Adapting Bower's Intramolecular Aziridination Reaction Allows for a Metal-Free Synthesis of N-H Aziridines

Abstract

Inspired by Bower's intramolecular aziridination reaction, we have developed an intermolecular protocol for the preparation of N-H aziridines from olefins. Our reaction is operationally simple and involves stirring substrate with commercial N-Boc-O-tosylhydroxylamine and trifluoroacetic acid in 2,2,2-trifluoroethanol. The reaction is stereospecific, scalable, and does not utilize expensive transition metals. The substrate scope is broad, and the functional group tolerance is impressive.