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
Letters in Organic Chemistry
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%).
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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
DOI https://dx.doi.org/10.2174/1570178043488365 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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