Highly enantioselective and regioselective copper-catalyzed 1,4 addition of grignard reagents to cyclic enynones. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2011

Highly enantioselective and regioselective copper-catalyzed 1,4 addition of grignard reagents to cyclic enynones.

Résumé

In this letter we describe an unusual result in terms of regioselectivity with respect to copper-catalyzed conjugate additions of various Grignard reagents to cyclic enynones. The use of Cu(OTf)(2) and NHC ligand L1 as the catalyst combination in CH(2)Cl(2) led to the unique formation of the 1,4 adduct. This selectivity does not follow the general trend previously observed in the literature using extended Michael acceptors. Moreover these reactions allowed for the creation of a quarternary stereogenic center with enantioselectivities up to 97% ee.

Domaines

Chimie organique
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Dates et versions

hal-00754924 , version 1 (20-11-2012)

Identifiants

Citer

Matthieu Tissot, Alexandra Pérez Hernández, Daniel Müller, Marc Mauduit, Alexandre Alexakis. Highly enantioselective and regioselective copper-catalyzed 1,4 addition of grignard reagents to cyclic enynones.. Organic Letters, 2011, 13 (6), pp.1524-7. ⟨10.1021/ol200219m⟩. ⟨hal-00754924⟩
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