Copper-Catalyzed Asymmetric Conjugate Additions of Bis(pinacolato)diboron and Dimethylzinc to Acyl- N -methylimidazole Michael Acceptors: A Highly Stereoselective Unified Strategy for 1,3,5,... n (OH, Me) Motif Synthesis - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2019

Copper-Catalyzed Asymmetric Conjugate Additions of Bis(pinacolato)diboron and Dimethylzinc to Acyl- N -methylimidazole Michael Acceptors: A Highly Stereoselective Unified Strategy for 1,3,5,... n (OH, Me) Motif Synthesis

Résumé

A unified strategy for the construction of prevalent 1,3,5,...n (OH, Me) motifs based on consecutive copper-catalyzed asymmetric conjugate borylation (ACB) and methylation (ACA) reactions involving α,β-unsaturated 2-acyl-N-methylimidazoles is described. Good yields and high diastereoselectivities have been obtained in ACA and ACB reactions for both matched and mismatched pairs as illustrated in the synthesis of syn/anti and anti/anti (Me, OTBS,Me) and (OH, OTBS, Me) motifs.

Domaines

Chimie organique
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Dates et versions

hal-02080938 , version 1 (27-03-2019)

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Citer

Jimmy Lauberteaux, Christophe Crevisy, Olivier Baslé, Renata Marcia de Figueiredo, Marc Mauduit, et al.. Copper-Catalyzed Asymmetric Conjugate Additions of Bis(pinacolato)diboron and Dimethylzinc to Acyl- N -methylimidazole Michael Acceptors: A Highly Stereoselective Unified Strategy for 1,3,5,... n (OH, Me) Motif Synthesis. Organic Letters, 2019, 21 (6), pp.1872-1876. ⟨10.1021/acs.orglett.9b00479⟩. ⟨hal-02080938⟩
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