title: Selective Epoxidation of Olefins by Perfluoro-cis-2,3-dialkyloxaziridines(1).
abstract: 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.
authors.affiliation: H. L. Hunter Chemistry Laboratory, Clemson University, Clemson, South Carolina, 29634-1905, CNR-Centro Studio Sostanze Organiche Naturali, Politecnico, 7 via Mancinelli, I-20131 Milano, Italy, and Dipartimento Chimica Farmaceutica, Università, 12 via Taramelli, I-27100 Pavia, Italy.
authors.forename: Alberto
authors.initials: A
authors.lastname: Arnone
authors.forename: Darryl D.
authors.initials: DD
authors.lastname: DesMarteau
authors.forename: Barbara
authors.initials: B
authors.lastname: Novo
authors.forename: Viacheslav A.
authors.initials: VA
authors.lastname: Petrov
authors.forename: Massimo
authors.initials: M
authors.lastname: Pregnolato
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Resnati