Selective epoxidation of olefins by perfluoro-cis-2,3-dialkyloxaziridines

Alkyl-substituted olefins are epoxidized by perfluoro-cis-2,3-dialkyloxaziridines under particularly mild conditions. Electron deficient substrates (e.g, alpha,beta-enones) can also be epoxidized, and the more electron poor the double bond is, the more severe the reactions conditions become. The epoxidation is chemoselective (secondary alcohols and their ethers do not interfere), site selective (the monoepoxide of a diene can be obtained), and stereoselective (cis-alkenes afford cis-epoxides). Various complex and polyfunctional substrates of natural origin (monoterpenes, sesquiterpenes, steroids) have been transformed effectively.