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, Georges Dupas.

Journal Name: Letters in Organic Chemistry

Volume 1 , Issue 2 , 2004

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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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Article Details

Year: 2004
Page: [129 - 133]
Pages: 5
DOI: 10.2174/1570178043488365
Price: $65

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