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Copper‐Catalyzed Asymmetric Conjugate Addition of Dimethylzinc to Acyl‐ N ‐methylimidazole Michael Acceptors: a Powerful Synthetic Platform
Author(s) -
DrissiAmraoui Sammy,
Morin Marie S. T.,
Crévisy Christophe,
Baslé Olivier,
Marcia de Figueiredo Renata,
Mauduit Marc,
Campagne JeanMarc
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201506189
Subject(s) - dimethylzinc , conjugate , chemistry , enantioselective synthesis , michael reaction , catalysis , denticity , addition reaction , ligand (biochemistry) , adduct , copper , combinatorial chemistry , organic chemistry , mathematical analysis , biochemistry , receptor , mathematics , crystal structure
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.).