Stereoselective synthesis of carbohydrate-derived N-Sulfonyl aziridines

A novel reaction of iodomethyllithium with a variety of sugar-derived N -sulfinyl imines, under very mild conditions, is ­described. N -Sulfonyl aziridines were easily obtained in high yields and in moderate to good stereoselectivities through an addition/­oxidation protocol. A mechanism is proposed that is ­supported by the results of X-ray diffraction studies.