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- Title
Copper-Catalyzed Asymmetric Conjugate Addition of Dimethylzinc to Acyl- N-methylimidazole Michael Acceptors: a Powerful Synthetic Platform.
- Authors
Drissi ‐ Amraoui, Sammy; Morin, Marie S. T.; Crévisy, Christophe; Baslé, Olivier; Marcia de Figueiredo, Renata; Mauduit, Marc; Campagne, Jean ‐ Marc
- 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.).
- Subjects
COPPER catalysts; CONJUGATE addition reactions; DIMETHYLZINC; CHEMICAL adducts; NUCLEOPHILES
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 40, p11996
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201506189