Synthesis of N-tosylaziridines from substituted alkenes via zirconooxaziridine catalysis

Herein we report the zirconooxaziridine promoted aziridination of alkenes using chloramine T as the quantitative source of N. The reaction works with high yields, diastereoselectivities and stereospecificity for a wide variety of substituted alkenes. A potential mechanism involving the formation of a zirconooxaziridine complex as the active catalyst has been proposed and initial mechanistic data would indicate that a highly associative mechanism is the predominant pathway for this transformation.