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- Title
Copper-Catalyzed Asymmetric Conjugate Addition of Dimethylzinc to Acyl- N-methylimidazole Michael Acceptors: Scope, Limitations and Iterative Reactions.
- Authors
Drissi ‐ Amraoui, Sammy; Schmid, Thibault E.; Lauberteaux, Jimmy; Crévisy, Christophe; Baslé, Olivier; de Figueiredo, Renata Marcia; Halbert, Stéphanie; Gérard, Hélène; Mauduit, Marc; Campagne, Jean ‐ Marc
- Abstract
An efficient copper-catalyzed enantioselective conjugate addition of dimethylzinc to unsaturated 2-acyl- N-methylimidazoles has been achieved using a chiral bidentate hydroxyalkyl-NHC ligand. The reactions proceed with excellent regioselectivity (1,4 vs. 1,6 and 1,8) in extended conjugated systems to afford the 1,4-adducts in high enantioselectivities. This regioselectivity could be ascertained by DFT studies highlighting the crucial role of the imidazole ring. Thanks to the development of efficient protocols to regenerate the unsaturated 2-acyl- N-methylimidazole moiety, an iterative process has been developed ultimately leading to 3,5,7 all-syn or anti-anti polydeoxypropionate stereodiads.
- Subjects
IMIDAZOLES; COPPER; ENANTIOSELECTIVE catalysis; DIMETHYLZINC; ZINC compounds
- Publication
Advanced Synthesis & Catalysis, 2016, Vol 358, Issue 15, p2519
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201600458