Highly Enantioselective Synthesis of Chiral Tetrahydroquinolines and Tetrahydroisoquinolines by Ruthenium-Catalyzed Asymmetric Hydrogenation in Ionic Liquid
文献类型：期刊论文
| 作者 | Ding, Zi-Yuan1,2,3; Wang, Tianli2,3; He, Yan-Mei2,3; Chen, Fei2,3; Zhou, Hai-Feng2,3; Fan, Qing-Hua2,3; Guo, Qingxiang1; Chan, Albert S. C.4 |
| 刊名 | ADVANCED SYNTHESIS & CATALYSIS
 |
| 出版日期 | 2013-12-16 |
| 卷号 | 355期号:18页码:3727-3735 |
| 关键词 | Asymmetric Hydrogenation Catalyst Recycling Ionic Liquids Tetrahydroisoquinolines Tetrahydroquinolines |
| ISSN号 | 1615-4150 |
| DOI | 10.1002/adsc.201300698 |
| 英文摘要 | Asymmetric hydrogenation reactions of quinolines and 3,4-dihydroisoquinolines using the chiral cationic ruthenium complex Ru(TsDPEN) [TsDPEN=N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine] as catalyst in neat imidazolium ionic liquids have been investigated. The catalytic performance was influenced by the anion of the ionic liquids for both substrate classes. A range of 2-alkyl-substituted 1,2,3,4-tetrahydroquinolines and 1-alkyl-substituted 1,2,3,4-tetrahydroisoquinolines was obtained in high yields with up to >99% ee. Interestingly, the hydrogenation of quinoline derivatives bearing a carbonyl group was selective for the CN (quinoline) over the CO (ketone) bonds, while such a unique chemoselectivity was not observed in methanol. Furthermore, the ruthenium catalysts could be easily recycled at least 5 times in the asymmetric hydrogenation of 3,4-dihydroisoquinoline by solvent extraction. To further facilitate the recovery of catalyst and reduce the use of organic solvent, a thin film of ionic liquid containing Ru(TsDPEN) was supported on silica gels. This supported ionic liquid-phase catalyst was effective in the asymmetric hydrogenation of quinoline, and could be recycled at least 6 times by simple filtration. |
| 语种 | 英语 |
| WOS记录号 | WOS:000329021600029 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/46421]  |
| 专题 | 中国科学院化学研究所 |
| 通讯作者 | Fan, Qing-Hua |
| 作者单位 | 1.Univ Sci & Technol China, Anhui Prov Key Lab Biomass Clean Energy, Dept Chem, Hefei 230026, Peoples R China 2.Chinese Acad Sci, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China 3.Chinese Acad Sci, Grad Sch, Beijing 100190, Peoples R China 4.Hong Kong Baptist Univ, Inst Creat, Hong Kong, Hong Kong, Peoples R China |
| 推荐引用方式 GB/T 7714 | Ding, Zi-Yuan,Wang, Tianli,He, Yan-Mei,et al. Highly Enantioselective Synthesis of Chiral Tetrahydroquinolines and Tetrahydroisoquinolines by Ruthenium-Catalyzed Asymmetric Hydrogenation in Ionic Liquid[J]. ADVANCED SYNTHESIS & CATALYSIS,2013,355(18):3727-3735. |
| APA | Ding, Zi-Yuan.,Wang, Tianli.,He, Yan-Mei.,Chen, Fei.,Zhou, Hai-Feng.,...&Chan, Albert S. C..(2013).Highly Enantioselective Synthesis of Chiral Tetrahydroquinolines and Tetrahydroisoquinolines by Ruthenium-Catalyzed Asymmetric Hydrogenation in Ionic Liquid.ADVANCED SYNTHESIS & CATALYSIS,355(18),3727-3735. |
| MLA | Ding, Zi-Yuan,et al."Highly Enantioselective Synthesis of Chiral Tetrahydroquinolines and Tetrahydroisoquinolines by Ruthenium-Catalyzed Asymmetric Hydrogenation in Ionic Liquid".ADVANCED SYNTHESIS & CATALYSIS 355.18(2013):3727-3735. |
入库方式： OAI收割
来源：化学研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。