Chiral (OC)Ru(salen)-catalyzed tandem sulfimidation and [2,3]sigmatropic rearrangement: asymmetric C-N bond formation

Asymmetric C N bond formation was achieved in a highly enantioselective manner by using (OC)Ru(salen)-catalyzed sulfimidation and the subsequent [2.3]sigmatropic rearrangement: treatment of allyl aryl sulfides with p-toluenesulfonyl azide in the presence of a catalytic amount of (OC)RU(salen) followed by hydrolysis of the resulting N-allyl-N-arylthio toluenesulfon-amides provided N-allyl toluenesulfonamides of high enantiomeric excess. (C) 2002 Elsevier science Ltd. All rights reserved.