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题名: Solvent-Regulated Asymmetric Hydrogenation of Quinoline Derivatives in Oligo(Ethylene Glycol)s through Host-Guest Interactions
作者: Wang, Tianli1, 2; Chen, Ya1, 2; Ouyang, Guanghui1, 2; He, Yan-Mei1, 2; Li, Zhiyan1, 2; Fan, Qing-Hua1, 2, 3
关键词: asymmetric catalysis ; hydrogenation ; oligo(ethylene glycol)s ; ruthenium ; solvent effects
刊名: CHEMISTRY-AN ASIAN JOURNAL
发表日期: 2016-10-01
卷: 11, 期:19, 页:2773-2777
收录类别: SCI
英文摘要: The asymmetric hydrogenation of quinolines in oligo(ethylene glycol)s (OEGs) and poly(ethylene glycol)s (PEGs) with chiral cationic ruthenium diamine complexes has been investigated. Interestingly, in liquid PEGs or long-chain OEGs, the Ru catalysts lost their reactivity. Upon the addition of a little MeOH, the hydrogenation of quinoline was switched "ON". Evidence from mass spectrometry and control experiments revealed that encapsulation of the quinolinium salt by PEG or long-chain OEG molecules through supramolecular interactions is possibly the main reason for such a switchable hydrogenation reaction. Moreover, the asymmetric hydrogenation of 2-substituted quinoline derivatives was achieved in triethylene glycol (3-OEG), thereby affording 1,2,3,4-tetrahydroquinolines with excellent reactivities and enantioselectivities (up to 99% ee). Furthermore, the Ru catalyst could be readily recycled for both pure 3-OEG and biphasic 3-OEG/n-hexane systems without a clear loss of reactivity and enantioselectivity.
语种: 英语
内容类型: 期刊论文
URI标识: http://ir.iccas.ac.cn/handle/121111/35126
Appears in Collections:分子识别与功能实验室_期刊论文

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作者单位: 1.Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100190, Peoples R China
3.Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China
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