A cooperative N-heterocyclic carbene/chiral phosphate catalysis system for allenolate annulations

Anna Lee, Karl A Scheidt

Research output: Contribution to journalArticlepeer-review

55 Scopus citations

Abstract

The highly enantioselective NHC-catalyzed [3+2] annulation reaction with α,β-alkynals and α-ketoesters has been developed. A new mode of cooperative catalysis involving the combination of a chiral Brønsted acid and a C1-symmetric biaryl saturated-imidazolium precatalyst was required to generate the desired γ-crotonolactones in high yields and levels of enantioselectivity.

Original languageEnglish (US)
Pages (from-to)7594-7598
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number29
DOIs
StatePublished - Jul 14 2014

Keywords

  • N-heterocyclic carbene
  • annulation
  • asymmetric synthesis
  • cooperative catalysis
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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