Asymmetric synthesis of 4H-1,3-oxazines: enantioselective reductive cyclization of N-acylated beta-amino enones with trichlorosilane catalyzed by chiral Lewis bases

Chem Commun (Camb). 2009 Jun 28:(24):3585-7. doi: 10.1039/b905102c. Epub 2009 May 11.

Abstract

N-Acylated beta-amino enones reductively cyclize by treatment with trichlorosilane and a chiral Lewis base catalyst to afford optically active 4H-1,3-oxazines, which can be transformed to other chiral compounds without racemization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Amines / chemistry*
  • Catalysis
  • Cyclization
  • Molecular Structure
  • Oxazines / chemical synthesis*
  • Oxazines / chemistry
  • Oxidation-Reduction
  • Silanes / chemistry*
  • Stereoisomerism

Substances

  • Amines
  • Oxazines
  • Silanes
  • trichlorosilane