ICCAS OpenIR
Gold Catalyzed Carbocyclization of Dienyl Acetates to Construct Mutifunctionalized 3-Vinyl Cyclohexanol Derivatives
Zhu, Li-Li1; Wang, Ya-Hui1; Zhang, Yu-Xin1; Li, Xiao-Xiao1; Liu, Heng1; Chen, Zili1,2
2011-01-21
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume76Issue:2Pages:441-449
AbstractA convenient new method was developed to construct six-membered 3-vinylcyclohexanols (and piperidine products) and 6-oxabicyclo[3.2.1]octan-7-one derivatives with high diastereoselectivities from 1,6-dienyl acetates via gold catalysis. The reaction proceeded through the nucleophilic addition of the alkenes onto the allylic cation group via a 6-endo-trig process. The substrate's structure affected the configuration orientation of the allylic cation group in a boatlike transition state, which afforded either the trans-cyclohexanols or cis-piperidine derivatives.
DOI10.1021/jo1018014
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000286129900012
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:10[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/72234
Collection中国科学院化学研究所
Corresponding AuthorChen, Zili
Affiliation1.Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China
2.Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Zhu, Li-Li,Wang, Ya-Hui,Zhang, Yu-Xin,et al. Gold Catalyzed Carbocyclization of Dienyl Acetates to Construct Mutifunctionalized 3-Vinyl Cyclohexanol Derivatives[J]. JOURNAL OF ORGANIC CHEMISTRY,2011,76(2):441-449.
APA Zhu, Li-Li,Wang, Ya-Hui,Zhang, Yu-Xin,Li, Xiao-Xiao,Liu, Heng,&Chen, Zili.(2011).Gold Catalyzed Carbocyclization of Dienyl Acetates to Construct Mutifunctionalized 3-Vinyl Cyclohexanol Derivatives.JOURNAL OF ORGANIC CHEMISTRY,76(2),441-449.
MLA Zhu, Li-Li,et al."Gold Catalyzed Carbocyclization of Dienyl Acetates to Construct Mutifunctionalized 3-Vinyl Cyclohexanol Derivatives".JOURNAL OF ORGANIC CHEMISTRY 76.2(2011):441-449.
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