Designing N-heterocyclic carbenes: simultaneous enhancement of reactivity and enantioselectivity in the asymmetric hydroacylation of cyclopropenes

Angew Chem Int Ed Engl. 2011 Dec 23;50(52):12626-30. doi: 10.1002/anie.201106155. Epub 2011 Nov 4.

Abstract

Faster, higher, stronger! The N-heterocyclic carbene (NHC) catalyzed diastereo- and enantioselective hydroacylation of cyclopropenes affords structurally valuable acylcyclopropanes. A new family of electron-rich, 2,6-dimethoxyphenyl-substituted NHCs induces excellent reactivity and enantioselectivity. Preliminary kinetic studies unambiguously demonstrated the superiority of this family of catalysts over known NHCs in this challenging transformation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Crystallography, X-Ray
  • Cyclopropanes / chemical synthesis*
  • Cyclopropanes / chemistry
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Methane / analogs & derivatives*
  • Methane / chemical synthesis
  • Methane / chemistry
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism

Substances

  • Cyclopropanes
  • Heterocyclic Compounds
  • carbene
  • cyclopropene
  • Methane