Copper-Catalyzed Michael Reactions Research Articles

Catalytic Michael Reactions of Ketoesters with a Camphor-Derived Acrylate Equivalent: Stereoselective Access to All-Carbon Quaternary Centers

A camphor-based alpha'-hydroxy enone reagent acts as a chiral acrylate equivalent in copper-catalyzed Michael reactions of beta-keto esters and affords products that possess all-carbon quaternary stereocenters of high enantiomeric purity.

A Poly(ethylene glycol)-Supported Chiral Auxiliary for Asymmetric Michael Reaction

Poly(ethylene glycol)-supported l-valine-derived auxiliary 1 was prepared from poly(ethylene glycol) dimesylate in four steps. After condensation with ethyl cyclopentan-2-one carboxylate and ethyl cyclohexan-2-one carboxylate, copper-catalyzed Michael reactions of the resulting enamines 2 with methyl vinyl ketone were carried out at 23 °C for two days in acetone to give ethyl (R)-2-oxo-1-(3-oxobutyl)cyclopentane carboxylate and ethyl-(R) 2-oxo-1-(3-oxobutyl)cyclohexane carboxylate with 99% ee and 97% ee, respectively. Auxiliary 1 was recovered by simple precipitation from diethyl ether.

ChemInform Abstract: New Chiral Auxiliaries for the Construction of Quaternary Stereocenters by Copper‐Catalyzed Michael Reactions.

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New Chiral Auxiliaries for the Construction of Quaternary Stereocenters by Copper-Catalyzed Michael Reactions This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. We are also grateful to the Degussa-Hüls AG for gifts of amino acids and to Prof. Dr. S. Blechert for his support.

New Chiral Auxiliaries for the Construction of Quaternary Stereocenters by Copper-Catalyzed Michael Reactions This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. We are also grateful to the Degussa-Hüls AG for gifts of amino acids and to Prof. Dr. S. Blechert for his support.