Enantioselective organocatalytic hydride reduction

Stéphane G. Ouellet, Jamison B. Tuttle, David W.C. MacMillan

Research output: Contribution to journalArticle

399 Scopus citations

Abstract

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 αβ-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.

Original languageEnglish (US)
Pages (from-to)32-33
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number1
DOIs
StatePublished - Jan 12 2005
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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