Synthesis of chiral non-racemic substituted vinyl aziridines

Synthesis of a range of chiral non-racemic vinyl aziridines with varying substitutions on the alkene has been achieved by the reaction of (S_S)-tert-butylphenylsulfinimine with a range of ylides derived by deprotonation of substituted allyltetrahydrothiophenium salts. Yields of the substituted vinyl aziridines range from 0% to 90%, with trans:cis ratios between 1:1 and 0:100 and diastereomeric excesses of up to 99%.