Tetrahedron Letters

Epoxidation of olefins by β-bromoalkoxydimethylsulfonium ylides

G Majetich, J Shimkus, Y Li

Index: Majetich, George; Shimkus, Joel; Li, Yang Tetrahedron Letters, 2010 , vol. 51, # 52 p. 6830 - 6834

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Citation Number: 8

Abstract

Olefins can be converted to their respective epoxides in a one-pot procedure by dissolving the olefin in anhydrous DMSO, adding NBS to the reaction mixture to generate a β- bromoalkoxydimethylsulfonium ylide, and then adding DBU to the reaction mixture. A large variety of alkenes were successfully epoxidized with yields largely dependent on the structure of the alkene. Most importantly, the facial selectivity of this one-pot process is the ...