Hydrogen bonding-promoted efficient Ru-catalyzed ring-closing metathesis of demanding homoallyl 2-(hydroxymethyl)acrylates
Feng, Liang1; Liu, Yuehui1; Hou, Bo2; Yuan, Zaifeng1; Yu, Fu-Chao1; Yan, Tingbin1; Qin, Qi1; Ji, Ruigeng1; Li, Ya-Min1; Shen, Yuehai1; Zuo, Zhi-Li2
2016
发表期刊ORGANIC & BIOMOLECULAR CHEMISTRY
卷号14期号:45页码:10705-10713
摘要An efficient hydrogen bonding-guided ring-closing metathesis (RCM) reaction of sterically demanding homoallyl 2-(hydroxymethyl)acrylates catalyzed by the Hoveyda-Grubbs 2nd generation catalyst was developed and the reaction mechanism was explored. Adding a substituent to the hydroxymethyl group in this scaffold resulted in a class of challenging RCM substrates, although usable yields could be obtained. However, substrates bearing a 1-oxygenated alkyl group on the homoallylic carbon gave excellent RCM yields, providing a practical solution. Experimental and computational evidence indicated an unusual directing effect of OH center dot center dot center dot Cl hydrogen bonding between the substrate and Ru catalyst, which guides Ru to interact with the electron-deficient, more hindered acrylic C=C bond and thus triggers the RCM process.
DOI10.1039/c6ob02129h
收录类别SCI
语种英语
WOS记录号WOS:000388923600021
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被引频次:9[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/33774
专题植物化学与西部植物资源持续利用国家重点实验室
作者单位1.Kunming Univ Sci & Technol, Fac Life Sci & Technol, Kunming 650500, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China
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Feng, Liang,Liu, Yuehui,Hou, Bo,et al. Hydrogen bonding-promoted efficient Ru-catalyzed ring-closing metathesis of demanding homoallyl 2-(hydroxymethyl)acrylates[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2016,14(45):10705-10713.
APA Feng, Liang.,Liu, Yuehui.,Hou, Bo.,Yuan, Zaifeng.,Yu, Fu-Chao.,...&Zuo, Zhi-Li.(2016).Hydrogen bonding-promoted efficient Ru-catalyzed ring-closing metathesis of demanding homoallyl 2-(hydroxymethyl)acrylates.ORGANIC & BIOMOLECULAR CHEMISTRY,14(45),10705-10713.
MLA Feng, Liang,et al."Hydrogen bonding-promoted efficient Ru-catalyzed ring-closing metathesis of demanding homoallyl 2-(hydroxymethyl)acrylates".ORGANIC & BIOMOLECULAR CHEMISTRY 14.45(2016):10705-10713.
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