Catalytic enantioselective epoxidation of tertiary allylic and homoallylic alcohols

J Am Chem Soc. 2013 Mar 6;135(9):3411-3. doi: 10.1021/ja401182a. Epub 2013 Feb 19.

Abstract

An efficient and versatile method for the enantioselective epoxidation of both tertiary allylic and homoallylic alcohols catalyzed by Hf(IV)-bishydroxamic acid (BHA) complexes is described. Asymmetric epoxidation, kinetic resolution, and desymmetrization have been developed, demonstrating the flexible nature of the Hf(IV)-BHA system. This is the first report in which these substrates were obtained with enantioselectivities of up to 99%.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Epoxy Compounds / chemical synthesis*
  • Epoxy Compounds / chemistry
  • Molecular Structure
  • Propanols / chemistry*
  • Stereoisomerism

Substances

  • Epoxy Compounds
  • Propanols
  • allyl alcohol