Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions, Second Edition

Copyright © 2010 Wiley-VCH Verlag GmbH & Co. KGaA

Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions, Second Edition

Editor(s): Hans-Ulrich Blaser, Hans-Jürgen Federsel

Published Online: 8 JUN 2010

Print ISBN: 9783527324897

Online ISBN: 9783527630639

DOI: 10.1002/9783527630639

About this Book

This second edition of the pioneering work on this hot topic captures the major trends and latest achievements in the art of asymmetric catalysis on an industrial scale. A number of completely new real-life case studies written by the world leaders in their respective areas provide a compact and qualified insight into this developing field. The resulting ready reference and handbook collates first-hand and valuable information within a context where it can be easily found.
The high-quality contributions illustrate the relevant environments and situations, such as time pressure, how the catalytic step fits into the overall synthesis, or competition with other synthetic approaches, as well as the typical problems encountered in the various phases, including finding/developing the catalyst and optimization of the process or choice of equipment. Both successful and unsuccessful approaches to solve these problems are described.

Table of contents

    1. You have free access to this content
      Front Matter (pages i–xxxvii)

  2. Part I: New Processes for Existing Active Compounds (APIs)

    1. Chapter 1

      Some Recent Examples in Developing Biocatalytic Pharmaceutical Processes (pages 1–12)

      Junhua Tao, J. Liu and Z. Chen

    2. Chapter 2

      Enantioselective Hydrogenation: Applications in Process R&D of Pharmaceuticals (pages 13–25)

      Kurt Püntener and Michelangelo Scalone

    3. Chapter 3

      Chiral Lactones by Asymmetric Hydrogenation – A Step Forward in (+)-Biotin Production (pages 27–39)

      Werner Bonrath, Reinhard Karge, Thomas Netscher, Felix Roessler and Felix Spindler

    4. Chapter 4

      Biocatalytic Asymmetric Oxidation for the Production of Bicyclic Proline Peptidomimetics (pages 41–60)

      James J. Lalonde and Jack Liang

    5. Chapter 5

      The Asymmetric Reduction of Heterocyclic Ketones – A Key Step in the Synthesis of Potassium-Competitive Acid Blockers (P-CABs) (pages 61–78)

      Andreas Marc Palmer and Antonio Zanotti-Gerosa

  3. Part II: Processes for Important Buildings Blocks

    1. Chapter 6

      Application of a Multiple-Enzyme System for Chiral Alcohol Production (pages 79–109)

      Junzo Hasegawa, Hirokazu Nanba and Yoshihiko Yasohara

    2. Chapter 7

      Chemoenzymatic Route to the Side-Chain of Rosuvastatin (pages 111–126)

      Robert A. Holt and Christopher D. Reeve

    3. Chapter 8

      Asymmetric Hydrogenation of a 2-Isopropylcinnamic Acid Derivative en Route to the Blood Pressure-Lowering Agent Aliskiren (pages 127–150)

      Jeroen A. F. Boogers, Dirk Sartor, Ulfried Felfer, Martina Kotthaus, Gerhard Steinbauer, Bert Dielemans, Laurent Lefort, André H. M. de Vries and Johannes G. de Vries

    4. Chapter 9

      Asymmetric Phase-Transfer Catalysis for the Production of Non-Proteinogenic α-Amino Acids (pages 151–169)

      Masaya Ikunaka and Keiji Maruoka

    5. Chapter 10

      Development of Efficient Technical Processes for the Production of Enantiopure Amino Alcohols in the Pharmaceutical Industry (pages 171–185)

      Franz Dietrich Klingler

    6. Chapter 11

      The Asymmetric Hydrogenation of Enones – Access to a New L-Menthol Synthesis (pages 187–205)

      Christoph Jäkel and Rocco Paciello

    7. Chapter 12

      Eliminating Barriers in Large-Scale Asymmetric Synthesis (pages 207–218)

      Hideo Shimizu, Noboru Sayo and Takao Saito

    8. Chapter 13

      Catalytic Asymmetric Ring Opening: A Transfer from Academia to Industry (pages 219–229)

      Dirk Spielvogel

    9. Chapter 14

      Asymmetric Baeyer–Villiger Reactions Using Whole-Cell Biocatalysts (pages 231–248)

      Roland Wohlgemuth and John M. Woodley

    10. Chapter 15

      Large-Scale Applications of Hydrolases in Biocatalytic Asymmetric Synthesis (pages 249–264)

      Roland Wohlgemuth

    11. Chapter 16

      Scale-Up Studies in Asymmetric Transfer Hydrogenation (pages 265–290)

      A. John Blacker and Peter Thompson

    12. Chapter 17

      2,2′,5,5′-Tetramethyl-4,4′-bis(diphenylphoshino)-3,3′-bithiophene: A Very Efficient Chiral Ligand for Ru-Catalyzed Asymmetric Hydrogenations on the Multi-Kilograms Scale (pages 291–299)

      Oreste Piccolo

    13. Chapter 18

      The Power of Whole-Cell Reaction: Efficient Production of Hydroxyproline, Sugar Nucleotides, Oligosaccharides, and Dipeptides (pages 301–320)

      Shin-Ichi Hashimoto, Satoshi Koizumi and Akio Ozaki

    14. Chapter 19

      Enantioselective Ketone Hydrogenation: From Research to Pilot Scale with Industrially Viable Ru–(Phosphine–Oxazoline) Complexes (pages 321–329)

      Frédéric Naud, Felix Spindler, Carsten Rueggeberg, Andreas T. Schmidt and Dr. Hans-Ulrich Blaser

  4. Part III: Processes for New Chemical Entities (NCEs)

    1. Chapter 20

      Enabling Asymmetric Hydrogenation for the Design of Efficient Synthesis of Drug Substances (pages 331–376)

      Yongkui Sun, Shane Krska, C. Scott Shultz and David M. Tellers

    2. Chapter 21

      Scale-Up of a Telescoped Enzymatic Hydrolysis Process for an Intermediate in the Synthesis of a Factor Xa Inhibitor (pages 377–396)

      Hans Iding, Beat Wirz, Jean-Michel Adam, Pascal Dott, Wolfgang Haap, Rosa Maria Rodríguez Sarmiento, Thomas Oberhauser, Reinhard Reents, Rolf Fischer and Stephan Lauper

    3. Chapter 22

      An Efficient, Asymmetric Synthesis of Odanacatib, a Selective Inhibitor of Cathepsin K for the Treatment of Osteoporosis, Using an Enzyme-Mediated Dynamic Kinetic Resolution (pages 397–414)

      Matthew D. Truppo

    4. Chapter 23

      Biocatalytic Routes to the GPIIb/IIIa Antagonist Lotrafiban, SB 214857 (pages 415–437)

      Andy Wells

    5. Chapter 24

      Discovery and Development of a Catalytic Asymmetric Conjugate Addition of Ketoesters to Nitroalkenes and Its Use in the Large-Scale Preparation of ABT-546 (pages 439–455)

      David M. Barnes

    6. Chapter 25

      The Kagan Oxidation – Industrial-Scale Asymmetric Sulfoxidations in the Synthesis of Two Related NK1/NK2 Antagonists (pages 457–471)

      David R. J. Hose, Bharti Patel, Sharon A. Bowden and Jonathan D. Moseley

    7. Chapter 26

      Large-Scale Application of Asymmetric Phase-Transfer Catalysis for Amino Acid Synthesis (pages 473–484)

      Daniel E. Patterson, Shiping Xie, Lynda A. Jones, Martin H. Osterhout, Christopher G. Henry and Thomas D. Roper

    8. Chapter 27

      Application of Phase-Transfer Catalysis in the Organocatalytic Asymmetric Synthesis of an Estrogen Receptor Beta-Selective Agonist (pages 485–497)

      Jeremy P. Scott

    9. Chapter 28

      Asymmetric Synthesis of HCV and HPV Drug Candidates on Scale: The Choice between Enantioselective and Diastereoselective Syntheses (pages 499–522)

      Jeremy D. Cobb, Bob E. Cooley, Roy C. Flanagan, Mary M. Jackson, Lynda A. Jones, Richard T. Matsuoka, Alan Millar, Daniel E. Patterson, Matthew J. Sharp, Jennifer F. Toczko, Shiping Xie and Xiaoming Zhou

    1. You have free access to this content
      Index (pages 523–542)

SEARCH