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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

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

Volume 1, Issue 2, 2004

Page: [129 - 133] Pages: 5

DOI: 10.2174/1570178043488365

Price: $65

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


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