Organic Synthesis: The Disconnection Approach

Organic Synth岱is: The Disconnection Approach

Organic Synth臼is; The Disconnection Approach 2日d Edition Stuart 飞毛Tarre室主 u瓦

Department, and

Paul Wyatt Schoolof

of Bristol ,

⑧WIL盯 AJohn 飞iVìley and Sons, Ltd" Publication

U瓦

This edition first published 2008 2008 John 飞的 ley & Sons , Inc.

Registered 01.声 & Sons

John 皆iley

Ltd， τhe

Atrium , Southem Gate.

Chichester，有部 t Suss帜，

P019

8S龟 United

Kingdom

For details of our global 时itorial offices , for customer services and for infonnation about how to apply for permission to 陀use the copyri在ht material in this book please see our website at www.wiley.com. τhe

right of the author to be identified as the author of this work has been asserted in accordance with the Copyright , Desi 盯1S and Patents Act 1988. A l\ rights reserved. N 0 P缸t of this publication 部ay be reproduced , stored in a retrieval system , or transmitted , in by any fom1 or by any means , electronic , mechanical , photocopying , recording or otherwise , exc巳pt as the UK Copyright , Designs and Patents Act 1988 噎 without the prior permissíon of the publisher. 认Tiley

also publishes its books in a variety of electronic formats. Some content that appears in print may not be avaHable in electronic books. Designations used by companies to distinguish their products are often daimed as trademarks. AH brand names and product names used in this book are trade 凶m时， service marks , trademarks or registered trademarks of their respective owners The publìsher is not associated with any product or v念ndor mentioned in this book. 丁his publicatìon is designed to accurate and authoritative information in regard to the subject matter covered. It is sold on the understanding that the publisher is not engaged in rendering professional services. If advice or other expert 揣在 istance is require丛 the services of cornpetent professional should be sough t. ‘

The publísher and the author make no representations or warranties with respect to the accuracy or cornpleteness of the contents of this work and 呼机ifically disclai 凯 all warranties , without limitation any implied warranties of 岳tness for a particular purpose. This work sold with the understanding that the pubhsher is not services. τhe ad飞忧e and strategies contained herein rnay not be suitable for engaged in rendering every situation. In view of ongoing research , equiprnent modifications , changes in govemmental regulation笃， and the constant fiow of information relating to the use of experimental reagents , equipment警 and devices , the reader is u塔ed to review and evaluate the information provided in the packagεinsert or instructions for each chemical , piece of equipment , reagent , or device for , arno只 g other things ‘ any changes in the instructions or índication of usage and for added wamings and precautions. The fact that an organization or Website is referred to in this work as a citation andJor a potential source of further informatìon does not mean that the author or the publisher endorses the information the organization or Website may pro飞lide or recornmendations it may rnake. Furth时， readers should be aware that Internet Websites listed in this work may have changed or disappeared betw四只 when this work was written and when it is re我d. No waπanty may be created or extended by any promotional statements for this work. Neither the publisher nor the author shall be liable for any damages arising herefrom. LibraηI

0/ Congress

C.αtaloging-in-Pl￥blication

Data

Warren哩 Stuart

G. Organic synthesís : the disconnection approach I Stuart Warren and Paul p. cm. Includes biblíographical references and index. ISBN 978-0-470-71237-5 (cloth)一-ISBN 978-0斗70-71236-8 (pbk. : alk. paper) 1. O~mic L 百yatt， PauL n. 在tle. QD262.W2842008 547'.2-dc22

Wyatt.一一 2nd

ed.

2008033269 A catalogue record for this book is available from the British ISl日-l' 978-0-470-7份 12375 (HIB)

τypeset

978-0-470平 12368

(P!B)

in 10/12 Times-Roman by Laserwords Private Li mited , Chennai , India Printed and bound in Great Britain by CPI Antony Rowe, Chippenham, Wiltshire

&zt

的部

gLvr

主

C

a

巨

Marria口，… 2007 ，

stc LHa , se ih c(adi t

飞在rho

7￥&'也

ac

拿雹霉 -A

first Marrian

to

Co吕立f盟ts

Preface

lX

General References

XI

2. 3. 4. 5. 6. 7. 8.

Basic and Strategy 1: The Order of Events One-Group C-X Dìsconnections Strate 2: v II: C-X DisconnectÎ ons III: Reversal of Polarity ,

7730J5531 li23345867

Synthesis of Aromatic

of

Arnìn已

生 Strategy IV: Protecting 10. One Group C C Disconnections 1: Alcohols 11. General St栩如前r A: a Disconnection 12. Strate玄v V: …

VII: 盯se

22.

X:

技itro

23. 在NφGroup Disconnections IV: Compounds 24. Disconnections V: 25. 26. Strategy XII: Reconnection 27. Two-Group C…C Disconn巳ctions VI: 28. General B: Strategy of Car七onyl Disconnections 29. XIII: Introduction to Synthesis: Saturated 30. Three品lernbered XIV: 3 1.

'1

18. 19. 20. 21.

豆

(Alkynes) of C…C Disconnections 1: Diels-Ald时 Reactions Strate 2: v VIII: Introduction to 在isconnections II: Compounds IX: Control in Car柱。nvl Condensations C-C Disconnections III: Compounds Conjugate (Michael) Addîtion and Robinson Annelation

17.τwo-Group

212i$1·EAli2·

15. Alkene 16. Strategy

151 161 167 177 185 193 199 207 217 229 237 245

Contents

VH呈

33. XV:τhe Use of Ketenes in 34. Five-Mem如 ered 35. Strate Q. v XV I:

251 255 Special Methods 2岳 1

36. 37. 38. 39. 40.

Six-Membered Rings General Strategy C: XVII: AromatÍC D:A母 vanced General

Index

Synthesis

269 279 289 301 313 325

Preface publìshed Organic 1于ze Disconnection Approach 色y Stuart to the learning of synthesis has become while the book Ìtself is now dated in content and appearance ‘ In 唱Tiley published Organic and Control by Paul Wyatt and Stuart 轧Tarren. Thís muc如柱。ok ís as a fourth year und巳 rgradu时es and research workers in universities and industry. The workbook was published ìn 2008.τ如is new book made thεold one look very dated ín and content and gaps between what students were expectεd to understand in the 1980s to understand now. This second edition is intended to fill some of and what are those gaps. The of the book is the same in the second edítion. It alternates chapters new concepts wÌth strategy chapters that put 出e new work in the context of overall planning. 丁he 40 chapters have the same titles: some have hardly been changed whíle others have a revision with considerable amounts of new m剖erial. In most cases from recent years are included. in the pharmaceutical One source of new material is the courses 出at the authors Our 色asic course is 'The Disconnection Approach' and the 削aterial we have for this of the various compounds course has reinforced our attempts to reasons for the for students. We to which we 忧 lieve enlivens the 加ok and makes it more after the publication of the a second edítíon of the workbook The 民rst edition of th巳 textbook was in fact thεthird in a series of 品。oks on by 乳 The firs t: The an lntroduction to 如 1974 ， is a book asking for a of interaction with the reader who was to solve pro剖ems while rarely use now as the method has 岳阳 n suplersedt~d 七 y interactive programmes on computers. Paul Wyatt is writín革 an electronic book to replace The Cα rbonyl Group which will a of an electronic 七ook and 七ooks with associated workbooks in a uniform format that we hope will prove of value as students of organic develop their careers.

In the 26 years

since 有iley

Warren ，由自 approach

Stuart

飞可arren

and Paul 研rya生在 March 2008.