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

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

Document Type: Review Article

Affiliations: Laboratoire de Chimie Organique Fine et Hétérocyclique, UPRES-A 6014, IRCOF-INSA, B.P 08, F-76131 Mont Saint Aignan, Cedex, France.

Publication date: 2004-04-01

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