Highly diastereoselective and enantioselective direct Michael addition of phthalide derivatives to nitroolefins

Abstract

The first asymmetric Michael addition of 3-substituted phthalides to nitroolefins promoted by amino acid-incorporating multifunctional catalysts has been developed. The reported method led to the synthesis of 3,3-disubstituted phthalide derivatives in high yields, and in a highly diastereoselective and enantioselective manner. Facile synthesis of a chiral bicyclic lactam has also been demonstrated. © 2013 The Royal Society of Chemistry.