| 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
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| 2016 | |
| 发表期刊 | ORGANIC & BIOMOLECULAR CHEMISTRY
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| 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. |
| DOI | 10.1039/c6ob02129h |
| 收录类别 | SCI |
| 语种 | 英语 |
| WOS记录号 | WOS:000388923600021 |
| 引用统计 | |
| 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 |
| 推荐引用方式 GB/T 7714 | 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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| feng2016.pdf（1602KB） | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | 浏览 下载 | |
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