Highly enantioselective organocatalytic carbonyl-ene reaction with strongly acidic, chiral Brønsted acids as efficient catalysts

Magnus Rueping*, Thomas Theissmann, Alexander Kuenkel, René M. Koenigs

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

165 Scopus citations

Abstract

(Chemical Equation Presented) You can count on the counterion in ion-pair intermediates to induce high levels of asymmetry in the title reaction. The efficient transformation proceeds under mild reaction conditions in the presence of an air-stable N-triflylphosphoramide in a low catalyst loading of just 1 mol% to give substituted α-hydroxyesters in good yields and with excellent ee values (see scheme; R = aryl).

Original languageEnglish (US)
Pages (from-to)6798-6801
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number36
DOIs
StatePublished - Aug 25 2008

Keywords

  • Asymmetric catalysis
  • Brønsted acids
  • Carbonyl-ene reaction
  • Ion pairs
  • Organocatalysis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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