Enantioselective Organocatalytic Hydride Reduction

Stéphane G. Ouellet, Jamison B. Tuttle, and David W. C. MacMillan*
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125
J. Am. Chem. Soc., 2005, 127 (1), pp 32–33
DOI: 10.1021/ja043834g
Publication Date (Web): December 9, 2004
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, Dmacmill@caltech.edu

Abstract

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The first enantioselective organocatalytic hydride reduction has been accomplished. The use of iminium catalysis has provided a new organocatalytic strategy for the enantioselective reduction of β,β-substituted α,β-unsaturated aldehydes to generate β-stereogenic aldehydes. The use of imidazolidinone 2 as the asymmetric catalyst has been found to mediate the transfer of hydrogen to a large class of enal substrates from ethyl Hantzsch ester. The capacity of catalyst 2 to accelerate E−Z isomerization prior to selective E-olefin reduction allows the implementation of geometrically impure enals in this operationally simple protocol.

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History

  • Published In Issue January 12, 2005
  • Received October 10, 2004

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