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Roger A. Sheldon - Chirotechnology

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This reference provides an introduction to the phenomenon of chirality and its importance in conjunction with biological activity and offers an easy-to-read examination of practical, industrially relevant methods for the synthesis of optically active compounds.;Furnishing hands-on guidelines for the development of economically viable synthetic compounds, Chirotechnology: explains optical isomerism and stereochemistry; gives a general overview of various methods of synthesis; supplies detailed explications of specific techniques, including fermentation, crystallization, the chirality pool, enzymatic methods, and catalytic asymmetric synthesis; illustrates and compares approaches with examples taken directly from industry such as the synthesis of pharmaceuticals, agrochemicals, flavours, and fragrances; and clarifies the importance of determining which approach to use for the synthesis of particular molecules.;With over 1100 literature citations, tables and figures, Chirotechnology is a reference for chemical engineers; industrial, organic and medicinal chemists; and bioprocess technologists, as well as a text for upper-level undergraduate, graduate and continuing-education students in these disciplines.

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title Chirotechnology Industrial Synthesis of Optically Active Compounds - photo 1

title:Chirotechnology : Industrial Synthesis of Optically Active Compounds
author:Sheldon, Roger A.
publisher:CRC Press
isbn10 | asin:0824791436
print isbn13:9780824791438
ebook isbn13:9780585157184
language:English
subjectOptical isomers--Biotechnology, Chiral drugs--Biotechnology.
publication date:1993
lcc:TP248.65.O65S44 1993eb
ddc:660/.63
subject:Optical isomers--Biotechnology, Chiral drugs--Biotechnology.
Page i
Chirotechnology
Industrial Synthesis of Optically Active Compounds
Roger A. Sheldon
Delft University of Technology
Delft, The Netherlands
Marcel Dekker, Inc.
New YorkBaselHong Kong
Page ii
Library of Congress Cataloging-in-Publication Data
Sheldon, Roger A.
Chirotechnology : industrial synthesis of optically active
compounds / Roger A. Sheldon.
p. cm.
Includes bibliographical references and index.
ISBN 0-8247-9143-6 (alk. paper)
1. Optical isomers--Biotechnology. 2. Chiral drugs--Biotechnology. I. Title.
TP248.65.065S44 1993
660'.63--dc20Picture 2 93-18852
CIP
The publisher offers discounts on this book when ordered in bulk quantities. For more information, write to Special Sales/Professional Marketing at the address below.
This book is printed on acid-free paper.
Copyright 1993 by MARCEL DEKKER, INC. All Rights Reserved.
Neither this book nor any part may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, microfilming, and recording, or by any information storage and retrieval system, without permission in writing from the publisher.
MARCEL DEKKER, INC.
270 Madison Avenue, New York, New York 10016
Current printing (last digit):
10 9 8 7 6 5 4 3 2
PRINTED IN THE UNITED STATES OF AMERICA
Page iii
To
Jetty,
Annemarie
and Frank
Page v
Foreword
Only a few people are able to present the topic of chirotechnology from both its academic and industrial sides. The academic side cannot be neglected because of the fundamental nature of chirality and its longstanding influence on the thinking of chemists. The other side, the industrial approach, has come into its own during the past ten years as purity and safety regulations have swamped the chemical industry. Roger Sheldon, formerly a Shell chemist and Andeno-DSM research director and presently Professor of Organic Chemistry at the University of Delft, is one of the few people who can handle this multifaceted task. He has done so in this excellent book, whose time has come.
The reader will come away with a new understanding not only of the importance of chirality as a dominating factor in the preparation of new drugs, but also of new reagents, conditions, catalysts, mechanisms, and syntheses. These are presented in a manner that allows even the inexperienced student to separate the useful from the merely exotic. The masters of our art, the role models in organic synthesis, are often those who have perfected the art of "total synthesis" of complex natural products containing upward of a dozen stereocenters. It is not surprising that many students complete their studies in organic chemistry with the notion that fame and fortune lie at the end of the "total synthesis" rainbow. Little do they realize that the successful preparation on an industrial scale of a totally synthetic (enantiomerically pure) new drug may require six months of laboratory scale synthesis and three years of process development work. Modesty demands us to admit that
Page vi
synthetic transformations that were perfected and scaled up at the end of the last centurysuch as classical resolutions, oxidations and reductions, esterifications and hydrolyses, and substitutions and eliminationshave lost none of their importance today, despite novel solvents, catalysts, crown ethers, and silicon-protecting groups.
The value of the contribution of Professor Sheldon's book to the literature of synthetic organic chemistry lies to a large extent in this aspect of the art. Professor Sheldon has been there and has seen what it takes to make enantiomerically pure compounds on a ton scale. He introduces the reader to the reality of organic preparationsof an important class of compoundsnot as an idle curiosity published as a prestigious communication to the editor, but as a procedure of value to the plant manager.
In addition to the obvious value of this monograph to organic chemists everywhere, the educational value of this book should not be underestimated. Written in understandable prose and in an entertaining style, this book will prove of great value for advanced undergraduate and graduate students.
On a more personal note, I wish to thank Professor Sheldon for giving me the opportunity to speak my piece on the value of this book. I have known the author as research director and colleague for more than a dozen years and I have valued his friendship. The author's thorough knowledge of all phases of organic chemistry, his enthusiastic leadership, and his productive career have crystallized in this valuable monograph. I wish him all of the success he has surely earned.
Picture 3
HANS WYNBERG
EMERITUS PROFESSOR OF ORGANIC CHEMISTRY
GRONINGEN, THE NETHERLANDS
Page vii
Preface
Optically active compounds are ubiquitous in our everyday lives. They are the active constituents of many medicines, vitamins, flavors and fragrances, and the herbicides and pesticides used in crop protection. Indeed, the essential components of life itselfproteins, carbohydrates, and DNAare constructed from optically active building blocks.
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