Catalytic asymmetric synthesis of 2,2-disubstituted terminal epoxides via dimethyloxosulfonium methylide addition to ketones

J Am Chem Soc. 2008 Aug 6;130(31):10078-9. doi: 10.1021/ja803864p. Epub 2008 Jul 10.

Abstract

Catalytic asymmetric Corey-Chaykovsky epoxidation of ketones with dimethyloxosulfonium methylide 2 using an LLB 1a + Ar3P O complex proceeded smoothly at room temperature, and 2,2-disubstituted terminal epoxides were obtained in high enantioselectivity (91-97%) and yield (>88-99%) from a broad range of methyl ketones with 1-5 mol % catalyst loading. The use of achiral additive Ar3P O 5i was important to achieve high enantioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Epoxy Compounds / chemical synthesis*
  • Ketones / chemistry*
  • Organophosphorus Compounds
  • Sulfonium Compounds / chemistry*

Substances

  • Epoxy Compounds
  • Ketones
  • Organophosphorus Compounds
  • Sulfonium Compounds
  • dimethyloxosulfonium methylide