Catalytic Enantioselective Reaction of 2H-Azirines with Thiols Using Cinchona Alkaloid Sulfonamide Catalysts.

The first catalytic enantioselective reaction of 2H-azirines with thiols has been developed. The obtained aziridines can be converted to optically active oxazolines, aziridylamides, or α-sulfonyl esters. Transformation of these optically active aziridines showed that 2H-azirines act as β,β-dicarbocationic amine synthons.