Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 17, Issue 20, Pages 5099-5105Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9ob00770a
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Funding
- National Natural Science Foundation of China (NSFC) [21790332, 21521002, 21672218]
- CAS [QYZDJSSWSLH023]
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A small library of tunable chiral pyridine-aminophosphine ligands were enantioselectively synthesized based on chiral 2-(pyridin-2-yl)-substituted 1,2,3,4-tetrahydroquinoline scaffolds, which were obtained in high yields and with excellent enantioselectivities via ruthenium-catalyzed asymmetric hydrogenation of 2-(pyridin-2-yl)quinolines. The protocol features a wide substrate scope and mild reaction conditions, enabling scalable synthesis. These chiral P,N ligands were successfully applied in the Ir-catalyzed asymmetric hydrogenation of benchmark olefins and challenging seven-membered cyclic imines including benzazepines and benzodiazepines. Excellent enantio-and diastereoselectivity (up to 99% ee and >20 : 1 dr), and/or unprecedented chemoselectivity were obtained in the asymmetric hydrogenation of 2,4-diaryl-3H-benzo[b]azepines and 2,4-diaryl-3H-benzo[ b][1,4]diazepines.
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