Ru(salen)-catalyzed asymmetric sulfimidation and subsequent [2,3]sigmatropic rearrangement

(OC)Ru(salen) 1 was found to catalyze sulfimidation of alkyl aryl sulfides in the presence of arylsulfonyl azide with high enantioselectivity, up to 99% ee. When the substrates were allylic sulfides, the resulting sulfimides underwent [2,3]sigmatropic rearrangement to give the corresponding N-allyl toluenesulsulfonamides with greater than 80% ee.