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Copper-Catalyzed Asymmetric Conjugate Addition of Dimethylzinc to Acyl-N-methylimidazole Michael Acceptors: a Powerful Synthetic Platform

Abstract : An efficient copper-catalyzed enantioselective conjugate addition of dimethylzinc to α,β- and α,β,γ,δ-unsaturated 2-acyl-N-methylimidazoles has been achieved using a chiral bidentate hydroxyalkyl-NHC ligand. The reactions proceeded with both excellent regio- and enantioselectivity (14 examples, 87-95 % ee) to afford the desired 1,4-adducts, which were easily transformed to the corresponding aldehydes, esters, and ketones. Subsequently, this powerful methodology was therefore successfully applied in the synthesis of natural products. Furthermore, an iterative process was also disclosed leading to highly desirable 1,3-desoxypropionate skeletons (up to 94 % d.e.).
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01188184
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Submitted on : Friday, August 28, 2015 - 3:23:05 PM
Last modification on : Friday, July 10, 2020 - 4:21:50 PM

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Sammy Drissi-Amraoui, Marcia de Figueiredo Renata, Jean-Marc Campagne, Marie S. T. Morin, Christophe Crévisy, et al.. Copper-Catalyzed Asymmetric Conjugate Addition of Dimethylzinc to Acyl-N-methylimidazole Michael Acceptors: a Powerful Synthetic Platform. Angewandte Chemie, Wiley-VCH Verlag, 2015, 54 (40), pp.11830-11834. ⟨10.1002/anie.201506189⟩. ⟨hal-01188184⟩

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