Enantioselective N-heterocyclic carbene catalysis by the umpolung of α,β-unsaturated ketones

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Abstract

N-Heterocyclic carbene-catalyzed formation of β-anionic intermediates from enones has been employed in the enantioselective synthesis of 2-aryl propionates. The reaction was achievable using a homochiral 4-MeOC6H4 morpholinone catalyst allowing the first example of enantioselective catalysis by umpolung of α,β-unsaturated ketones. The reaction is high yielding, and shows robustness with reasonable generality. A mechanism is proposed in which the enantiodetermining protonation is achieved using either hexafluoroisopropanol or the formed naphthol product.

Original languageEnglish
Pages (from-to)3135-3139
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number9
DOIs
Publication statusPublished - 24 Feb 2016

Keywords

  • 1,4-addition
  • 2-aryl propionates
  • enantioselective catalysis
  • N-heterocyclic carbenes
  • β-azolium ylides

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