Highly selective ylide-initiated Michael addition/cyclization reaction for synthesis of cyclohexadiene epoxide and vinylcyclopropane derivatives

J Org Chem. 2010 May 21;75(10):3454-7. doi: 10.1021/jo100306z.

Abstract

On the basis of the reactions of camphor-derived sulfur ylide with alpha,beta-unsaturated ketone, highly efficient and selective synthesis of optically active cyclohexadiene epoxides and vinylcyclopropanes with excellent diastereoselectivities, moderate to high enantioselectivities, and yields has been achieved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Cyclohexenes / chemical synthesis*
  • Cyclohexenes / chemistry
  • Cyclopropanes / chemical synthesis*
  • Cyclopropanes / chemistry
  • Epoxy Compounds / chemical synthesis*
  • Epoxy Compounds / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Vinyl Compounds / chemical synthesis*
  • Vinyl Compounds / chemistry

Substances

  • Cyclohexenes
  • Cyclopropanes
  • Epoxy Compounds
  • Vinyl Compounds