Chiral sulfamide-catalyzed asymmetric Michael addition of protected 3-hydroxypropanal to β-nitrostyrenes

Abstract Organocatalytic asymmetric Michael addition of 3-(OTBS)-propanal to β-nitrostyrenes catalyzed by chiral sulfamides was investigated. Good d.r. (up to 80:20) and excellent enantioselectivities (up to >99% ee) were achieved. Both the N -[(1 R ,2 R )-2-aminocyclohexyl]- N ’-(phenylmethyl)sulfamide 7b and the novel chiral N -[(1 R ,2 R )-2-aminocyclohexyl]- N ’-[3,5-bis(trifluoromethyl)phenyl]sulfamide 7a were identified as efficient primary amine organocatalysts.