3 years ago

N-heterocyclic Carbene–Cu-Catalyzed Enantioselective Conjugate Additions with Alkenylboronic Esters as Nucleophiles

N-heterocyclic Carbene–Cu-Catalyzed Enantioselective Conjugate Additions with Alkenylboronic Esters as Nucleophiles
Qinglei Chong, Zhenting Yue, Chonglei Ji, Fanke Meng, Xin Hong, Haiyan Zhang, Fengchang Cheng, Shuoqing Zhang
Catalytic enantioselective conjugate additions with easily accessible alkenylboronic acid pinacol esters as nucleophiles promoted by chiral copper complexes of N-heterocyclic carbenes are presented. These processes constitute an unprecedented instance of conjugate additions of a variety of functionalized alkenyl groups and afford desired products that are otherwise difficult to access in up to 98% yield and 99.5:0.5 enantiomeric ratio. The origins of ligand-controlled enantioselectivity are elucidated with density functional theory (DFT) calculations.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b02132

DOI: 10.1021/acscatal.7b02132

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