177 235 030,090, 194, 332 284, 376 349 109, 140 058, 062, 254, 330 343 235 390 136
Majidi, A. Majo, V.J. Majoub, M. Mak, C.-K. Makata, T. Maki, T. Makihira, I. Makioka, Y. Makuta, T.
Malawska, B. Mallaiah, K. Man, T.-O. Manage, A.
Mandal, P.K. anhas. MLS, Manju, K. Manoury, E. Mansilla, H. Mansuri, M.M. Mansuy, D. Manuel, G. 0. c, Marcantoni, E. Marcelo-Cur-to,
M.J.
037 028, 076, 080, 082, 350 286 115 141 197 226 370 048, 177 072 003, 134, 201, 248, 362 257 082, 215 134, 186, 222, 225 289 265 226 338 178, 239, 261, 338, 368 057 101,299 350 163 166 071 220 178 123 038, 090, 223, 371, 382,386 145 111,186
Author Index
Marcoux, J.-F. ek. L
Marinelli, F. 6. LE, Marmon, R.J. Marolewski, A.E. Marotta, E. Marquais, S. Marques, C.A. Marquez, V.E. Marrs, C.M.
Martel, J.P.
Martin, Martin, Martin, n. Martin,
G. M.W. P.S. S.E S.E.
Martinez, J.A. Martinez, J .P. Martinez, L.A. Martinez, M.A. Martorell, G. Maruo, M. Maruoka, K. Maruyama, T. Marvin, M. Maryanoff, C.A.
Masaya, K. Mascaretti, O.A. Masdeu, A.M. Mashimo, T. Masquelin, T. Massanet, G.M. Mastropietro, G.
M
099 066, 081, 215, 241 312, 313, 314, 317 351 037, 262, 336 126 258 152 066,222 152 012 299 022, 154, 169 103, 105, 263 036, 222, 280 015,018 016 220 252 312 300 231 081 289 369 277 048 068, 355 017 074 347 019, 052, 092, 159, 194,200 257, 269, 279 191 112 047, 160, 342, 388 020 010 114 073 058 329 335
417
Mastrorilli, P. Masuda, H. Masumi, A. Masumoto, K.
Mata, E.G.
Mathew, L. Mathews, A. Mathur, R.K. Matikainen, J.K. Matos, C.R. Matsubara, Y. Matsuda, H.
Mats&, T. Mats&a, G.R. Matsuhashi, H. Matsui, T. Matsukawa, S. . ukr. K. umoto. I(, to. Matsumoto, Matsumoto, Matsumoto, Matsumoto,
M, 0. S. T. Y.
Matsuo, G. Matsuo, T. Matsuoka, S. Matsushita, H. Matsushita, K.
Matthews, D.P. Mattii, D. Matusnaga, S. Maughon, B .R. Maumy, M. Mauriello, G.
167 144,266 262 324 025, 117, 348, 363, 372 010 053 063 056 286 169 055 219 357 223, 273, 307 030 095, 193, 237, 370 372 355 010 070, 187,378 041, 273,282 260, 279 140 123, 187, 291, 303 075 326 379 178, 196 220, 271, 379 296 354 183, 248 239 035,049,079 338 041, 282 201 080 353 042 063 303 343
418
Mavropoulos, I. Maw, G.N. Mawson, S.D. Mayadunne, R.T.A. Maye, J.P. 5.4, Mazal, C. Mazzanti, G. Mazzone, L. Mbiya, K. c-v. J.Ic, McCloskey, P.J. McCord, D.J. McCormick, G.J. McCreadie, J.G. McDonough,
C.S. , McGuigan, P. McHardey, S .F. McIntosh, J. McKennon, M.J. McKerlie, L.A. ev. U McKie, J .A. McMillen, H.A.
Meanwell, N.A. Mebane, R.C. Mecichetti, S. Meguro, M. Mehler, T. Mehrotra, B. J.K Menezes, P.H. Merkert, J. Merriman, G.D. Merzouk, A. e&ger. J.0, Meulemans, T.M. Meyer, A.G.
M
158 218 326 294 121 168, 349 340 377 162 084, 377 114 080 180 063 165 003 143,206 264 209 109 286 102 124 011 366 286 037,160, 193 074 357, 358 243 294 327 167 189 253,257,289 015,016 383 129 238 263 312 041, 132, 279 129 138 154, 344 341 109
Author Index
Meyer, C. Meyer, F.E. eu Mezzina, E. Michael, F.E. Michael, J.P. Michos, D. Middlemiss, D. Migita, T. Mihara, S. . . 1kaml.K Mikami, S. Miki, M. Mikdajczyk, M . Milenkov, B . Militor, E. Miller, D.J.
Miller, S .J. Milligan, G.L. Mimero, P. Mimura, N. Min, S.J. Min-Min, G. Minami, Y. Minato, M. Mincione, E. Mingardi, A. Minidis, A.B .E. Minoshima, T. . Wskl.
Miranda, E.I. o Morew. Misco, P.F. Mitamura, S.
Mitra, A. Mitsudo, T.-u.
M.J&
066,081,241 339, 378 011, 041,066, 075, 119, 210, 292, 370,373 309 117 065,347 073 363 240 161 015, 260, 279, 317,379 165 220 233 334 113 326 216 115 224,297 112 328 277 183 221 149 135 272, 382 340 150 177 036, 221, 222, 234,280,381 052, 141 205 027 071 197 341, 371,380 181 361 045 131 339
Author Index
281 091,214, 348 196 Miura, T. 047,342 Miwa, K. 003,053 252 Miyagi, W. Miyai, T. 237 021 149 Miyamoto, M. 141, 146, 155 Miyashita, M. 166,207 Mivata. Miyata, 0. 311 274 Miyata,M. 078, 195, 281, 352 Miyoshi, N. 024, 268, 269, 372 Miyoshi, S. 155 141 Miyoshi, So. 069 Miyoshi, T. Mizuho, Y. 376 Mizuno, M. 376 Mizuno, T. 030 242 nova & MO, X.-S. 236, 282 Mochizuki, H. 215 Modi, D.P. 112, 373 056 166 Mohammadpoor-BaItork, I. 007 0m 170 Mohand, S.A. 049 Moher, E.D. 351 Mohr, B. 361 ohr. P, 352 Mohri, IS. 386 248,280 MQ%L 037, 160, 193, 261, 346 . olina. P, 305, 375 Mollenaar, M.H. 291 Momeni, A.R. 170 ose. T, 006 Monkovic, I. 120 Montana, J.G. 010 Montanaari, V. 229 Montaufier, M-T. 165 Miura, I. Miura, K.
419
0. G,
.
onteveca PC, Montgomery, D. Montserrat, J.M. dv. CJ, Moody, H.M. oare. J& Moore, W.J. Moor-lag, H. Moran, M. Mordini, A. Morera, E. Moret6, J.M. Moretti, N. Mori, A. Mori, H. Mori, Mori. Mori, T. Mori, Y. Morii, N. Morii, T. Morikawa, K. Morimoto, T. Morishima, Y. Morita, K. Morita, Y. Moriuchi, T. Moriwaki, M. Moriyoshi, N. Morken, J.P. Moro, S. oro-Oka. Y, Morodome, M. Morris.. omson, H, Morrison, J.J. . rer. J, or-ton. m 0rtreux.A. Mosleh, A. oset. P,
333 135, 353 096 067 326 244 175 196 309 198, 370 077 335 320,354 058 299 274, 378 159 001, 075, 089, 100,278,321 273, 325 232, 252 095 102 100 216 247 095, 143,230 036 324 272 165 197 036 247,279,322 174 019 127 114 240 062, 070, 244, 306 357 129 068 128
420
M-N
Mossman, C.J. Mothaghineghad, E. 0QerwelL W& Motofusa, S. Motohashi, S. Mottadelli, S. Mould, R.J. Mouloud, H.A.H. Mouri, M. Mouries, V. Moutou, J.-L. Moyroud, J. uchowskr, . J.M Muci, A.R. Mueller, P.H. .T, Muhammad,
F.
Mukherjee, S.B. Mukhopadhyay, M .. Muldowney, M.P Muller, C. Mtiller, M. Mtiller, T.J.J. Muiioz, S. Muraglia, E.
Murai. Murai. Murai. Murakami, C. . urm plrl, Murakami, Y. Muraki, T.
112 157 098, 328 089 383 179 321 250 163 269, 279 378 008, 112, 313, 334 062,070, 244 061, 146 032,040 059, 238 361, 362 133 034, 141, 146, 155, 163, 164, 165, 166, 167, 169, 185, 231, 325, 390 338 101, 362 113 130 270 147, 275, 309 379 143 305, 327 151,196, 293 110, 153, 155, 166, 186, 188, 237, 267, 268, 376 302 071, 074, 084, 095, 216, 250, 374 092 035 001,045,253 267 142
Author Index
Muramatsu, Y. Murase, N. Murashima, T. Murphy, C.K. UU
Murry, J.A. Mutch, A.
344 052, 232, 278, 130 102 356 047, 151,
194 387 386
049, 130, 187, 188
Mynett, D.M. . ir. U.& Nadkami, D.V. Nagafuji, A. Nagahara, K. Nagaku, M. Nagaraju, S. a. T, Nagashima, H.
Nagayama, S. Nagino, C. Nagoyoshi, M. Nair, K.B. Naito, M. Naito. NBiera. Nakagawa, T. Nakaharu, T. Nakahashi, M. Nakai. Nakajima, M. Nakajima, N. Nakama, T. Nakamura, D. Nakamura, H. Nakamura, I. Ill-&K&
Nakamura, T. Nakanishi, Y. Nakano, S. Nakao, H. Nakata, M. Nakatani, S.
108 214 201 333 060 143 290 292 034, 163,164, 165,231 308 060 348 329 220 254,3 11 315 023,024 108 248, 362 282 147 126 282 055 067 025, 187,253 237 012,031,033 013, 267 035 006 354 054
Author Index
Nakayama, K. Nakayama, M. Namkoong, E.-Y. Namli, H. Nanda, B. Nanni, D. Nantermet, P.G. Naota, T.
Narayana, C. Narizuka, S. Narla, G. o. F.
Nativi. Natsume, H. Navio, J.L.G. Nawa, S. Nayak, A. Nayyar, N.K. Nazareno, M.A. N&Hec, J.-Y.
Negoro, N. Neh, H. Neibecker, D. Neil, D.A. Neiteler, C. Nei teler, G. Nelson, L.T.J. Nelson, S .G. Nelson, J.A. Nemoto, H. Neri, S. Neset, S.M. Nestor, N.B.
421
166, 197 282 282 045 054,083 070 070 246, 269 023 128, 135 366 213 151, 153, 166, 186, 188, 196, 267, 268, 293, 376 114, 115, 198, 314, 361 011,051 012 292 249 084, 233, 234, 300, 377 263 379 242 069 023 104 079 067,068,093 077, 083, 121, 302, 340 047 089, 091, 092, 093 008, 132 353 194 194 311 032 216 253, 334 167 103 143 227, 302
Neyer, G. Nguyen, S .T. Nicaise, O.J.C. Nice, L.E. Nicholson, L.W. Nickisch, K.
Nie, X. Nielsen, J.K. . . iem1. M, Nikat, S .M. . . . ikrsb. GL Nilsson, Y.I.M. Ninomiya, I. Nishibayashi, Y. Nishida, M. Nishida, S. Nishide, K. Nishigaichi, Y.
Nishikawa, A. . . ishrI&o. T, Nishimata, T. Nishimura, K. Nishimura, M. Nishino, H. Nishio, K. Nishio, M.
Nishiyama, Y.
Nishizawa, H. . . rshlzawa. Niu, Q.J. Njardarson, J.T. . obrle. CE
248 137 161 223 126 143, 206 320 255 089, 091, 092, 093 109 305 032 033 302 135 346 360 254, 311 032 085 019,021,290 055 277 030,061, 148, 332 108 329 075 110 108 385 018, 022, 095, 267, 277,280 193,266,370 012 060, 176, 177, 311 144, 152, 166, 189, 197, 255, 266, 324, 347, 362, 367 246 159 195 384 167
422
Noda, K. Noda, Y. Node.. Noe, M.C. Noheda, P. Nomura, M. Nomura, N. Nomura, R. Nongkunsam, P. orm,,ant. J.-F, Norris, D. J. orb. M Norton, J.R. Norwood, B .K. Nosal, R. Nowotng, S. Novori. Nozaki, K. Nshimyumu Kiza, P. t. WA& Nuhrich, A. Nukui, S. Nunes, M.L.P.G. Nwaukwa, S. Nymann, K.
O’Rourke, D. Oba, M. Obora, Y. recht. Occhiato, E.G. Ochiai, K. OcW. M. Ochiai, 0. Oda, H. da. M, Oda, T. oda, Y. Odagaki, Y. odaka, H. Odens, H.H. Oehme, Gy
N-O
231 077 055 248 190, 287 196 377 237, 254 108 066, 081, 215, 241 258 275 292 384 062 016 033,036,245 054,055, 362 114 225 250 297 167 019 114 266 139 060, 17, 177 216 058 383 344 388 148 240 148, 149, 220 092 151, 166, 188, 196 370 380 122 287 132
Author Index
Ogasawara K. a& Ogawa, H. Ogawa, S. Ogoshi, S. Oh-e, T. Ohashi, M. Ohe, K. Ohga, Y. Ohhara, T. Ohira, M. Ohkuma, M. Ohkuma, T. . on. n Ohno, A. Ohno, Ohno, 0. Ohrai,
H. R. T, K.
Ohta, T. Ohtake, Y. Oi, S. Qjioma. L Okamoto, S. Okamoto, T. Okamura, A. Okamura, K. Okauda, M. Okita, H. Okita, T. ku. A, Okuda, F. Okumoto, H. Okumura, T. Okuro, K.
276 051, 052, 286 376 153 095 260,291 386 225 078 326 095, 302 267, 268, 372 262 049 325 033,036 048,079, 012, 031, 086,259 274 305 061, 148 272 063, 165, 337 260 262 061 201 338 290 024, 194, 246, 351 022 179 089 252 296 238 235 311 177, 297, 369 196
284,
269,
177 033,
172,
214,
307
Author Index
O-P
Olano, B. Olive, J.L. Oliveira, E.R. Olivero, S. Olmstead, T.A. l&n. R.& Olson, S.H. Omata, K. Onishi, H. Ono, K. Ono, N. Onouchi, J. Ooi, T. Ooka, H. . Ordofiez, M. Orelli, L.R. Orito, vama. T, Orliac, A. Osada, A. Osbom, H.M.I. . shlu
Oshima, T. Oslob, J .D. Osterhout, M.H, Ostwald, R. Otani, S ter; Otten, P.A. Oumoch, S. Oussaid, A.
Oyasato, N. Ozaki, F. Ozaki, M. Ozaki, N. Ozanne, N.
143, 161, 191, 204,232,356 318 096 085 029, 160 368 117 275 241 305 092 080,291 214 135 052, 194 033,036 225, 300 050 088, 223 174 029, 148, 149, 355 390 335 235 109 187, 190, 214, 251, 274, 359, 388 258 150 253 278 303 022, 150 390 252 172 012,213 317 376 061 292 079 219
219
423
077 Pacifico, S. Padmakumar, R. wa. A, Pagano, S. P.C& . 1. It& Pai, C.-C.
s. F, Palani, A. Palani, N.
Pallan, P.S. Palucki, M. Pamment, M.G. Pan, S.-F. Pan, Y. Panchenault, D.
Pandley, B . an& J.S. Paneque, M. Pankayatselvan, R. . 10. puz
Paolobelli, A.B. tte. L.A. Para, KS. SL Pareschi, P. Paris, J.-M. Park, B.K. Park, C.-H. Park, C.M. Park, D.-C. Park, H.S. Park, J.
234 338 059,366 356 229,230 113, 229, 230, 328, 343 055 028, 182, 226, 354 131 317 253, 264 052 003, 180 381, 387 172 256, 371 165 151 086, 137 109 146 044,205 091, 179, 193, 199, 304 056 157, 258 099 172 309 285 263, 346 368 178 128 137 229 024, 083,281 325 024, 187, 281, 283 334 247
424
Author Index
Park, J.H. Park, K. Park, K.H. Park, Y.C. Park, Y.J. Parks, D.J. Parquette, J.R. Parrain, J.-L.
Pastor, A. Pastorio, A.
Patel, R. Patiiio, R. Patra, PK. Patro, B.
Patzel, M. Paul, V. Payne, A.N.
Pedregd, B. Pedrini, P.
Pellacani, L. Pellegrino, R. Pelletier, J.D. Pelton, E.A. Peiia-Cabrera, E. Peng, G. Peng, Z.-Q. Pepito, ccc. Pereira, Pereira, Pereira,
AS V, C. M.M. S.
351 046 325, 337 386 343 367 069, 245, 264, 365 290 088 231 305 058 307 137, 149 056 048 056 198 198 200,212 249 300 174,270 043 117, 124, 320 294 357 242, 306 189 143 017 133 229 171 373 258 222 134 339 179 278 069 145 167 355
Pereira-Martins, E. Pereyre, M. Perez de Heredia, I. Perez, M. Perez-Encabo, A. Perez-Flores, J. . em. w Perichon, J.
Pennumal.* P&ot, G. Persson, E.S .M.
Petit, A. Petre, D.
Petrov, V.A. Pe yrat, J .-F.
Pfister, K.B. Pfister, X. Philippot, K. Philips, E.D. Phillips, O.A. Piazza, M.G. Piers. Pietruszka, J. Pigeon, P. Pillai, S. Pillai, S.K. Pinel, C. Pineschi, M. . 1. A, Piombi, B. Pique, C. Piqueur, J. Pirrung, F.O.H.
184 336 317 185 017 050 011, 122, 127, 203 036, 038, 067, 068, 093, 152, 184, 239 158,310 283 145 115 219, 355 141 220 038, 382, 229 014 099, 125 352 033 132 388 050 349 015 332, 163, 233, 266 007 104 243
223, 315,
202, 371, 386 150
349 375 164 234
254, 256,271 229, 343 152 099 124 329
Author Index
Piva Pizzo, F. Planchenault., D. event, J.-C, Platzer, N. Plobeck, N.A. Podlech, J. Poel, T.-J. Pohmakotr, M. Poiana, M. . omdexter. G& . . elm. D, Poirier, J.-M. Poli, S. Polizzi, C. Polleux, P. Pollini, G.P. Pollock, C.M. t. J-C, Ponzini, F. Poon, C.-D. Pore, V.S.
Porto, C. Post, A.J. * Pouilhes, A. Poveda, M.L. Powell, L.W. Prajapati, D.
% Prasad, A.D. Prasad, KG. Prechtl, F. Pregnolato, M. Prince, A.A.M. Prins, T.J. Ptock, A.
P-Q-R
162 180 147 229 099 303 241 098 296 258 358 123 120 171 344 189 238 147 250 111 306 111 226 356 256,270 094 058 114 007 114 099 384 137, 218, 304, 318 045 232, 143, 191, 204, 356 102, 350 217 138 011,051 270 229 115 028 119
425
Punniyamurthy,
T.
Punzi, A. Purick, R.M. Pushpavanam, P. Pyun, C.
Qabar, M.N. Qi, H. Qi, L. QkuL Qian, C.-Y. Qing, F.-L. . xh. GL le. P, Quesnelle, CA. Quiclet-Sire, B.
Racha, S. Rachdi, F. Racherla, U.S. Rachita, M.J. Radinov, R. Radzilowski, E.M. Rahimizadeh, M. Rahman, S. Rai, R. Raimondi, L. Raina, S. Rairama, R. Rajagopal, D. RajanBabu, T.V. Raje, P.S. Rajesh, C.S. Raju, S.V.N. Raju, V.S. Ram, B.
Rama-Devi, T.
165, 187, 188, 190, 191,360 111, 186,300 288 101 146
078 252 331 329 385 174 031,249 053, 085, 143, 339 068 105 333 264, 365 065.220 381 168 235 216 094 195 059 143 067,082 111 047, 359 021 066 054 118 168 278 299 034 010,055 075 374
426
Ramaiah, P. Ramaseshan, M. Rambaud, D. Ramdani, M. Ramesha, A.R. Ramig. Ramkumar, D. . Ram&r, D.J. n. CA Ramser, M.N. Ranaivosata, J.-L . Rane, A.M. Raner, K.D. Ranjbar, Y.
Rao, B.R. Rao, G.V. o. HS.P, 0. I,M. Rao, KS .S.P. Rao, M.L.N. Rao, R. Rao, T.B. onort. q,& Rasmussen, KG. Rath, N.P. Rathmell, R.E. Rathore, R. Ratovelomanana, V. Ratovelomanana-Vidal, Raubo, P. Raut, S.V. Ravenscroft, P. Ravi, D. Ravikumar, KS.
Ray, J.E. , Rechsteiner, B. Reckziegel, A. Reddy, Ch.K. Reddy, G.S .R.
Author Index
232 109, 140 293 007, 141 107, 324 330 229 141 250 108 300 053 052, 245 102 170 037, 039, 045, 085, 269, 330 034 303 135 193 179 203 173 193 138 168, 309 381 321 386 067,239, V. 033 262 239 020 141 013 193, 169, 201,205 007,267, 138 184 312
238 011, 127 141
Reddy, J.P. Reddy, K.L. Reddy, M.M. Reddy, M.V.R. Reddy, N.K. Reddy, N.P. Reddy, P.N. Reddy, R.R. Reddy, R.S. Reding, M.T. Redman, A.M. Redpath, J. Redy, M.V.R. 041, 086,
311
eves. W.P, Refvik, M.D. Reginato, G. Reiche, P. Reihs, S. Reilly, M. Reinhard, E.J. Reinhold, T.L. Reisse, J. ReifjiL H -U Reitz, D.B. Ren, J. Ren, P.-D. Rennels, R.A. Renyer, M.L. Repic, 0. Resci, S. Resek, J.E. . esm. G, Resta, S. Restituyo, J.A. Reum, M.E.
172, 365 Reynolds, K. Reynolds, K.A. Rezanka, D.S. Rhee, Y.H. Rho, H.-S. Riazi-Kermani, F.
253 075 075, 101, 295, 296, 336,362 203, 383 012 114 154,261 044,056 026 280 203 387 009, 199, 251, 257, 328 173 317 198, 370 252 166 225 114 366 023 260 114 131 086, 137 019, 130 030 138 088 373 229 081, 107, 169 110 197 124 358 168 096 376 258 337 187, 283 237
Author Index
Ricci, A. Rice.
Richardson,P.F. Richter,M.J. Richter,N. Rieger. Riesinger,S.W. Righi, P. Risch. Rispens,M.T. Rist, 0. Riva, R. Rivera, A.D. Rivera-Fortin,M.A. Rivero, LA. Robbi,E.W. a Roberts,L.R. Roberts,S.M. Roberts,W.M. Robin, S. Robinson,R.A. Rodriguez,B. . odnw J.pLB, Rogers,C. Rogers-Evans, M. Rolfing, K. * Rollin, Y. Romagnoli,R. Romani,M. omero.D.J,, Ronne,E. Roof, M.B. Roof, M.T.S. Roos,E.C. Rosa,A. Rosado,I. Rosauer,KG. Roschangar, F. Roshchin, A.I.
427
R-S
162, 198 061 311
265 346 161 039, 067, 093, 195,339 366 078, 113 027, 267 152 131 151 175 316
046 345 171 299 082 098 349
Rossi,L. Rossi,L.I. . Sl.
It&,
Roth, G.P. Rousselet, G. Rousset,C.J. Routledge,A. Rovis, T. ov. SC, Royer, AC. Rozema,M. Rozema,M.J. Rubiales,G. Rubina,K. Rubinstein,H. Rubio, A. Rudorf,W.-D. Russell,A.T.
041 154
043 191 134 332 105 251 038 239 291 125,228 121 120 042 158 116,291 268 052 272 296 069
Ryan, J.H. u. E.K. u. I,
Sadakane, M. Sadayori,N. SheMelo, M.L. Saeki,N. Sagar,A.D. Saha,AK. Saha,M. SaiU, M.K.E. Saieo.
152 loo, 109, 110
Saikia,A.K.
252 027,294 231 079 042,222 239, 327,344 303 214 327 282 044,057 327 014 278 173 385 317 349 257 242 384 094 299 090 285 197 062, 116,132 052, 143,284, 286, 333 074 166 080 297 253 027 298 265 186 285 039, 041, 045, 086 373 020, 062, 128,
323 390
428
Saini, N. Saito, T. Saitou, K. Sakaguchi, S.
Sakai. Sakai. Sakai, N. Sakai, T. Sakakibara, Y. sakamoto, K. oto. T, Sakata, Y. Sakurai, M. Saleh, S. Salehi, P. Salemkour, M. Salomon, C.J. Salou-Guiziou, V. Salunkhe, A.M.
Salunkhe&& saluzzo, c. Salvador, J.A.R. Sambri, L. Sanabria, R. Sanchez, M.E.L.
Sanetti, A. Sano, T. Santagostino, M. Santhi, P.L. Santiago, B . Saoudi, A. Sarangi, C. Sarawathy, V.G. Sardarian, A.R. Sarko, C.R. Sam-m, K.D. Sarma, J.C.
Author Index
350 019, 338, 368 267 086 144, 189, 197, 347, 362 189, 356 215, 281,376 054, 055 032,265, 363, 372 215, 376 097 030, 065, 282, 324 347 156 045 263 285 010 120 136 186 328 027 090, 223, 382 205 349 175 137, 218, 304, 318 272, 382 056,093, 229 355 049 043, 044, 057, 217 210 119 023 093 101 034,041,085 035 181 363
.
orl. G, Sasai, H. Sasaki, A. Sasaki, H. Sasaki,H. Sasao, S. Sashima, M. Sasidharan, M. n. Y, Satish. o. F, Sato, Sato, Sato, Sato,
H. K. N. T.
Satoh, H. h. T, Sattigeri, J.A. Satyanarayana, J. Sauvetre, R. Savignac, M. Savin, K.A. Sawada, T. Sawick, D. Scaarpi, D. . cem. A, Schedler, D.J.A. Scheloske, M. Schiano, A.-M. . chrck. H, Schick, U. Schlingloff, G.
Schmitt, M. Schmitz, C. Schneider, M.F. Schoemaker, H.E. Schonk, R.M.
058, 062, 254, 330 270, 382, 384 345 164, 169 215, 376 164 293 115 149, 169 332 205 023, 024, 098, 214, 246, 351 089, 114 005 362 084, 108, 150, 330 075, 091,241 351 177 160, 196, 236, 383 046, 181, 182 265 244 129, 137, 138, 378 226 053 056 383 186,355 119 010 123 148 378 151, 153 387 085 313 378 374 291, 329 389
Author Index
Schreier, J.A. Schroder, F.
Schultz, A.G. Schulz, D.J. Schumacher, R. SchUer, M. chwa & Schwarm, M. cha Schwarz, R. Schweizer, W.B. Schwenkreis, T. Schwink, L. Scolamiero, C. Scopes, D.I.C. cott. A& Scott, M.E. cott. W.J, Scotton, M. . crewr. A, Secundo, F. Sedergran, T.C.
Sega, A Segawa, K. Seger, A. Sehata, M. Sehgal, A. Sehon, C.A. Seitz, W.J. Sekhar, B .B V.S. Seki, IS. Sekine, S. Sekiva. Sell, M.S.
Selva, M. Selvapalam, N.
429
272 225 118 318 364 212 273 340 050 273 317 011 035,069 094 032 162 040 093 318 174 235 066 313 088, 093, 223, 343 229 238 032, 296 338 313 032 031 369 249 169 188 097 179 292 071 175 039, 339 195 311 152 260 352
Semones, M.A. Seneviratne, V. Seo, W.W. Serdyuk, L. Sereda, G.A. Serra, AC. Seth, P.P. Seth, S.
Shang, X. Shanklin, M.S. Shankweiler, J.M. Shannon, I.J. Sharifi, A. Sharma, P.K.
Shaw, A.W. Shen, C.-X. Shen, C.-Y. hen. Y, Sheng Jian, L. Sher, R. Sheu, J. Sheu, L.-J. Shi, B.Z. Shi, D. Shi, J. Shi, L.-P. Shiao, M.-J. Shibagaki, M. Shibakami, M. Shib& M,
Shibw Shibata, N. Shichijo, Y. Shida, N. S hieh. W.-C,
059, 366 228 079 014 373 356 167 315 003, 239 347 268 365 251 054 104 239 056 350 012, 191 023, 363, 040, 217, 246, 247, 251, 252, 143 174 365 338 016 101 123 056 090 184 363 098 155 035,049 175 258, 270, 278, 297, 384 095, 193, 237, 370 291, 342 153 315 033
390 245, 250, 311
272, 382, 202,
430
Shigeizumi, Shigyo, H. Shiigi, J. Shiina
Author Index
S.
SInimada, I. Slhimada,S. sl Slhimamoto,M. Slhimano,M. sl himizu. SIhimizu, IS. SIhimizu, M. sl E. Slhimotsuma, Slhimoyama, I. Slhin, D.-S. Slnin, H.H. Slhinada, T. S1hindo, M. Slhindo, T. S1linokubo, H. sl hioiri. Slhiraishi, Y. SIbiro, M. Slnirouchi, M. Slniue, J-S. Slnivaramayya, K. Slnoda, H. SIhon, Y.S. 2i.l Shook, C. Short, KM. Shymanska, M. . . ibi. NI& Sibille, S. Siddiqui, M.F. Siedlecka, R. Siegel, M.G. Sienkiewicz, K. Sierra, M.A. Siesel, D. Sigman, M.S. Silveira, C.C. . ilveu Sim, H-S.
356 061 277 141, 146, 155, 325 092 323 226 017 041,370 257 378 304 061 152 340 036,222,280 386 287, 330 076 134 190, 359 003,053&335 316 201,256, 330 159, 251 245 308 267 013, 135 036, 090, 194, 254, 299 354 385 349 093, 191, 192 067,068 217 230 313 307 144 082 317 238 275 276
Sim, T.B. Simonot, B. Simonti, M.C. Simova, S.
Singer, M. Singer, R. Singer, R.A. Singh, A.P. Singh, G.P. Singh, J.D. Singh, L. Singh, R.P. . rnrrh. V& Singh, W.P. eton. D.k Sinisterra, J.V. Sinou. Siva, P.
Slattery, B .J. Sliwa. Smallridge. A.L Smeets, W.J.J. Smith III, W.J. Smith, D.B. Smith, DC. Smith, D.T. Smith, F.C. Smith, L.A.
nvder. DC, Soai. Sobti, A. Sochanchingwung, Sodeoka, M. Soderberg, B.C.
R.
086, 110 390 327 263 037 124, 383 025, 035, 119, 125, 136, 192, 201, 255 176 195 018 056 165 032 010,055 086 047, 359 230 065, 277,280 241 160 160 135 135 021,038 230 167 227 353 258 019 176 299 105 236 239 110 106, 123,289 181 372 068, 105, 276, 386 171 017 341 193 258, 272,297 122
Author Index
431
Soej ima, T. Sol& D. avm. A, Soloshonok, V.A. 4 Somasunderam, A. Sommovigo, Son, H.S. Song, H. Song, J.-S. Sonoda, M. onoda. N,
M.
Sorensen, C.M. Sosonuk, SE. Souma, Y. Soundararajan, N. Soundararajan, R. Spagnol, M.D. Spagnolo, P. Spalluto, G. Sparacino, M.L. ecm. W.n Spek, A.L. Spetseris, N. . . hilling C .D, Spinetti, L.M. Sprules, T. J. . mk. M, Sridhar, M. slidharan, v.
Srivastava, R.S. Srivastava, S .K. Staangeland, E.L. Stabler, S .R. Stachel, S.J. Stadmiiller, H.
052, 141, 224, 245 090 320 118 243 329 171 009 320 084 118 190 058 071 051, 052, 143, 284,286, 333 146 356 029 238 184 135, 353 250 146 116, 291, 019 292 381 383 192 023, 133, 355, 358 202 202, 203, 213, 283 046, 143, 181, 182, 369 174,270 008, 320 302 035 146 071 078
329
190,
rd. J.A. Stallman, J.B. J.-F, Stammler, R. Stanczak, A. Stanoeva, E. Star$ I.G. St&, 1, Staszewski, J.P. Stavber, S.
Stefani, H .A. S tembach. JCE, Stenig, A.G. S tenkula, M. Stephenson, P.T. Stetson, K.A. Stevens, C.V. Stevens, E.P. Stevenson, R.J. Stewart, SK S tingl, IS. Stojanova, D.S. stout, C.W.
Strazzolini, P. Street, L.J. . kowskl. Strickland, J.B. Stiidemann, T. S tudley, J .R.
212, 160, 265,
S turino, C.F. S turmer, R. Su, Q. su.. Suarez, A.R. ubba Rao. G.S.R. Subramanian, L.R. Sucheta, K.
116 389 291 215 171 310, 347 142 142 219 342 167 121 238 095 339 337 125 366 122, 125, 172 124 096 295 360 301, 318 018 334 313 348 102 123 344 312 280 070,078 031 136 130 040 363 230 231 217, 292 060,187 068,081,355 141 115
432
Sudoh, T. Suehiro, I. sugamoto, K. Sugawara, T. sugi. Sugihara, S. Sugihara, T. Sugihara, Y. Sugimoto, K. Sugimoto, T. Sugino, A. Suginome, M. Sugiura, M. Sugiyama, T. Suh, D.-J.
Sumiya, T. Sun, L. Sundermann, M.J. Suresh, S. Suriano, J.A. Suslova, E.N.
Suzuki, M. Suzuki, N.
Suzuki, T. Svendsen, J.S. Swafford, A.M. Swapna, V.
Sznaidman, M.L. .
zvmon&J
S-T
149, 169, 172, 174, 193, 270 341 345 041,282 176 150 290 302, 340 276 356 152 379 127, 174,277 042, 376 214 289 266 341 055 342 376 149 367 157 088 078, 352 013, 387 164, 196, 376 075 078, 215, 380 382 257, 327 057 109 047
Author Index
Tabaei, S .H.
Tae, J.S. mliavini.
E,
Tahara, Y. Tajiri, K. Takacs, B .E. Takada, K. Takada, T. Takahashi, E. Takahashi, H. Takahashi, K. . 1. M, . 1. s, .
1.T, Takai. Takai, T. Takai, Y. .
1. I(,
195, 281, 063, 232,
Takano, M. 0. s, Takanobe, K. Takase, K.
169, 185, 251, 284,
212, 214, 377, 379,
266
209 248,280
Takayanagi, H. Takazawa, N. Takeba, M. Takeda, A. erla. Takeda, M. eda. T, Takehara, J. Takeno, M. Takeo, M. Takeshima, Y.-i.
180 059,071,281 316, 353 180, 308,325 015,018 043, 148,256 384 254 298 298 370 161 344,360 097,273,380 192 029, 355 084, 100 078, 081, 212, 214, 215, 377, 379, 380 003, 059, 096, 223, 380 167, 273 215 134, 201, 248, 347, 362 324 031, 276 259 144,266 054, 055, 362, 376 142 030,065 284 265 142 140 103,28 1 033 197 174 296
085 150,267 214
Author Index
T
Takhi, M. Taki, H. Takigawa, K.
Tahunas, F.X. Talley, J .J. Talukdar, S. Tam, W. Tamao, K. Tamburini,
M.
Tanabe, K. & Tanaka, A. Tanaka, H. Tanaka, K. Tanaka, M. Tanaka, R. Tanaka, S. Tanaka, W. Tanaka, Y. Tang, K-H. Tang, Y. Tangestaninejad, Tani.
Tani. Taniguchi, Taniguchi,
H. M.
Tanimori, S. Tanino, K. Taniseki, Y. Tao, W.-T. Tarbet, K.H. Tardella, P.A. Tarli, A. . n-0. M Tashtoush, H.I.
S.
268, 269, 372 281 376 090, 194 327 277 299 109 139 203 106 019, 080, 298, 302 223 175 089 045 019 249, 297 013, 293 029 156 080, 209, 236, 298, 302 260 071, 084, 085, 331 161 098 166 072, 135, 214, 246, 326, 351 224, 236, 388 156 251 003, 134, 155, 201, 248, 347, 362 251 020,267, 319 019 186, 275 015 133 235 053, 073 088
433
Tatsukawa, A. Tatsuki, S. Tatsumi, A. Tavares, F. Taylor. P.C. lor. S& Taylor, S.R. Tchitoh, K. Teasdale, A. . 1. R
Teleha, C.A. Tellier. Temperini, A. ten Hoeve, W. Terada, M. Terrett, N.K. Testaferri, L. oulla. F, Thakkar, K. Thanulingam, T.L. Thelland, A. Thiecke, J.R.G. Thies, 0. Thijs, L. Thiruvazhi, M. Thomas, K.L. Thompson, D.F. Thomsen, D.S. Thorimbert, S. Thornton, S.R. Tiecco, M. . 1. M, Toader, D. Tobe, T. 0. n Tohjo, T. Tohma, H. Tohno, I. Tohyama, Y. ok&, M, Tokuda, Y. Tokutake, N. Tollner, K. Tolstikova, L.L Tomaru, J.-i.
273 333 252 316 232 075 159 258 199 212 183 388 244 145 129, 015 125, 145, 305, 337 168 295 129 302 308 354 138 358, 168 110 307 145, 145, 373 153 142 291 161 323 319 127, 030 383 009 157 232
294 383 238 312,350
365
238 238
277
434
T-U
Tomasi, I. Tomasini, F. Tomasoni, L. Tomizuka, J. Tomlinson, G.D. Tomooka, IS. Toneva, R. Tong, L. Tordeux, M. Tori-i, A. Torii.
Totland,K. Touzin, A-M. Towne, T.B. Trehan, A. em. S, Trejo, A. Trepton, B. Trewhella, M.A. Trivellas, A.
Trombini, C. st. B.M
Trotter, B.W. Troupei, M. Trujillo, J.I. Tsai, H.-W. . 1. Y-M& v. s-c,
Tse, C.-L. Tseng, W.-H.
Tsuchimoto, Tsudzuki, K. Tsuii.
T.
220 293, 254 293 076 075 065 282 034 131 356 053 152, 249, 096, 354 106 383 110 260 345 345, 299 379 258 089 081, 169 015 049, 287, 369, 388 366 184 141 237 161 156, 178 365 375 032, 155, 060, 018 178,
Author Index
lIu.iJ 340
177, 189, 297, 307 236, 369
Tsujiguchi, Y. Tsujimoto, M. Tsukazaki, M. Tsukinoki, T. Tsukuda, N. Tsumagari, Y. Tsumura, S. Tsuno, M. a. T, Tsunoi, S. Tsushima, K. Tsutsumi, N. Tsuzuki, H. Tu, C. Tubergen, M.W. Tucker, C.E. Tuladhar, SM. do. P, Turner, K.A. J,
350
107, 154,
064, 083, 299, 367, 377, 379,
373
265 202, 271 144 338, 368
uang, s. Uchida, S. Uchida, T. Uchimam, T. Uchiro, H. Uchiyama, K. ueda, I. Ueda, M. Ueki. elo. M, Uemura, M. Uemur& . . enUeno, M. Ueno, R. Ueno, S. Ueno, Y. uen. D, Ykaii. Ulivi, P. . . am-Ronchl. fJndheim. 1c,
209, 239, 259 276 073 253 148 151 248, 316 052, 302 166 073 122, 175 078, 102 152 197 384 290,
216,311 338,368
362 143, 333
279, 323 209
326
280 298 303 015 325 314 331 055, 261 009 179 001 032, 089, 302 221 073 176 152, 153 073, 096, 236, 369 113,382,385 149 316 015,018,322 103,256,307
u-v-w
Author Index
Unstead-Daggett, J. Uozumi, Y. Urabe, H. Urch, C.J. Urso, A. Usato, F. Usui, K.
Uzan, R.
0.w, Vaid, R.K. Vaino, A.R. VaIenciano, J. Vallecchi, M.E. Vallin, I.M. Valvano, N.L. Van de Weghe, P. Van Der Schoot, M. Van Kateswarlu, S. Van Nieuwenhze, M.S. van der Donk, W.A. der Ge& van Klaveren, M. oten. G, van Leeuwen, P.W.N.M. van Maanen, H.L. Vanderbulcke-Coyette, B. Vanhessche, K.P.M.
Varghese, J.P. Varma, M. a. R& Vasapollo, G. Vdtier. M Vaupel, A. Vazquez, J. Veerapanane, H. Vega, F.R. . eu
388 034, 261 023 092 134, 322 091 032, 059, 190, 251, 307, 263
041, 220,
435
Ventura, M .P. Venugopal, M. Verardo, G. Verdagauer, X.
225
265 096, 214, 273, 359,
187, 223, 274, 380
101 102 047 242 383 366 116 029, 257, 286 301 369 250 039 016,390 019, 125, 288 341 288 319 040 203, 383,387 242 036, 189 009,044,055 009,044,055 008,009 377, 378 355 208 030 026 043. I 206
Verpeaux, J.N. Vetelino, M.G. Vettel, S. Vetter, A.H. Vicart, N. . lehe. HG, Vij, A. Yiin. Vilaplana, M.J. Villemin. D, Virica, J. Viswajanani,
R.
Viziano, M. Voigt, K. Volante, R.P. Volta, M. n Holleben, ruzL, Voronkov, M.G. Vourloumis, D. Voymov, G.H. Vyas, K.A. Waas, J. Wada, E. Wada, M. Wadgaonkar, P.P. Wagner, J.M. Waid, P.P. Wakasa, N. Waldmann, H. Wali, A. Walia, M. Walker, C.
381 115,283 123 265 345 226 226 050,072 016 134 322 306, 319, 365, 375,378 345 288 305 305 005, 141, 196, 273 202 046, 160, 181, 182, 265 101 378 288 135 085 157 235 012 137
184 252 024 047, 060, 135, 211 127 080 012 356 034 205 345 026 103 348
436
Wallace, E.M. Wallach, J. Wallbaum, S. Walsgrove, T. Walsh, P.J. Waker, D.S. alters. m Wan, J.
Wang, D.-K. Wang, G.-Z. Wang, J. Wang, J.Q. Wang, Q. Wang, R.-T. Wang, S.-F. Wang, T. Wang, T.-L. Wang, W.-B. Wang, W.-L. Wang, X. Wang, Y. Wang, Z-M. _Wang. Wang, Z-M. d. A.D, Ward, E.L.M. Ward, S.E. Ware, R. Washiyama, M. assee Watanabe, K. Watanabe, M. Watanabe, N. Watanabe, T. Watanabe, Y. Watase, S. Watrelot, S. Watson, P.S. eavers. ItT, ebu Weber, V. Weglarz, M.A. Wegman, S.
Author Index
W
246 335 015 105 247 347 209 205 034 388 322 188 174, 339 170 143, 161, 239, 360 289, 332 218 370 109, 110 268 190 071, 278 245 190, 250, 328, 334 040, 246 264, 310 053, 143 043 252 292 333,348 061 017 201,330 029, 281 096, 131, 311, 339, 347 365 366 326.327 228, 229 099 226 316
Wegner. G, Wei, Z-Y. Weickhardt, K. Weidner, J.J. Weigerding, M. Weingarten, G.G. Weingarten, M.D. Weinhouse, MI. . Wemreb. S.M.
356
Weis, C.D. Weiss, T.J. Weitz, I.S. Wells, A. Wells, A.P. Wells, C. Wermuth, C.G. Westermann, J.
274,
307, 369
Westenvelle, U. Westman, G. Westrum, L.J. Whang, H.S. Whelan, J. Wheless, K. Whi tbv. R.J, White. J.D, Whitham, G.H. whitiw. A, Whitley, P.E. Whittaker, M.R. Wicemec, C. Wicha. . lemer. D.F. Wietzke, R. Wijaya, N. Wilde, R.G. Wilgus, C.P. . lk. B& Williams II, T.C. WiIliams. D.R, Williams, ID Williams. J.M.J, Williams, L.
361 102, 300 151, 298 034 343 059, 336 009, 298, 137 058 220 384 334 214 380 278 313 089, 093 131 158 119 106, 190 028 124, 147 388, 360 273 258 227 262 359 053 042 168 113 208, 118 253 275 015, 307
103, 116, 153
366 140, 236, 319
091, 092,
180
126 389
210
305
Author Index
Willoughby, CA. Wills. Wilson, D. Wilson, J.G. Wilson, V.P. Winand, R.
437
W-X-Y
098 157 373 039, 156 138, 279 252 213, 074 180 026, 040
Xia, W. Xiaohui, 2. Xie, L. Xiong, H. xu, c. Xu, D.
Wynberg, H.
123 031 203 253 175 023 313 043 038, 213, 214, 280 181 176 127 233 019 380 210 210 168 123 259 088 031, 249 382 368 263 079, 146 340 360 094 028 237 104 025,086, 137, 206 067 189 175 183 106 271 316 176 129, 294
Xi, 2.
214, 379
Yamamura, IS.
Winter, S.B.D. m Wirth, D.D. Wise, L.D. Wishka, D.G. WiSiewski, W. Wissing, E. Witulski, B. Wlostowski, M. wo, s. Wong, M.-K. Wong, Y.-S. 00. s%& Wood, M.R. Woodall, T.M. Worrall, J.M. Wos, J.A. Wrigglesworth, R Wright. S.W, Wu, G. Wu, J. Wu, J.H. Wu, M.-C. u. M.-L wu, s. u. S.-H,
wu, x. Wu, X.-M. wu, 25 ulff. WD, Wuonola,M.A. Wurster, J.
Xu, xu, xu, xu, u. xu,
F. w. W.-X. Y. Y.-C, 2.
Yadav, J.S. Yajima, T. Yakahashi, K. Yakai, T. Yamada, H. Yamada, M. Yamada, N.
Yamagata, T. Yamaguchi, J. . chi. M, Yamaguchi, S. Yamaguchi, T. Yamaguchi, Y. Yamamiya, Y. -A. 0t0.
n
Yamamoto, J. oto. Y,
339 246, 252,
280
341
281 349 015,019,317 049 166 159 013, 059, 266, 378, 380 209 034, 163, 164, 165,166, 167, 231, 390 135, 326 103, 179 241, 283, 368, 369 273 061 090 236, 383 144 007, 257 019, 022, 052, 092, 159, 194, 200, 268,269, 274, 279, 293, 346, 377,380 131 025, 194, 253, 257, 289, 315, 334, 374,375 021
438
Y
Yamanaka, Yamanami, Yamasaki, Yamashita,
H. A. H. F.
Yamashita, T. Yamashita, Y. Yamazaki, C. Yamazaki, H. Yan, D.-S. Yanada, K. Yanagi, T. Yanagisawa, A.
au Yang, Yang, Yang,
D, D.T.C, H. J.
Yang, J.-F. Yang, K. Yang, Q. Yang, R.-Y. Yang, T.-K, Yang. Yang, 2. Yanigiya, N. Yao, Q. Yao, X.-B. Yaouanc, J.J. zhond Yarbcrry, D.J. Yasuda, M. Yasue, H. Yasue, K. Yasui, K. Yato, M. Yavcui. Ye, J. Yelamaggad C.V. Yep, G.L. Yet, L.
065, 266, 324 254 095 081 085, 262 216 114, 115, 231, 314 030 286, 299, 333 013 237 047,086,222 047,086, 222 041,220 348 019, 022, 052, 377, 380 139 168 008 188,319 205 149 056 179 310 030 055 204 008, 112, 334 305 194 025 120 016 136 237, 308 183 022, 052, 380 019 182 237 020, 331 046, 181, 182 156 281
Author Index
Yeunu Yip, Y.-C. Yli-Kauhaluoma, Yokoo, T. Yokota, K. 0-M.&
Yokoyama, S. okozawa T, Yoneda, T. Yonezawa, S. Yonezawa, Y. oon. N.M,
Yoon, Y.J. York, C, Yorozu. K, Yoshida, A. Yoshida. J, Yoshida, S. Yoshida, Y. Yoshihara. K, Yoshimune, M. Yoshioka, M. Yoshizawa, T. Young, A.R. Young, Y.M. Yu, C.-M. Yu, J. Yu, L. Yu, s. Yu, Y. Yuan, K. Yuan, S. Yuasa, M. Yuk, J.Y. Yuki, T. Yuki, Y. Yulin, J. Yum, E.K. Yun, M. Yuncheng, Y.
J.T.
028 168 071 187 055 142 379 369 232 303 013, 026, 086, 110, 135, 136, 181, 236 046 191, 356 034, 166, 189, 379 054, 272 085 045, 194 287 063 307 324 125 201 283 045, 083, 381 250 030 170, 206, 364, 369 066 198 237 158 367 049,144 149, 157 104, 105, 188 325 149, 157
048, 118, 161,
167
234,
327,
122,
Author Index
Yvanaeff, C. Yyas, K.A.
Zaidi, S. Zajac, N. Zakett, D. Zaltsgendler, I. Zanardi, G. Zanirato, V. Zanti, P. Zarcone, L.M.J.
Zargarian, D. Zdravkovski, Z. Zeng, H. =ng, Q. Zenner, J.M. Zepp, C.M. Zevaco, T. Zhang, H-C. Zhang, H. Zhang, J. Zhang, K. Zhang, L-T. Zhang, W. Zhang, W.-Y. Zhang, X-L.
Zhang, X.-L.
zhang, 2. Zhang, Z.J.
439
020, 120, 250, 262, 141 149
146 193 179 255 131 128 250 162 046 104, 123 246 100 356 204 290 301 032 007 077 205 258 311 236 067, 204 295 245 037, 317 275 028, 080, 206, 327, 369 170 190 224
039, 099, 174, 247, 25 1, 254, 276
105, 118,
083, 200,
163, 312,
076, 170, 221, 350,
076, 180, 278, 364,
Zhao, Ii. Zhao. Zhao, Y. Zheng, B. Zheng, D. Zheng, G.Z. Zheng, J. Zheng, L. Zhi, L. Zhong, B. Zhong, H.M. Zhou, J.-Y. Zhou, J.J.P. Zhou, M. Zhou, R. Zhou, T. Zhou, Z. Zhou, Z.-L. Zhu, D. Zhu, G. Zhu, L. Zhu, Q.-C. Zhu, Z. 7,ieger. H.E. Ziegler Jr., C.B. Zini, CA. Zlokazov, M.V. Zondervan, C. Zucolotto, M. Zupan, M. wanenburg, B, Zyk, N.V.
101 218, 085 023, 355, 207 350 338 156 388 275 007, 025 275 361, 028 361 216 098 329 340 028 067 052, 184 210 385 085 054 151 085 342 308 356
342 133, 190, 358
365
362
137
