Enantioselective Catalytic Phase Transfer Michael Addition of Methyl 4- Cyano-4-(3,4-Dichlorophenyl)Butanoates on Acrylates

Abstract

Two routes are examined to achieve the synthesis of a glutarimide possessing a quaternary asymmetric centre with good stereocontrol. It appears that the first one, involving enantioselective Michael addition of cyano-4-(3,4-dichlorophenyl)butanoate on allyl acrylate is the most interesting in terms of cleanness of reactions and stereocontrol. The best system involves a quinidine derived catalyst at - 40°C with potassium hydroxide as a base and gave a medium ee (60%). Keywords: phase transfer michael addition, methyl 4- cyano-4-(3,4-dichlorophenyl)butanoates, acrylates, enantioselective Michael addition