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Copper-catalyzed Asymmetric Conjugate Addition to Challenging Michael Acceptors and Synthesis of Relevant Target Molecules

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Published in Chimia. 2012, vol. 66, no. 4, p. 196-200
Abstract We report herein the enantioselective Cu-catalyzed conjugate addition of organometallic reagents to sensitive Michael acceptors and their application to the synthesis of relevant target molecules. This is one of the most important methodologies to form a C-C bond in an enantioselective manner. A wide range of α,β-unsaturated aldehydes and β,γ-unsaturated-α-ketoesters has been successfully used. Reactivity, regio- and enantioselectivities were strongly dependent on the reaction conditions, therefore moderate to very good results were obtained. Furthermore, γ-substituted-α-ketoesters were used as chiral building blocks for further derivatization with complete retention of the chiral information to obtain key compounds.
Keywords Asymmetric conjugate additionCopperOrganometallic reagentsα,β-unsaturated aldehydesβ,γ-unsaturated-α-ketoesters
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GREMAUD, Ludovic, PALAIS, Laetitia, ALEXAKIS, Alexandre. Copper-catalyzed Asymmetric Conjugate Addition to Challenging Michael Acceptors and Synthesis of Relevant Target Molecules. In: Chimia, 2012, vol. 66, n° 4, p. 196-200. https://archive-ouverte.unige.ch/unige:20284

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Deposited on : 2012-05-07

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