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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202011342
Subject(s) - stereocenter , aryl , combinatorial chemistry , nickel , regioselectivity , chemistry , catalysis , reagent , olefin fiber , ligand (biochemistry) , halide , stereochemistry , organic chemistry , enantioselective synthesis , biochemistry , alkyl , receptor
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.