Aza-pinacol rearrangement: acid-catalyzed rearrangement of aziridines to imines

Abstract

A series of di-, tri-, and tetra-substituted N-tosylaziridines [N-(toluene-p-sulfonyl)aziridines] 1, prepared by aziridination of the corresponding alkenes with N-[(tolyl-p-sulfonyl)- imino]phenyliodinane (TsN=IPh), was found to undergo a BF₃-catalyzed rearrangement (aza-pinacol rearrangement) under mild conditions to give the corresponding N-tosylimines 2 generally in satisfactory yields.