Chiral Sulfamides as Bifunctional Catalysts in Conjugate Addition Reactions

Significance

The authors report the synthesis of chiral sulfamides and their use as bifunctional catalysts in the conjugate addition of aldehydes to ­nitroolefines. The sulfamide primary amine catalyst 1 turned out to give the best results regarding enantioselectivity and yield. The use of Brønsted-basic additives had a beneficial effect on the reaction rate, presumably accelerating steps II and III of the catalytic cycle. The desired products were obtained in good yields and excellent enantio­selectivities.