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Influence of the double-bond geometry of the Michael acceptor on copper-catalysed asymmetric conjugate addition

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Published in European Journal of Organic Chemistry. 2007, no. 35, p. 5852-5860
Abstract Focusing on mechanistic aspects, a study of the influence of the (E)/(Z) double-bond geometry of the Michael acceptor on the enantioselectivity of copper-catalyzed asymmetric conjugate addition reactions has been realized. In spite of numerous articles concerning copper-catalyzed asymmetric conjugate addition reactions, the major factors of such a reaction are quite difficult to elucidate. Although our experiments have not allowed us to define strict rules, they have highlighted some factors not to be neglected when considering the approach of the copper reagent to the double bond, such as (E)/(Z) isomerization and steric aspects, which could change the reactive conformation of the substrate. Electronic effects could also modify the polarization of the double bond and influence the nucleophilic attack.
Keywords Michael additionAsymmetric catalysisDiethylzincCopperDouble-bond geometry
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VUAGNOUX-D'AUGUSTIN DE, Magali, ALEXAKIS, Alexandre. Influence of the double-bond geometry of the Michael acceptor on copper-catalysed asymmetric conjugate addition. In: European Journal of Organic Chemistry, 2007, n° 35, p. 5852-5860. https://archive-ouverte.unige.ch/unige:8131

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Deposited on : 2010-06-21

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