Aziridination of N-sulfonylimines with a stabilized sulfonium ylide: simple preparation of N-sulfonyl-2-[(E)-2-(alkoxycarbonyl)ethenyl]-3-arylaziridines

Abstract

N-Sulfonyl-2-[(E)-2-(alkoxycarbonyl)ethenyl]-3-arylaziridines 1 are efficiently prepared either by the reaction of N-sulfonylimines 2 with 3-(alkoxycarbonyl)allyldimethylsulfonium bromide 3 in the presence of potassium carbonate in acetonitrile at room temperature or by the reaction of compounds 2 with preformed dimethylsulfonium 3-(alkoxycarbonyl)allylides 4 at –78 °C in moderate to good yields. The cis/trans value of the product ranged from 1/1 to 8/1.