Highly enantio- and diastereoselective Michael addition of cyclohexanone to nitroolefins catalyzed by a chiral glucose-based bifunctional secondary amine-thiourea catalyst

A novel bifunctional thiourea bearing a saccharide-scaffold and a secondary amino group was synthesized, and was proven to be an effective organocatalyst for the asymmetric Michael reaction of cyclohexanone to both aryl and alkyl nitroolefins. The corresponding adducts were obtained with excellent diastereo- (up to >99/1 dr) and enantioselectivities (up to 97% ee).