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Enantioselective Synthesis of 3,3′‐Disubstituted 2‐Amino‐2′‐hydroxy‐1,1′‐binaphthyls by Copper‐Catalyzed Aerobic Oxidative Cross‐Coupling
Author(s) -
Zhao XiaoJing,
Li ZiHao,
Ding TongMei,
Tian JinMiao,
Tu YongQiang,
Wang AiFang,
Xie YuYang
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202015001
Subject(s) - enantioselective synthesis , stacking , catalysis , chemistry , oxidative coupling of methane , oxidative phosphorylation , coupling (piping) , copper , combinatorial chemistry , stereochemistry , computational chemistry , medicinal chemistry , organic chemistry , materials science , biochemistry , metallurgy
A challenging direct asymmetric catalytic aerobic oxidative cross‐coupling of 2‐naphthylamine and 2‐naphthol, using a novel Cu I /SPDO system, has been successfully developed for the first time. Enantioenriched 3,3′‐disubstituted NOBINs were achieved and could be readily derived to divergent chiral ligands and catalysts. This reaction features high enantioselectivities (up to 96 % ee ) and good yields (up to 80 %). The DFT calculations suggest that the F–H interactions between CF 3 of L17 and H‐1,8 of 2‐naphthol, and the π–π stacking between the two coupling partners could play vital roles in the enantiocontrol of this cross‐coupling reaction.