title: Asymmetric ruthenium-catalyzed hydrogenation of 2,6-disubstituted 1,5-naphthyridines: access to chiral 1,5-diaza-cis-decalins.
abstract: 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.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences (ICCAS), Beijing 100190 (P. R. China); Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072 (P. R. China).
authors.forename: Jianwei
authors.initials: J
authors.lastname: Zhang
authors.forename: Fei
authors.initials: F
authors.lastname: Chen
authors.forename: Yan-Mei
authors.initials: YM
authors.lastname: He
authors.forename: Qing-Hua
authors.initials: QH
authors.lastname: Fan
mesh_terms: D002384:Catalysis; D003959:Diamines / Q000737:chemistry; D006865:Hydrogenation; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D009287:Naphthyridines / Q000138:chemical synthesis / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D003959:Diamines; D009281:Naphthalenes; D009287:Naphthyridines; D012428:Ruthenium; C007229:decalin
keywords: asymmetric catalysis; enantioselectivity; heterocycles; hydrogenation; ruthenium