Handbook of chiral chemicals PDF
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Handbook of Chiral Chemicals S e c o n d E d i t i o n © 2006 by Taylor & Francis Group, LLC Handbook of Chiral Chemicals S e c o n d E d i t i o n edited by D a v i d A g e r Boca Raton London New York A CRC title, part of the Taylor & Francis imprint, a member of the Taylor & Francis Group, the academic division of T&F Informa plc. © 2006 by Taylor & Francis Group, LLC Published in 2006 by CRC Press Taylor & Francis Group 6000 Broken Sound Parkway NW, Suite 300 Boca Raton, FL 33487-2742 © 2006 by Taylor & Francis Group, LLC CRC Press is an imprint of Taylor & Francis Group No claim to original U.S. Government works Printed in the United States of America on acid-free paper 10 9 8 7 6 5 4 3 2 1 International Standard Book Number-10: 1-57444-664-9 (Hardcover) International Standard Book Number-13: 978-1-57444-664-7 (Hardcover) Library of Congress Card Number 2005043716 This book contains information obtained from authentic and highly regarded sources. Reprinted material is quoted with permission, and sources are indicated. A wide variety of references are listed. Reasonable efforts have been made to publish reliable data and information, but the author and the publisher cannot assume responsibility for the validity of all materials or for the consequences of their use. No part of this book may be reprinted, reproduced, transmitted, or utilized in any form by any electronic, mechanical, or other means, now known or hereafter invented, including photocopying, microfilming, and recording, or in any information storage or retrieval system, without written permission from the publishers. For permission to photocopy or use material electronically from this work, please access www.copyright.com (http://www.copyright.com/) or contact the Copyright Clearance Center, Inc. (CCC) 222 Rosewood Drive, Danvers, MA 01923, 978-750-8400. CCC is a not-for-profit organization that provides licenses and registration for a variety of users. For organizations that have been granted a photocopy license by the CCC, a separate system of payment has been arranged. Trademark Notice: Product or corporate names may be trademarks or registered trademarks, and are used only for identification and explanation without intent to infringe. Library of Congress Cataloging-in-Publication Data Handbook of chiral chemicals / edited by David J. Ager.—2nd ed. p. cm. Includes bibliographical references and index. ISBN 1-57444-664-9 (alk. paper) 1. Chemicals—Handbooks, manuals, etc. 2. Enantiomers—Handbooks, manuals, etc. I. Ager, David J. TP201.H26 2005 661'.8--dc22 2005043716 Visit the Taylor & Francis Web site at http://www.taylorandfrancis.com Taylor & Francis Group and the CRC Press Web site at is the Academic Division of Informa plc. http://www.crcpress.com © 2006 by Taylor & Francis Group, LLC Contents Chapter 1 Introduction...................................................................................................................1 David J. Ager Chapter 2 Amino Acids...............................................................................................................11 David J. Ager Chapter 3 Microbial Pathway Engineering for Amino Acid Manufacture................................31 Ian Fotheringham and Paul P. Taylor Chapter 4 Carbohydrates in Synthesis........................................................................................47 David J. Ager Chapter 5 Terpenes: The Expansion of the Chiral Pool.............................................................59 Weiguo Liu Chapter 6 Resolutions at Large Scale: Case Studies..................................................................75 Weiguo Liu Chapter 7 New Developments in Crystallization-Induced Resolution.......................................97 Bernard Kaptein, Ton R. Vries, José W. Nieuwenhuijzen, Richard M. Kellogg, Reinier F. P. Grimbergen, and Quirinus B. Broxterman Chapter 8 The Role of cis-1-Amino-2-Indanol in Resolution Processes.................................117 Chris H. Senanayake, Dhileepkumar Krishnamurthy, and Isabelle Gallou Chapter 9 Asymmetric Oxidations............................................................................................123 David J. Ager and David R. Allen Chapter 10 Asymmetric Epoxidation of Olefins by Chiral Ketones..........................................147 Yian Shi Chapter 11 Ozonolysis in the Production of Chiral Fine Chemicals.........................................165 Janine McGuire, Gary Bond, and Peter J. Haslam © 2006 by Taylor & Francis Group, LLC Chapter 12 Transition Metal Catalyzed Hydrogenations, Isomerizations, and Other Reactions........................................................................................................185 Scott A. Laneman Chapter 13 Modular, Chiral P-Heterocycles in Asymmetric Catalysis......................................249 Mark J. Burk and James A. Ramsden Chapter 14 Asymmetric Olefin Hydrogenation Using Monodentate BINOL- and Bisphenol-Based Ligands: Phosphonites, Phosphites, and Phosphoramidites........269 Johannes G. de Vries Chapter 15 Asymmetric Catalytic Hydrogenation Reactions with Ferrocene-Based Diphosphine Ligands................................................................................................287 Hans-Ulrich Blaser, Matthias Lotz, and Felix Spindler Chapter 16 Asymmetric Reduction of Prochiral Ketones Catalyzed by Oxazaborolidines......305 Michel Bulliard Chapter 17 cis-1-Amino-2-Indanol-Derived Ligands in Asymmetric Catalysis........................319 Chris H. Senanayake, Dhileepkumar Krishnamurthy, and Isabelle Gallou Chapter 18 Enantioselective Hydrogenation of Activated Ketones Using Heterogeneous Pt Catalysts Modified with Cinchona Alkaloids......................................................345 Martin Studer and Hans-Ulrich Blaser Chapter 19 Biotransformations: “Green” Processes for the Synthesis of Chiral Fine Chemicals.........................................................................................359 David P. Pantaleone Chapter 20 Combining Enzyme Discovery and Evolution to Develop Biocatalysts.................405 Mark Burk, Nelson Barton, Grace DeSantis, William Greenberg, David Weiner, and Lishan Zhao Chapter 21 One-Pot Synthesis and the Integration of Chemical and Biocatalytic Conversions...............................................................................................................419 Paul A. Dalby, Gary J. Lye, and John M. Woodley Chapter 22 Substitution Reactions..............................................................................................429 David J. Ager © 2006 by Taylor & Francis Group, LLC Chapter 23 Industrial Applications of Chiral Auxiliaries...........................................................443 David R. Schaad Chapter 24 The Role and Importance of cis-1-Amino-2-Indanol in Biological Systems and Asymmetric Processes........................................................................457 Chris H. Senanayake, Dhileepkumar Krishnamurthy, and Isabelle Gallou Chapter 25 Enantiopure Amines by Chirality Transfer Using (R)-Phenylglycine Amide.........................................................................................487 Ben de Lange, Wilhelmus H. J. Boesten, Marcel van der Sluis, Patrick G. H. Uiterweerd, Henk L. M. Elsenberg, Richard M. Kellogg, and Quirinus B. Broxterman Chapter 26 Pericyclic Reactions.................................................................................................503 Michael B. East Chapter 27 Asymmetric Free-Radical Reductions Mediated by Chiral Stannanes, Germanes, and Silanes.............................................................................................531 Jens Beckmann, Dainis Dakternieks, and Carl H. Schiesser Chapter 28 Metathesis Reactions................................................................................................539 David R. Allen Chapter 29 Synthesis of Homochiral Compounds: A Small Company’s Role..........................559 Karen Etherington, Ed Irving, Feodor Scheinmann, and Basil Wakefield Chapter 30 Commercial Synthesis of the Antiglaucoma Prostanoid Travoprost.......................573 Martin Fox, Mark Jackson, Ian C. Lennon, and Raymond McCague Chapter 31 Synthesis of Large Volume Products.......................................................................589 David J. Ager and Colin R. Bayley © 2006 by Taylor & Francis Group, LLC Preface The purpose of this book is to highlight the problems associated with the production of chiral compounds at a commercial scale. With the movement by pharmaceutical companies to develop single enantiomers as drug candidates, the problems associated with this subclass of organic synthesis are being highlighted. As the stereogenic center can be derived from nature through the use of “chiral pool” starting materials, the major classes of natural products are discussed. Despite the explosion of asymmetric methods in the past 20 years, very few can be performed at scale due to cost, thermodynamic, or equipment limitations. The major reactions that have been used are covered. Resolution, whether chemical or enzymatic, still holds a key position. However, this is changing as highlighted by a short discussion of the best-selling compounds of 2002 compared to 1996. The most mature chemical method for large-scale asymmetric synthesis is hydrogenation. This is highlighted by chapters on the uses of new ligands for hydrogenation as well as hydride reducing agents. Although we have made considerable advances in this area, the general catalyst is still elusive. Although the struggle goes on to identify the ultimate hydrogenation catalyst, for example, the use of enzymes and biological systems for the production of chiral compounds continues to increase at an incredible rate. Now that we have learned to manipulate nature’s catalysts, this area will continue to grow and become more important in the production of fine chemicals. The chapters have been grouped by topic, as shown in the table of contents. The first chapter under a topic heading is a general introduction to that topic. These chapters are not intended to be comprehensive reviews, but to critically discuss the options available at scale. The first chapter of the book is a general introduction. Chapters 2 through 5 discuss how the key subclasses of the chiral pool are obtained. The amino acid chapters are more specific as there are other examples of amino acid syntheses contained within other chapters. The next 23 chapters cover methods that can be used to introduce or control stereogenic centers. In some cases, such as asymmetric hydrogenations, the approach is well established and has been employed for the large-scale synthesis of a number of commercially important compounds. In other cases, such as pericyclic reactions, the potential is there—it just has not been used. Two of these chapters cover enzymatic methods, and this area seems to be more important as we understand how to manipulate enzymes to allow them to catalyze new reactions or take new substrates. The rush to market for pharmaceutical companies is forcing the chemical development time to be minimized. This is leading to large-scale usage of chiral auxiliaries. The chapters on resolution have a number of examples as illustrations. This methodology is still important to obtain chiral compounds. Although, ultimately, it may not be the most cost-effective method, it can provide material in a rapid manner, and can usually be scaled up. The introduction of large-scale chromato- graphic techniques, as well as the availability of a large number of enzymes that can be used to perform reactions on only one enantiomer, will ensure that this approach remains a useful tool in the future. The remaining chapters discuss various examples and topics to augment other chapters and provide a perspective of the different methods available. In two cases, ozonolysis and metathe- sis, the technique need not directly introduce a new stereogenic center. They are, however, still important reactions in the asymmetric context. The final section of the book has three chapters that illustrate applications of the methodologies to prepare specific compounds. One chapter is from a small company and describes a number of projects; the second, from a large company for the synthesis of a relatively small volume product. The final chapter covers large monetary value products. © 2006 by Taylor & Francis Group, LLC If the reader thinks that topics are missing, or if there seems to be a company bias, all major fine chemical manufacturing companies were invited to submit chapters. Even if a methodology has not been specifically covered in depth, the introduction chapter to the topic will most likely contain a reference to follow for further reading. This is the second edition of this book. The publishers asked me whether they should print more of the first edition, or if I was willing to produce a second edition. I chose the latter course. All chapters have been updated, some very significantly illustrating the speed of development in this area. Additional chapters have also been added to highlight successes of the approaches in an industrial setting. I would like to thank all the contributors to this book. Some have had to wait patiently for other contributors to catch up. I would especially like to thank my former colleagues from NSC Technologies for writing and updating many of the chapters that are overviews. They have also supplied numerous suggestions and ideas (and supported the hypothesis that the number of ideas generated is directly proportional to beer consumption). I would also like to make special mention of my new colleagues at DSM, who responded to my requests without hesitation and also provided a number of useful suggestions and ideas. To all the contributors, thanks; this book could not have been completed without you. Dave Ager Raleigh, North Carolina © 2006 by Taylor & Francis Group, LLC The Editor David Ager was born in Northampton, England, in 1953. He received a B.Sc. from Imperial College, London, and a Ph.D. from the University of Cambridge, working with Dr. Ian Fleming on orga- nosilicon chemistry. In 1977 he was awarded a Science Research Council Postdoctoral Fellowship that allowed him to collaborate with Professor Richard Cookson FRS at the University of Southamp- ton. In 1979, he joined the faculty of the University of Liverpool as a Senior Demonstrator. This was followed by an assistant professor position at the University of Toledo in Ohio. In 1986, he joined the NutraSweet Company’s Research and Development group, and became responsible for the scale-up of new sweetener development candidates as a Monsanto Fellow. He is a founding member of NSC Technologies, which became an independent unit of Monsanto in 1995 as part of Monsanto Growth Enterprises. In 1999, NSC was sold to Great Lakes Fine Chemicals; Dr. Ager was a Fellow with GLFC, responsible for the development of new synthetic methodology. After leaving GLFC he worked as a consultant on chiral and process chemistry. He joined DSM at the beginning of 2002 as the competence manager for homogeneous catalysis. Dr. Ager is a member of a number of scientific advisory boards. He has over 80 publications including three books. © 2006 by Taylor & Francis Group, LLC Contributors David Ager Michel Bulliard DSM Pharma Chemicals SynKem Raleigh, North Carolina Chenôve Cedex, France and PharQuest LLC Mark Burk Raleigh, North Carolina Diversa Corporation San Diego, California David Allen Stepan Company Dainis Dakternieks Northfield, Illinois Chirogen Pty Ltd Parkville, Victoria, Australia Nelson Barton Diversa Corporation Paul Dalby San Diego, California University College London Department of Biochemical Engineering Colin Bayley London, UK PharQuest LLC Raleigh, North Carolina Ben de Lange DSM Research Jens Beckmann Advanced Synthesis, Catalysis and Chirogen Pty Ltd Development Parkville, Victoria, Australia Geleen, The Netherlands Hans-Ulrich Blaser Johannes de Vries Solvias AG DSM Research Basel, Switzerland Advanced Synthesis, Catalysis and Development Wilhelmus H.J. Boesten Geleen, The Netherlands DSM Research Advanced Synthesis, Catalysis and Development Grace DeSantis Geleen, The Netherlands Diversa Corporation San Diego, California Gary Bond University of Central Lancaster Michael East Centre for Material Science Uquifa Inc. Preston, UK Golf, Illinois Quirinus Broxterman Henk Elsenberg DSM Research DSM Research Advanced Synthesis, Catalysis and Advanced Synthesis, Catalysis and Development Development Geleen, The Netherlands Geleen, The Netherlands © 2006 by Taylor & Francis Group, LLC
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