Nickel‐Catalyzed Asymmetric Synthesis of α‐Arylbenzamides
Sergio Cuesta‐Galisteo, Johannes Schörgenhumer, Xiaofeng Wei, Estı́baliz Merino, Cristina Nevado
Abstract
Abstract A nickel‐catalyzed asymmetric reductive hydroarylation of vinyl amides to produce enantioenriched α‐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 α 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.
Topics & Concepts
StereocenterChemistryArylCombinatorial chemistryRegioselectivityNickelCatalysisOlefin fiberReagentLigand (biochemistry)HalideAtom economyAryl halideStereochemistryPalladiumEnantioselective synthesisOrganic chemistryReceptorAlkylBiochemistryCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisSynthesis and Catalytic Reactions