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Frontispiece: Cobalt‐Catalyzed Enantioselective Negishi Cross‐Coupling of Racemic α‐Bromo Esters with Arylzincs
Author(s) -
Liu Feipeng,
Zhong Jiangchun,
Zhou Yun,
Gao Zidong,
Walsh Patrick J.,
Wang Xueyang,
Ma Sijie,
Hou Shicong,
Liu Shangzhong,
Wang Minan,
Wang Min,
Bian Qinghua
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201880963
Subject(s) - negishi coupling , enantioselective synthesis , amide , chemistry , cobalt , catalysis , ether , olefin fiber , silyl ether , organic chemistry , acetal , halide , medicinal chemistry , silylation
An environmentally benign and high functional‐group‐tolerant synthesis of α‐arylalkanoic esters was found. This is the first cobalt‐catalyzed enantioselective Negishi cross‐coupling reaction, and the first arylation of α‐halo esters with arylzinc halides. Employing a cobalt‐bisoxazoline catalyst, various α‐arylalkanoic esters bearing ether, halide, thioether, silyl, amine, ester, acetal, amide, olefin and heteroaromatics functional groups were synthesized in excellent enantioselectivities and yields (64 examples, up to 97% ee and 98% yield) from racemic α‐bromo esters and arylzincs. This method was suitable for gram‐scale reactions, enabling the synthesis of ( R )‐xanthorrhizol with high enantiopurity. More information can be found in the Communication by J. Zhong, Q. Bian et al. on page 2059 ff.