Enantioselective epoxidation of alpha,beta-enones promoted by alpha,alpha-diphenyl-L-prolinol as bifunctional organocatalyst

Org Lett. 2005 Jun 23;7(13):2579-82. doi: 10.1021/ol050694m.

Abstract

[reaction: see text] An operationally simple and mild protocol for the catalytic enantioselective epoxidation of alpha,beta-unsaturated ketones has been estabilished using commercially available alpha,alpha-diphenyl-l-prolinol as bifunctional organocatalyst and tert-butyl hydroperoxide (TBHP) as oxidant. The epoxides have been obtained in good yields and with up to 80% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biphenyl Compounds / chemistry*
  • Catalysis
  • Epoxy Compounds / chemistry*
  • Ketones / chemical synthesis*
  • Ketones / chemistry*
  • Molecular Structure
  • Pyrrolidines / chemistry*
  • Stereoisomerism

Substances

  • Biphenyl Compounds
  • Epoxy Compounds
  • Ketones
  • Pyrrolidines
  • diphenyl
  • prolinol