Copper-Catalyzed Asymmetric Conjugate Addition of Dimethylzinc to Acyl- \textitN -methylimidazole Michael Acceptors: a Powerful Synthetic Platform - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Angewandte Chemie Année : 2015

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

Résumé

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.).

Dates et versions

hal-01236436 , version 1 (01-12-2015)

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Citer

Sammy Drissi-Amraoui, Marie S. T. Morin, Christophe Crévisy, Olivier Baslé, Renata Marcia de figueiredo, et al.. Copper-Catalyzed Asymmetric Conjugate Addition of Dimethylzinc to Acyl- \textitN -methylimidazole Michael Acceptors: a Powerful Synthetic Platform. Angewandte Chemie, 2015, 127 (40), pp.11996--12000. ⟨10.1002/ange.201506189⟩. ⟨hal-01236436⟩
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