Selective Synthesis of <i>cis</i>- and <i>trans</i>-2-(Methyl/phenyl)-3-(trifluoromethyl)aziridines and Their Regio- and Stereospecific Ring Opening

Abstract

A convenient and stereoselective approach toward <i>cis</i>- and <i>trans</i>-1-alkyl-2-(methyl/phenyl)-3-(tri­fluoro­methyl)­aziridines was developed starting from the corresponding α,α,α-trifluoroketones via imination, α-chlorination, and hydride-induced ring closure. The reactivity of these newly synthesized nonactivated α-CF₃-aziridines was evaluated by applying <i>N</i>-protonation or <i>N</i>-alkylation to effect regio- and stereospecific aziridine ring opening by oxygen, halogen, sulfur, and nitrogen nucleophiles. Furthermore, nonactivated α-CF₃-aziridines were easily transformed into their activated analogues by replacing the <i>N</i>-benzyl protecting group with a <i>N</i>-tosyl group, rendering these α-CF₃-aziridines much more susceptible to nucleophilic ring opening