Highly Enantioselective Hydrogenation of Quinoline and Pyridine Derivatives with Iridium-(P-Phos) Catalyst
文献类型：期刊论文
| 作者 | Tang, Wei-Jun1,2,3; Tan, Jing1; Xu, Li-Jin1; Lam, Kim-Hung2,3; Fan, Qing-Hua4; Chan, Albert S. C.2,3 |
| 刊名 | ADVANCED SYNTHESIS & CATALYSIS
 |
| 出版日期 | 2010-04-01 |
| 卷号 | 352期号:6页码:1055-1062 |
| 关键词 | Asymmetric Hydrogenation Iridium Catalysis P-phos Pyridines Quinolines |
| ISSN号 | 1615-4150 |
| DOI | 10.1002/adsc.200900870 |
| 英文摘要 | The 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. |
| 语种 | 英语 |
| WOS记录号 | WOS:000277298800017 |
| 出版者 | WILEY-BLACKWELL |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/69899]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Xu, Li-Jin |
| 作者单位 | 1.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 |
| 推荐引用方式 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. |
入库方式： OAI收割
来源：化学研究所
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