A facile,one-pot synthesis of Ephedra-based aziridines

A series of enantiomerically and diastereomerically enriched N-sulfonylaziridines have been prepared by a single-pot process from (1R,2S)- and (1S,2R)-norephedrine and (1S,2S)-pseudonorephedrine. The cyclization process involved N-sulfonylation of the Ephedra alkaloid followed by O-sulfonylation with methanesulfonyl chloride. The bis(sulfonyl)Ephedra derivatives were treated with either hydrazine or sodium hydroxide to afford the N-sulfonylaziridines.