N-Heterocyclic Carbene-Catalyzed δ-Carbon LUMO Activation of Unsaturated Aldehydes

J Am Chem Soc. 2015 May 6;137(17):5658-61. doi: 10.1021/jacs.5b02219. Epub 2015 Apr 28.

Abstract

An N-heterocyclic carbene (NHC) catalyzed domino reaction triggered by a δ-LUMO activation of α,β-γ,δ-diunsaturated enal has been developed for the formal [4 + 2] construction of multisubstituted arenes and 3-ylidenephthalide. These two products, formed in a highly chemo- and regioselective manner, were obtained via different catalytic pathways due to a simple change of the substrate. The activation of the remote δ-carbon of unsaturated aldehydes expands the synthetic potentials of NHC organocatalysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Benzene Derivatives / chemical synthesis
  • Benzene Derivatives / chemistry
  • Benzofurans / chemical synthesis
  • Benzofurans / chemistry
  • Carbon / chemistry*
  • Catalysis
  • Cyclization
  • Heterocyclic Compounds / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Aldehydes
  • Benzene Derivatives
  • Benzofurans
  • Heterocyclic Compounds
  • carbene
  • Carbon
  • phthalide
  • Methane