Copper-Catalyzed Asymmetric Conjugate Addition of Dimethyl-zinc to Acyl-N-methylimidazole Michael Acceptors: Scope,Limitations and Iterative Reactions - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2016

Copper-Catalyzed Asymmetric Conjugate Addition of Dimethyl-zinc to Acyl-N-methylimidazole Michael Acceptors: Scope,Limitations and Iterative Reactions

Olivier Baslé
Stéphanie Halbert

Résumé

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 DFTstudies 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.

Dates et versions

hal-01355326 , version 1 (23-08-2016)

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Citer

Sammy Drissi Amraoui, Thibault E. Schmid, Jimmy Lauberteaux, Christophe Crevisy, Olivier Baslé, et al.. Copper-Catalyzed Asymmetric Conjugate Addition of Dimethyl-zinc to Acyl-N-methylimidazole Michael Acceptors: Scope,Limitations and Iterative Reactions. Advanced Synthesis and Catalysis, 2016, 358 (15), pp.2519-2540. ⟨10.1002/adsc.201600458⟩. ⟨hal-01355326⟩
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