Chapter 2. The Application of DuPHOS Rhodium(I) Catalysts for Commercial Scale Asymmetric Hydrogenation

  1. Dr. Hans-Ulrich Blaser2,
  2. Dr. Elke Schmidt3
  1. Christopher J. Cobley,
  2. Nicholas B. Johnson,
  3. Ian C. Lennon,
  4. Raymond McCague,
  5. James A. Ramsden,
  6. Antonio Zanotti-Gerosa

Published Online: 13 JAN 2004

DOI: 10.1002/3527602151.ch15

Book Title

Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions

Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions

Additional Information

How to Cite

Cobley, C. J., Johnson, N. B., Lennon, I. C., McCague, R., Ramsden, J. A. and Zanotti-Gerosa, A. (2004) The Application of DuPHOS Rhodium(I) Catalysts for Commercial Scale Asymmetric Hydrogenation, in Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions (eds H.-U. Blaser and E. Schmidt), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527602151.ch15

Editor Information

  1. 2

    Solvias AG, P.O. Box, CH-4002 Basel, Switzerland

  2. 3

    Syngenta Crop Protection AG, CH-4058 Basel, Switzerland

Author Information

  1. Dowpharma, Chirotech Technology Ltd, A Subsidiary of The Dow Chemical Company, Unit 321 Cambridge Science Park, Milton Road, Cambridge CB4 0WG, UK

Publication History

  1. Published Online: 13 JAN 2004
  2. Published Print: 6 NOV 2003

ISBN Information

Print ISBN: 9783527306312

Online ISBN: 9783527602155

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CHAPTER TOOLS

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Keywords:

  • DuPHOS rhodium(I) catalysts;
  • asymmetric hydrogenation;
  • fluorophenylalanine;
  • manufacture;
  • synthesis;
  • purity;
  • loading;
  • catalyst;
  • charging

Summary

This chapter contains sections titled:

  • Introduction

  • Large-Scale Manufacture of α-Amino Acids

    • N-Boc-(S)-3-Fluorophenylalanine

    • Experimental for N-t-Butoxycarbonyl-(S)-3-fluorophenylalanine

      • N-Acetyl Dehydro-3-fluorophenylalanine 8 via an Azlactone Intermediate

      • N-Acetyl-3-fluorophenylalanine 9

      • N-BOC-(S)-3-fluorophenylalanine 10

  • Practical and Economic Considerations for Manufacture

    • Manufacture and Choice of Precatalysts

    • Substrate Synthesis, Purity and Catalyst Loading

    • Catalyst Charging

    • Catalyst Removal

  • Conclusions

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