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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, Email: Dmacmillcaltech.edu

S. G. Ouellet, J. B. Tuttle, D. W. C. MacMillan, J. Am. Chem. Soc., 2005, 127, 32-33.

DOI: 10.1021/ja043834g (free Supporting Information)


Abstract

The use of a chiral imidazolidinone catalyst has provided a new organocatalytic strategy for the enantioselective reduction of β,β-substituted α,β-unsaturated aldehydes to generate β-stereogenic aldehydes using ethyl Hantzsch ester as the hydrogen source. In addition, an acceleration of E-Z isomerization prior to selective E-olefin reduction allows the use of geometrically impure enals in this operationally simple protocol.

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Key Words

Reduction of Enals, Organocatalysis, Hantzsch Ester


ID: J48-Y2005-2110