Organocatalytic asymmetric Michael addition of oxindoles to nitroolefins for the synthesis of 2,2-disubstituted oxindoles bearing adjacent quaternary and tertiary stereocenters.

A bifunctional thiourea-catalyzed Michael addition of activated indolin-3-ones to nitroolefins has been developed. The synthetically useful 2,2-disubstituted indolin-3-one derivatives with vicinal chiral quaternary-tertiary stereocenters were obtained in high yields with excellent stereoselectivities. The adduct can be readily transformed into a structurally interesting heterocyclic architecture by means of further synthetic elaboration.