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

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.