Hydrogen bonding-promoted efficient Ru-catalyzed ring-closing metathesis of demanding homoallyl 2-(hydroxymethyl)acrylates

CORC > 昆明植物研究所 > 中国科学院昆明植物研究所 > 植物化学与西部植物资源持续利用国家重点实验室

	Hydrogen bonding-promoted efficient Ru-catalyzed ring-closing metathesis of demanding homoallyl 2-(hydroxymethyl)acrylates
	Feng, Liang 1; Liu, Yuehui 1; Hou, Bo 2; Yuan, Zaifeng 1; Yu, Fu-Chao 1; Yan, Tingbin 1; Qin, Qi 1; Ji, Ruigeng 1; Li, Ya-Min 1; Shen, Yuehai 1
刊名	ORGANIC & BIOMOLECULAR CHEMISTRY
	2016
卷号	14 期号:45 页码:10705-10713
英文摘要	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.
类目[WOS]	Chemistry, Organic
研究领域[WOS]	Chemistry
关键词[WOS]	FORM TETRASUBSTITUTED OLEFINS ; CONCISE TOTAL-SYNTHESIS ; (+)-BORONOLIDE ; DERIVATIVES ; INHIBITOR ; (+)-STRICTIFOLIONE ; DENOSOMIN ; LACTONES ; ROUTE
收录类别	SCI
语种	英语
WOS记录号	WOS:000388923600021
内容类型	期刊论文
源URL	[http://ir.kib.ac.cn/handle/151853/33774]
专题	昆明植物研究所_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.