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Highly Enantioselective Hydrogenation of Quinoline and Pyridine Derivatives with Iridium-(P-Phos) Catalyst
Tang, Wei-Jun1,2,3; Tan, Jing1; Xu, Li-Jin1; Lam, Kim-Hung2,3; Fan, Qing-Hua4; Chan, Albert S. C.2,3
2010-04-01
Source PublicationADVANCED SYNTHESIS & CATALYSIS
ISSN1615-4150
Volume352Issue:6Pages:1055-1062
AbstractThe use of a chiral iridium catalyst generated in situ from the (cyclooctadiene)iridium chloride 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 hydrogenation of 2,6-substituted quinolines and trisubstituted pyridines [2-substituted 7,8-dihydroquinolin-5(6H)one derivatives] is reported. The catalyst worked efficiently to hydrogenate a series of quinoline derivatives to provide chiral 1,2,3,4-tetrahydroquinolines in high yields and up to 96% cc. 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 (turnover number). The catalytic activity is found to be additive-controlled. At low catalyst loadings, decreasing the amount of additive I(2) was necessary to maintain the good conversion. The same catalyst system could also enantioselectively hydrogenate trisubstituted pyridines, affording the chiral hexahydroquinolinone derivatives in nearly quantitative yields and up to 99% cc. Interestingly, increasing the amount of I(2) favored high reactivity and enantioselectivity in this case. The high efficacy and enantioselectivity enable the present catalyst system of high practical potential.
KeywordAsymmetric Hydrogenation Iridium Catalysis P-phos Pyridines Quinolines
DOI10.1002/adsc.200900870
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000277298800017
PublisherWILEY-BLACKWELL
Citation statistics
Cited Times:73[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/69900
Collection中国科学院化学研究所
Corresponding AuthorXu, Li-Jin
Affiliation1.Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China
2.Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China
3.Hong Kong Polytech Univ, Open Lab Chirotechnol, Inst Mol Technol Drug Discovery & Synth, Hong Kong, Hong Kong, Peoples R China
4.Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Tang, Wei-Jun,Tan, Jing,Xu, Li-Jin,et al. Highly Enantioselective Hydrogenation of Quinoline and Pyridine Derivatives with Iridium-(P-Phos) Catalyst[J]. ADVANCED SYNTHESIS & CATALYSIS,2010,352(6):1055-1062.
APA Tang, Wei-Jun,Tan, Jing,Xu, Li-Jin,Lam, Kim-Hung,Fan, Qing-Hua,&Chan, Albert S. C..(2010).Highly Enantioselective Hydrogenation of Quinoline and Pyridine Derivatives with Iridium-(P-Phos) Catalyst.ADVANCED SYNTHESIS & CATALYSIS,352(6),1055-1062.
MLA Tang, Wei-Jun,et al."Highly Enantioselective Hydrogenation of Quinoline and Pyridine Derivatives with Iridium-(P-Phos) Catalyst".ADVANCED SYNTHESIS & CATALYSIS 352.6(2010):1055-1062.
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