Chapter 11. Chiral Pentacoordinated Manganese Complexes As Biomimetic Catalysts for Asymmetric Epoxidations with Hydrogen Peroxide

  1. Waldemar Adam
  1. Albrecht Berkessel,
  2. Thomas Schwenkreis,
  3. Matthias Frauen-Kron,
  4. Adrian Steinmetz,
  5. Norbert Schätz and
  6. Jochen Prox

Published Online: 30 JUN 2005

DOI: 10.1002/3527600396.ch24

Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer

Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer

How to Cite

Berkessel, A., Schwenkreis, T., Frauen-Kron, M., Steinmetz, A., Schätz, N. and Prox, J. (2000) Chiral Pentacoordinated Manganese Complexes As Biomimetic Catalysts for Asymmetric Epoxidations with Hydrogen Peroxide, in Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer (ed W. Adam), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527600396.ch24

Editor Information

  1. Institut für Organische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany

Author Information

  1. Institut für Organische Chemie, Universität zu Köln, Greinstrasse 4, D-50939 Köln, Germany

Publication History

  1. Published Online: 30 JUN 2005
  2. Published Print: 11 SEP 2000

ISBN Information

Print ISBN: 9783527271504

Online ISBN: 9783527600397

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Keywords:

  • biomimetic catalysts;
  • pentacoordinated manganese complexes;
  • asymmetric epoxidation;
  • hydrogen peroxide;
  • manganese chelates;
  • asymmetric induction

Summary

This chapter contains sections titled:

  • Introduction

  • Results

    • Synthesis and Catalytic Performance of Pentacoordinated Peroxidase Models

      • Synthesis of the Ligands and Manganese Complexes

      • X-Ray Crystal Structures

      • Asymmetric Epoxidation with Hydrogen Peroxide Catalyzed by the Enantiomerically Pure Manganese Chelates 7a,c,h,i

      • Asymmetric Epoxidation Catalyzed by the Manganese Chelate 7a Using Terminal Oxidants Other than Hydrogen Peroxide

      • Further Variations on the Catalyst Structure: Epoxidation of 1,2-Dihydronaphthalene 8 Catalyzed by the Manganese Chelates rac-7b-e and rac-7g

    • Manganese Chelates Derived from Amino Acids

  • Discussion

    • Pentadentate Manganese(III) Complexes of the Dihydrosalen Type as Peroxidase Models and as New Epoxidation Catalysts

    • On the Mechanism of Asymmetric Induction

    • Stability of the Catalysts

  • Conclusion

    • Acknowledgements

  • References