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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%).

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: April 1, 2004

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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
    The journal is essential reading for all organic chemists both in academia and industry.

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