Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/22884
Title: Highly enantioselective hydrogenation of quinoline and pyridine derivatives with iridium-(P-Phos) catalyst
Authors: Tang, WJ
Tan, J
Xu, LJ
Lam, KH
Fan, QH
Chan, ASC
Keywords: Asymmetric hydrogenation
Iridium catal-ysis
P-Phos
Pyridines
Quinolines
Issue Date: 2010
Publisher: Wiley-VCH
Source: Advanced synthesis & catalysis, 2010, v. 352, no. 6, p. 1055-1062 How to cite?
Journal: Advanced synthesis & catalysis 
Abstract: The use of a chiral iridium catalyst gener-ated in situ from the (cyclooctadiene)iridium chlo-ride dimer, [Ir(COD)Cl] 2, the P-Phos ligand [4, 4'-bis(diphenylphosphino)-2, 2', 6, 6'-tetramethoxy-3, 3'-bi-pyridine] and iodine (I 2) for the asymmetric hydroge-nation of 2, 6-substituted quinolines and trisubstituted pyridines [2-substituted 7, 8-dihydroquinolin-5(6H)-one derivatives] is reported. The catalyst worked ef-ficiently to hydrogenate a series of quinoline deriva-tives to provide chiral 1, 2, 3, 4-tetrahydroquinolines in high yields and up to 96% ee. The hydrogenation was carried out at high S/C (substrate to catalyst) ratios of 2000-50000, reaching up to 4000 h -1 TOF (turnover frequency) and up to 43000 TON (turn-over number). The catalytic activity is found to be additive-controlled. At low catalyst loadings, de-creasing the amount of additive I 2 was necessary to maintain the good conversion. The same catalyst system could also enantioselectively hydrogenate tri-substituted pyridines, affording the chiral hexahydro-quinolinone derivatives in nearly quantitative yields and up to 99% ee. Interestingly, increasing the amount of I 2 favored high reactivity and enantiose-lectivity in this case. The high efficacy and enantiose-lectivity enable the present catalyst system of high practical potential.
URI: http://hdl.handle.net/10397/22884
ISSN: 1615-4150
EISSN: 1615-4169
DOI: 10.1002/adsc.200900870
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