Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 22, Pages 4319-4324Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201800839
Keywords
Asymmetric hydrogenation; Benzo-fused cyclic ketone; Chiral benzo-fused cyclic alcohol; Enantioselectivity; Phosphorus ligand
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Funding
- National Natural Science Foundation of China [21432007, 21502145]
- Natural Science Foundation of Hubei Province [2016CFB449]
- Wuhan Morning Light Plan of Youth Science and Technology [2017050304010307]
- Shenzhen Nobel Prize Scientists Laboratory Project [C17213101]
- Fundamental Research Funds for and the Central Universities [2042018kf0202]
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Iridium/f-Amphol-catalyzed asymmetric hydrogenation of various benzo-fused five to seven-membered cyclic ketones was successfully developed, affording a series of chiral benzo-fused cyclic alcohols with excellent results (75%-99% yields, 93%->99% ee, and TON up to 297 000). The enantioenriched products can be employed as key intermediates or motifs for the synthesis of some important biologically active compounds, such as rasagiline mesylate TVP-1012 used for the treatment of Parkinson's disease, the enantiomer of anticonvulsant drug eslicarbazepine acetate (BIA 2-093).
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