Asymmetric Organocatalytic Epoxidation of α,β-Unsaturated Aldehydes with Hydrogen Peroxide

Mauro Marigo, Johan Franzén, Thomas B. Poulsen, Wei Zhuang, and Karl Anker Jørgensen*
Danish National Research Foundation, Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark
J. Am. Chem. Soc., 2005, 127 (19), pp 6964–6965
DOI: 10.1021/ja051808s
Publication Date (Web): April 22, 2005
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.

, kaj@chem.au.dk

Abstract

Abstract Image

The first asymmetric organocatalytic epoxidation of α,β-unsaturated aldehydes is presented. A chiral bisaryl−silyl-protected pyrrolidine acts as a very selective epoxidation organocatalyst using simple oxidation agents, such as hydrogen peroxide and tert-butyl hydroperoxide. The asymmetric epoxidation reactions proceed under environmental friendly reaction condition in, for example, water mixtures of alcohols, and the scope of the reaction is demonstrated by the formation of optically active α,β-epoxy aldehydes in high yields and enantioselectivities >94% ee. Furthermore, the direct synthesis of the sex pheromone from an acaric mite by asymmetric epoxidation of citral is presented.

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History

  • Published In Issue May 18, 2005
  • Received March 22, 2005

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