Chapter 5. Preparation of Optically Active Hydroperoxides and Their Use for Stereoselective Oxygen Transfer

  1. Waldemar Adam
  1. Hans-Jürgen Hamann,
  2. Eugen Höft and
  3. Jürgen Liebscher

Published Online: 30 JUN 2005

DOI: 10.1002/3527600396.ch18

Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer

Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer

How to Cite

Hamann, H.-J., Höft, E. and Liebscher, J. (2000) Preparation of Optically Active Hydroperoxides and Their Use for Stereoselective Oxygen Transfer, 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.ch18

Editor Information

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

Author Information

  1. Institut für Chemie, Humboldt-Universität zu Berlin, Hessische Strasse 1– 2, D-10115 Berlin, 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:

  • optically active hydroperoxides;
  • kinetic resolutions;
  • Sharpless epoxidation;
  • hydroperoxides;
  • enzymatic resolutions;
  • pinane hydroperoxides;
  • azido hydroperoxides;
  • stereoselective oxygen transfer

Summary

This chapter contains sections titled:

  • Introduction

  • Generation of Optically Active Hydroperoxides

    • Kinetic Resolutions

      • Kinetic Resolution via Sharpless Epoxidation

      • Kinetic Resolution by Decomposition of Hydroperoxides

      • Enzymatic Resolutions of Hydroperoxides

    • HPLC on Chiral Stationary Phases

    • Optically Active Hydroperoxides from the “Chiral Pool”

      • Pinane Hydroperoxides

      • Azido hydroperoxides

      • Hydroperoxides Derived from Sugars

  • Use of Optically Active Hydroperoxides for Stereoselective Oxygen Transfer

    • Epoxidation

    • Oxidation of Sulfides

  • References