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Kinetic Resolution of 2‐Substituted 1, 2‐Dihydroquinolines by Rhodium‐Catalyzed Asymmetric Hydroarylation †
Author(s) -
Cai Baohua,
Yang Qingjing,
Meng Ling,
Wang Jun Joelle
Publication year - 2021
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000742
Subject(s) - chemistry , rhodium , catalysis , kinetic resolution , aryl , asymmetric hydrogenation , medicinal chemistry , resolution (logic) , combinatorial chemistry , stereochemistry , organic chemistry , enantioselective synthesis , alkyl , artificial intelligence , computer science
Main observation and conclusion A highly efficient kinetic resolution of racemic 2‐substituted 1,2‐dihydroquinolines via Rh‐catalyzed asymmetric hydroarylation has been described for the first time. A variety of arylboronic acids coupled with 2‐substituted 1,2‐dihydroquinolines under mild reaction condition. The transformations into the enantio‐enriched 2,3‐diaryl‐tetrahydroquinolines as well as the recovered chiral 2‐aryl‐dihydroquinolines were obtained with high yields and excellent enantioselectivities (86%—99% ee , s factor up to 1057).