Asymmetric Ruthenium‐Catalyzed Hydrogenation of 2,6‐Disubstituted 1,5‐Naphthyridines: Access to Chiral 1,5‐Diaza‐cis‐Decalins |
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| Authors: | Jianwei Zhang Fei Chen Yan‐Mei He Prof?Dr Qing‐Hua Fan |
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| Institution: | 1. 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);2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072 (P. R. China) |
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| 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. |
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| Keywords: | asymmetric catalysis enantioselectivity heterocycles hydrogenation ruthenium |
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