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Nickel‐Catalyzed Asymmetric Synthesis of α‐Arylbenzamides
Author(s) -
CuestaGalisteo Sergio,
Schörgenhumer Johannes,
Wei Xiaofeng,
Merino Estíbaliz,
Nevado Cristina
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202011342
Subject(s) - stereocenter , chemistry , aryl , combinatorial chemistry , regioselectivity , nickel , catalysis , olefin fiber , reagent , ligand (biochemistry) , halide , atom economy , aryl halide , stereochemistry , palladium , enantioselective synthesis , organic chemistry , biochemistry , alkyl , receptor
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.