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Asymmetric Ruthenium‐Catalyzed Hydrogenation of 2,6‐Disubstituted 1,5‐Naphthyridines: Access to Chiral 1,5‐Diaza‐ cis ‐Decalins
Author(s) -
Zhang Jianwei,
Chen Fei,
He YanMei,
Fan QingHua
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201411105
Subject(s) - ruthenium , asymmetric hydrogenation , chemistry , diamine , catalysis , combinatorial chemistry , cationic polymerization , chelation , enantioselective synthesis , medicinal chemistry , stereochemistry , organic chemistry
The first asymmetric hydrogenation (AH) of 2,6‐disubstituted and 2,3,6‐trisubstituted 1,5‐naphthyridines, catalyzed by chiral cationic ruthenium diamine complexes, has been developed. A wide range of 1,5‐naphthyridine derivatives were efficiently hydrogenated to give 1,2,3,4‐tetrahydro‐1,5‐naphthyridines with up to 99 % ee and full conversions. This facile and green protocol is applicable to the scaled‐up synthesis of optically pure 1,5‐diaza‐ cis ‐decalins, which have been used as rigid chelating diamine ligands for asymmetric synthesis.