Organocatalytic transfer hydrogenation of cyclic enones

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

Research output: Contribution to journalArticle

189 Scopus citations

Abstract

The first enantioselective organocatalytic transfer hydrogenation of cyclic enones 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 cycloalkenones, to generate β-stereogenic cyclic ketones. The use of imidazolidinone 4 as the asymmetric catalyst has been found to mediate the hydrogenation of a large class of enone substrates with tert-butyl Hantzsch ester serving as an inexpensive source of hydrogen. The capacity of catalyst 4 to enable enantioselective transfer hydrogenation of cycloalkenones has been extended to five-, six-, and seven-membered ring systems. The sense of asymmetric induction is in complete accord with the stereochemical model first reported in conjunction with the use of catalyst 4 for enantioselective ketone Diels-Alder reactions.

Original languageEnglish (US)
Pages (from-to)12662-12663
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number39
DOIs
StatePublished - Oct 4 2006

All Science Journal Classification (ASJC) codes

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

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