Highly enantioselective organocatalytic formation of a quaternary carbon center via chiral Brønsted acid catalyzed self-coupling of enamides

Chem Commun (Camb). 2008 Oct 14:(38):4637-9. doi: 10.1039/b804477e. Epub 2008 Aug 5.

Abstract

The enantioselective BINOL-phosphate catalyzed formation of a quaternary carbon center, bearing a N-atom has been achieved through the self-coupling reaction of enamides; the corresponding products have been isolated in up to >99% ee and their application for the synthesis of versatile synthetic building blocks-beta-aminoketones-has been demonstrated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids / chemistry*
  • Amides / chemistry*
  • Carbon / chemistry*
  • Catalysis
  • Naphthols / chemistry*
  • Phosphates / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Acids
  • Amides
  • BINOL, naphthol
  • Naphthols
  • Phosphates
  • Carbon