Polymer-Supported Organocatalysts: Asymmetric Reduction of Imines with Trichlorosilane Catalyzed by an Amino Acid-Derived Formamide Anchored to a Polymer†

Andrei V. Malkov, Marek Figlus and Pavel Koovský
Department of Chemistry, WestChem, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, Scotland, U.K.
J. Org. Chem., 2008, 73 (11), pp 3985–3995
DOI: 10.1021/jo800094q
Publication Date (Web): April 30, 2008
Copyright © 2008 American Chemical Society
†

Dedicated to Dr. Vladimír Hanu on the occasion of his 85 birthday.

Abstract

Abstract Image

Asymmetric reduction of ketimines 1a−e with trichlorosilane can be catalyzed by the N-methylvaline-derived Lewis basic formamide anchored to a polymeric support (5a and 5b) with good enantioselectivity (≤82% ee) and low catalyst loading (typically 15 mol %) at room temperature. This protocol represents a considerable simplification of the isolation procedure and is particularly suitable for a parallel synthesis of chiral amines 2a−e. The polymer-supported catalysts retain full activity after a multiple use.

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History

  • Published In Issue June 06, 2008
  • Article ASAPApril 30, 2008
  • Received: January 15, 2008

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