Enantioselective epoxidation of electron-deficient olefins: an organocatalytic approach

Chem Rec. 2011 Feb;11(1):18-39. doi: 10.1002/tcr.201000006. Epub 2010 Nov 30.

Abstract

Versatile synthetic intermediates--α,β-epoxyketones and α,β-epoxyaldehydes--can be obtained through asymmetric organocatalytic epoxidation of α,β-unsaturated ketones and aldehydes. This Review focuses on some recent advances in these epoxidation reactions with respect to scope and limitations with polyamino acids, phase-transfer catalysts (PTCs), amines, and guanidines as chiral organocatalysts. Furthermore, recent results obtained with chiral peroxides are discussed.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Aldehydes / chemistry
  • Alkenes / chemistry*
  • Catalysis
  • Electrons
  • Epoxy Compounds / chemical synthesis
  • Epoxy Compounds / chemistry*
  • Ketones / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Alkenes
  • Epoxy Compounds
  • Ketones