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

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

Volume: 1 Issue: 2

Author(s): Patrice Cann, Vincent Levacher, Jean Bourguignon and Georges Dupas

Affiliation:

Keywords: phase transfer michael addition, methyl 4- cyano-4-(3,4-dichlorophenyl)butanoates, acrylates, enantioselective Michael addition

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%).

Cite this article as:

Cann Patrice, Levacher Vincent, Bourguignon Jean and Dupas Georges, Enantioselective Catalytic Phase Transfer Michael Addition of Methyl 4- Cyano-4-(3,4-Dichlorophenyl)Butanoates on Acrylates, Letters in Organic Chemistry 2004; 1 (2) . https://dx.doi.org/10.2174/1570178043488365