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Asymmetric Hydrogenation of Cyclic Imines of Benzoazepines and Benzodiazepines with Chiral, Cationic Ruthenium–Diamine Catalysts
Author(s) -
Yang Zhusheng,
Ding Ziyuan,
Chen Fei,
He YanMei,
Yang Nianfa,
Fan QingHua
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700236
Subject(s) - enantioselective synthesis , chemistry , ruthenium , cationic polymerization , diamine , asymmetric hydrogenation , catalysis , enantiomer , noyori asymmetric hydrogenation , optically active , medicinal chemistry , organic chemistry , combinatorial chemistry , stereochemistry
A method for the highly enantioselective hydrogenation of diverse seven‐membered N‐containing heterocycles, including 2,4‐diaryl‐3 H ‐benzo[ b ]azepines, racemic 2,2,4‐trisubstituted 2,3‐dihydrobenzo[ b ][1,4]diazepines, and 4‐substituted 1 H ‐benzo[ b ][1,4]diazepin‐2(3 H )‐ones by using chiral, cationic ruthenium–diamine catalysts was developed. Reversal of enantioselectivity was observed for all of these substrates simply by changing the achiral counteranion of the catalyst. This method thus provided facile access to both enantiomers of these optically pure seven‐membered heterocycles.