Nickel-Catalyzed Asymmetric Synthesis of alpha-Arylbenzamides

摘要

A nickel-catalyzed asymmetric reductive hydroarylation of vinyl amides to produce enantioenriched alpha-arylbenzamides is reported. The use of a chiral bisimidazoline (BIm) ligand, in combination with diethoxymethylsilane and aryl halides, enables the regioselective introduction of aryl groups to the internal position of the olefin, forging a new stereogenic center alpha to the N atom. The use of neutral reagents and mild reaction conditions provides simple access to pharmacologically relevant motifs present in anticancer, SARS-CoV PLpro inhibitors, and KCNQ channel openers.