Highly enantioselective epoxidation of alpha, beta-unsaturated esters by chiral dioxirane

J Am Chem Soc. 2002 Jul 31;124(30):8792-3. doi: 10.1021/ja020478y.

Abstract

This paper describes a highly enantioselective epoxidation of alpha,beta-unsaturated esters using the fructose-derived ketone 2 as catalyst and Oxone as oxidant. High ee's have been obtained for a number of trans and trisubstituted substrates (82-98% ee). The results described show that it is feasible for dioxiranes to effectively epoxidize electron-deficient olefins with high ee's.

Publication types

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

MeSH terms

  • Cinnamates / chemistry*
  • Epoxy Compounds / chemical synthesis*
  • Epoxy Compounds / chemistry*
  • Ketones / chemistry
  • Stereoisomerism
  • Sulfuric Acids / chemistry

Substances

  • Cinnamates
  • Epoxy Compounds
  • Ketones
  • Sulfuric Acids
  • dioxirane
  • potassium peroxymonosulfuric acid