Ring-Opening of Aziridines by Pendant Sulfamates Allows for Regioselective and Stereospecific Preparations of Vicinal Diamines

The ring-opening of aziridines by pendant sulfamates is a viable strategy for the rapid preparation of vicinal diamines. Our reaction is compatible with both di-substituted cis and trans aziridines; unsubstituted, N-alkyl, and N-aryl sulfamates engage effectively. In all cases examined, the cyclization reaction is perfectly regioselective and stereospecific. Once activated, the product oxathiazinane heterocycles can be ring-opened with a diverse range of nucleophiles.