H. U. Blaser, E. Schmidt (Eds.) Asymmetric Catalysis on Industrial Scale
Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions Edited by H. U. Blaser, E. Schmidt Copyright ° 2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN: 3-527-30631-5
Further Reading from Wiley-VCH Aehle, W.
Enzymes in Industry, 2. Ed. 2003. ISBN 3-527-29592-5 Weissermel, K., Arpe H.-J.
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Research & Development Management in the Chemical and Pharmaceutical Industry, 2. Ed. 2003. ISBN 3-527-30667-6 Cornils, B., Herrmann, W. A.
Applied Homogeneous Catalysis with Organometallic Compounds, 3 Vols., 2. Ed. 2002. ISBN 3-527-30434-7
Asymmetric Catalysis on Industrial Scale Challenges, Approaches and Solutions Edited by H. U. Blaser, E. Schmidt
Editors Dr. Hans-Ulrich Blaser Solvias AG P.O. Box CH-4002 Basel Switzerland
[email protected] Dr. Elke Schmidt Syngenta Crop Protection AG CH-4058 Basel Switzerland
[email protected]
n This book was carefully produced. Nevertheless, editors, authors and publisher do not warrant the information contained therein to be free of errors. Readers are advised to keep in mind that statements, data, illustrations, procedural details or other items may inadvertently be inaccurate.
Library of Congress Card No.: applied for British Library Cataloguing-in-Publication Data A catalogue record for this book is available from the British Library. Bibliographic information published by Die Deutsche Bibliothek Die Deutsche Bibliothek lists this publication in the Deutsche Nationalbibliografie; detailed bibliographic data is available in the Internet at
° 2004 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany All rights reserved (including those of translation in other languages). No part of this book may be reproduced in any form ± by photoprinting, microfilm, or any other means ± nor transmitted or translated into machine language without written permission from the publishers. Registered names, trademarks, etc. used in this book, even when not specifically marked as such, are not to be considered unprotected by law. Printed in the Federal Republic of Germany Printed on acid-free paper Composition K+V Fotosatz GmbH, Beerfelden Printing betz-druck GmbH, Darmstadt Bookbinding J. Schåffer GmbH & Co. KG, Grçnstadt ISBN
3-527-30631-5
V
Contents List of Contributors Introduction
XXI
1
Hans-Ulrich Blaser and Elke Schmidt 1 Background and Motivation 1 2 Goals and Concept 1 3 Our (the Editors) Assessment of the Resulting Monograph 2 4 The Organization of the Book (Types of Intermediates ± Catalysts ± Situations) 3 4.1 Category: New Processes for Existing Active Compounds 5 4.2 Category II: New Catalysts and/or Processes for Important Building Blocks 5 4.3 Category III: Adaptation of Existing Catalysts for Important Building Blocks 6 4.4 Category IV: Processes for New Chemical Entities (NCE) 6 5 Missing Processes 6 6 Some Important Messages 9 6.1 Transformations and Catalyst Types 10 6.2 Scale, Development Stage 13 6.3 Synthesis Planning and Time Lines 13 6.4 Major Technical Problems 14 6.5 Technology and Patents 14 7 Final Comments and Conclusions 15 8 Glossary 16 9 References 18
VI
Contents
I
New Processes for Existing Active Compounds
1
Asymmetric Hydrogenations ± The Monsanto L-Dopa Process
1.1 1.2 1.3 1.4 1.5 1.6
William S. Knowles The Development of Chiral Phosphane Ligands