Enantiomer Separation
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1 Enantiomer Separation
2 Enantiomer Separation Fundamentals and Practical Methods Edited by Professor of Chemistry, Department of Chemistry, Okayama University of Science, Japan KLUWER ACADEMIC PUBLISHERS DORDRECHT / BOSTON / LONDON
3 A C.I.P. Catalogue record for this book is available from the Library of Congress. ISBN (HB) ISBN (e-book) Published by Kluwer Academic Publishers, P.O. Box 17, 3300 AA Dordrecht, The Netherlands. Sold and distributed in North, Central and South America by Kluwer Academic Publishers, 101 Philip Drive, Norwell, MA 02061, U.S.A. In all other countries, sold and distributed by Kluwer Academic Publishers, P.O. Box 322, 3300 AH Dordrecht, The Netherlands. Printed on acid-free paper All Rights Reserved 2004 Kluwer Academic Publishers No part of this work may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, microfilming, recording or otherwise, without written permission from the Publisher, with the exception of any material supplied specifically for the purpose of being entered and executed on a computer system, for exclusive use by the purchaser of the work. Printed in the Netherlands.
4 Table of Contents Preface vii Optical resolutions by inclusion complexation with a chiral host compound 1 Crystalline dipeptides: their molecular recognition to be useful to enantiomer separation 49 Katsuyuki Ogura, Motohiro Akazome Optical resolution via complex formation with O,O -dibenzoyltataric acid 73 Ferenc Faigl, Dávid Kozma Spontaneous chiral crystallization of achiral materials and absolute asymmetric transformation in the chiral crystalline environment 103 Masami Sakamoto Preferential enrichment: a dynamic enantiomeric resolution phenomenon caused by polymorphic transition during crystallization 135 Rui Tamura, Takanori Ushio Optical resolution by means of crystallization 165 H. Nohira, K. Sakai Lipase-catalyzed kinetic resolution of racemates: a versatile method for the separation of enantiomers 193 Ashraf Ghanem Enzymatic kinetic resolution 231 Kaoru Nakamura, Tomoko Matsuda Preparative-scale separation of enantiomers on chiral stationary phases by gas chromatography 2 7 Volker Schurig Practical resolution of enantiomers by high-performance liquid chromatography 301 Chiyo Yamamoto, Yoshio Okamoto Index 323 v
5 PREFACE In spite of important advances in asymmetric synthesis, chiral compounds cannot all be obtained in a pure state by asymmetric synthesis. As a result, enantiomer separation remains an important technique for obtaining optically active materials. Although asymmetric synthesis is a once-only procedure, an enantiomer separation process can be repeated until the optically pure sample is obtained. This book discusses several new enantiomer separation methods using modern techniques developed by experts in the field. These methods consist mainly of the following three types: 1) Enantiomer separation by inclusion complexation with a chiral host compound 2) Enantiomer separation using biological methods 3) Enantiomer separation by HPLC chromatography using a column containing a chiral stationary phase. Separation of a racemic compound has been called optical resolution or simply resolution. Nowadays, the descriptions enantiomer resolution or enantiomer separation are also commonly used. Accordingly, Enantiomer Separation is used in the title of this book. The editor and all chapter contributors hope that this book is helpful for scientists and engineers working in this field. Okayama, March 2004 vii
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