Transition-Metal-Free Diastereoselective Epoxidation of Trifluoromethylketones with <i>N</i>-Tosylhydrazones: Access to Tetrasubstituted Trifluoromethylated Oxiranes

Abstract

The first example of the epoxidation reaction of trifluoromethylketones with N-tosylhydrazones under transition-metal free conditions is reported. This epoxidation reaction provided tetrasubstituted trifluoromethylated oxiranes with excellent yields and diastereoselectivities. The salient features of this reaction include readily available starting materials, mild conditions, broad substrate scope, high efficiency, and valuable further applications. Remarkably, this reaction proceeded through an unprecedented nucleophilic addition process, and the ammonium O-anion intermediate was detected and characterized by NMR and HRMS analysis.