Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions

Copyright © 2004 Wiley-VCH Verlag GmbH & Co. KGaA

Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions

Editor(s): Hans-Ulrich Blaser, Elke Schmidt

Published Online: 13 JAN 2004

Print ISBN: 9783527306312

Online ISBN: 9783527602155

DOI: 10.1002/3527602151

About this Book

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Edited by two of the experts in the field, the central aim is to show organic chemists working in process development that enantioselective catalysis is suitable for the large-scale production of enantioenriched intermediates. In so doing, it is equally a source of information and inspiration for academic research, and, with its contribution by Noble prizewinner W. S. Knowles, will also heighten the status of industrial catalyst specialists working in the exciting field of enantioselective catalysis.

Some 25 contributions from top industrial researchers around the world present case studies on the development of the widest possible range of large-scale enantioselective processes, featuring stereoselective production processes of fine-chemicals, agrochemicals and pharmaceuticals. Clearly structured according to the nature of the task, this handbook adopts a problem-driven approach such that readers can easily find how colleagues have dealt with a similar situation.

Table of contents

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      Front Matter (pages i–xxvi)

    1. Introduction (pages 1–19)

      Dr. Hans-Ulrich Blaser and Dr. Elke Schmidt

  3. Part I: New Processes for Existing Active Compounds

    1. Chapter 1

      Asymmetric Hydrogenations – The Monsanto L-Dopa Process (pages 21–38)

      William S. Knowles

    2. Chapter 2

      The Other L-Dopa Process (pages 39–53)

      Rüdiger Selke

    3. Chapter 3

      The Chiral Switch of Metolachlor: The Development of a Large-Scale Enantioselective Catalytic Process (pages 55–70)

      Dr. Hans-Ulrich Blaser, Reinhard Hanreich, Hans-Dieter Schneider, Felix Spindler and Beat Steinacher

    4. Chapter 4

      Enantioselective Hydrogenation: Towards a Large-Scale Total Synthesis of (R,R,R)-α-Tocopherol (pages 71–89)

      Thomas Netscher, Michelangelo Scalone and Rudolf Schmid

    5. Chapter 5

      Comparison of Four Technical Syntheses of Ethyl (R)-2-Hydroxy-4-Phenylbutyrate (pages 91–103)

      Dr. Hans-Ulrich Blaser, Marco Eissen, Pierre F. Fauquex, Konrad Hungerbühler, Dr. Elke Schmidt, Gottfried Sedelmeier and Martin Studer

    6. Chapter 6

      Biocatalytic Approaches for the Large-Scale Production of Asymmetric Synthons (pages 105–115)

      Nicholas M. Shaw, Karen T. Robins and Andreas Kiener

    7. Chapter 7

      7-Aminocephalosporanic Acid – Chemical versus Enzymatic Production Process (pages 117–130)

      Thomas Bayer

    8. Chapter 8

      Methods for the Enantioselective Biocatalytic Production of L-Amino Acids on an Industrial Scale (pages 131–147)

      Harald Gröger and Karlheinz Drauz

  4. Part II: New Catalysts for Existing Active Compounds

    1. Chapter 1

      The Large-Scale Biocatalytic Synthesis of Enantiopure Cyanohydrins (pages 149–164)

      Peter Poechlauer, Wolfgang Skranc and Marcel Wubbolts

    2. Chapter 2

      Industrialization Studies of the Jacobsen Hydrolytic Kinetic Resolution of Epichlorohydrin (pages 165–199)

      Larbi Aouni, Karl E. Hemberger, Serge Jasmin, Hocine Kabir, Jay F. Larrow, Isidore Le-Fur, Philippe Morel and Thierry Schlama

    3. Chapter 3

      Scale-Up Studies in Asymmetric Transfer Hydrogenation (pages 201–216)

      John Blacker and Juliette Martin

    4. Chapter 4

      Practical Applications of Biocatalysis for the Manufacture of Chiral Alcohols Such as (R)-1,3-Butanediol by Stereospecific Oxidoreduction (pages 217–231)

      Akinobu Matsuyama and Hiroaki Yamamoto

    5. Chapter 5

      Production of Chiral C3 and C4 Units via Microbial Resolution of 2,3-Dichloro-1-propanol, 3-Chloro-1,2-propanediol and Related Halohydrins (pages 233–256)

      Naoya Kasai and Toshio Suzuki

  5. Part III: Adaptation of Existing Catalysts for Important Building Blocks

    1. Chapter 1

      Synthesis of Unnatural Amino Acids (pages 258–268)

      David J. Ager and Scott A. Laneman

    2. Chapter 2

      The Application of DuPHOS Rhodium(I) Catalysts for Commercial Scale Asymmetric Hydrogenation (pages 269–282)

      Christopher J. Cobley, Nicholas B. Johnson, Ian C. Lennon, Raymond McCague, James A. Ramsden and Antonio Zanotti-Gerosa

    3. Chapter 3

      Liberties and Constraints in the Development of Asymmetric Hydrogenations on a Technical Scale (pages 283–308)

      John F. McCarrity, Walter Brieden, Rudolf Fuchs, Hans-Peter Mettler, Beat Schmidt and Oleg Werbitzky

    4. Chapter 4

      Large-Scale Applications of Biocatalysis in the Asymmetric Synthesis of Laboratory Chemicals (pages 309–319)

      Roland Wohlgemuth

  6. Part IV: Processes for New Chemical Entities (NCE)

    1. Chapter 1

      Development of an Efficient Synthesis of Chiral 2-Hydroxy Acids (pages 321–334)

      Junhua Tao and Kevin McGee

    2. Chapter 2

      Factors Influencing the Application of Literature Methods toward the Preparation of a Chiral trans-Cyclopropane Carboxylic Acid Intermediate during Development of a Melatonin Agonist (pages 335–348)

      Ambarish K. Singh, J. Siva Prasad and Edward J. Delaney

    3. Chapter 3

      Hetero Diels-Alder-Biocatalysis Approach for the Synthesis of (S)-3-[2-{(Methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol Methanesulfonate: Successful Application of an Enzyme Resolution Process (pages 349–363)

      Jean-Claude Caille, Jim Lalonde, Yiming Yao and C. K. Govindan

    4. Chapter 4

      Multi-Kilo Resolution of XU305, a Key Intermediate to the Platelet Glycoprotein IIb/IIIa Receptor Antagonist Roxifiban via Kinetic and Dynamic Enzymatic Resolution (pages 365–384)

      Jaan A. Pesti and Luigi Anzalone

    5. Chapter 5

      Protease-Catalyzed Preparation of (S)-2-[(tert-Butylsulfonyl)-methyl]-hydrocinnamic Acid for Renin Inhibitor RO0425892 (pages 385–398)

      Beat Wirz, Stephan Doswald, Ernst Kupfer, Wolfgang Wostl, Thomas Weisbrod and Heinrich Estermann

    6. Chapter 6

      Protease-Catalyzed Preparation of Chiral 2-Isobutyl Succinic Acid Derivatives for Collagenase Inhibitor RO0319790 (pages 399–411)

      Beat Wirz, Milan Soukup, Thomas Weisbrod, Florian Stäbler and Rolf Birk

    7. Chapter 7

      An Innovative Asymmetric Sulfide Oxidation: The Process Development History behind the New Antiulcer Agent Esomeprazole (pages 413–436)

      Hans-Jürgen Federsel and Magnus Larsson

    8. Chapter 8

      Development of a Biocatalytic Process for the Resolution of (R)- and (S)-Ethyl 3-amino-4-pentynoate Isomers Using Enzyme Penicillin G Amidohydrolase (pages 437–449)

      Ravindra S. Topgi

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      Subject Index (pages 451–454)

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