Selective Epoxidation of Olefins by Perfluoro-cis-2,3-dialkyloxaziridines(1).
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.
Arnone
Alberto
A
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.
DesMarteau
Darryl D.
DD
Novo
Barbara
B
Petrov
Viacheslav A.
VA
Pregnolato
Massimo
M
Resnati
Giuseppe
G