m-CPBA/KOH: an efficient reagent for nucleophilic epoxidation of gem-deactivated olefins.

ABSTRACT

The m-chloroperoxybenzoate anion (generated from m-CPBA and bases such as K(2)CO(3) or KOH) is a highly efficient nucleophilic epoxidating reagent for strongly deactivated olefins containing two electron-withdrawing groups at the same carbon, under mild conditions which affect neither other double bonds nor electrophilic oxidizable centers such as sulfoxides.