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

Autor:	Drissi ‐ Amraoui, Sammy, Morin, Marie S. T., Crévisy, Christophe, Baslé, Olivier, Marcia de Figueiredo, Renata, Mauduit, Marc, Campagne, Jean ‐ Marc
Předmět:	COPPER catalysts CONJUGATE addition reactions DIMETHYLZINC CHEMICAL adducts NUCLEOPHILES
Zdroj:	Angewandte Chemie; Sep2015, Vol. 127 Issue 40, p11996-12000, 5p
Abstrakt:	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.). [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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