One pot synthesis of homochiral aziridines and aminoalcohols from homochiral 1,2-cyclic sulfates

Abstract Preparations of homochiral N -substituted aziridines and aminoalcohols from 1,2-cyclic sulfates are reported. Primary amines react with cyclic sulfates to give β-aminosulfates which can be converted either to aziridines or to aminoalcohols by treatment with base or aqueous acid, respectively. Reaction of cyclic sulfates with azide followed by LiAlH 4 reduction/cyclization yields N -unsubstituted aziridines.