Gold-Catalyzed Intermolecular Reactions of Propiolic Acids with Alkenes: [4+2] Annulation and Enyne Cross Metathesis

doi:10.1021/ja210792e

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	Gold-Catalyzed Intermolecular Reactions of Propiolic Acids with Alkenes: [4+2] Annulation and Enyne Cross Metathesis
	Yeom, Hyun-Suk 2,3; Koo, Jaeyoung 2,3; Park, Hyun-Sub 2,3; Wang, Yi 1; Liang, Yong 1; Yu, Zhi-Xiang 1; Shin, Seunghoon 2,3
刊名	JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
	2012-01-11
卷号	134 期号:1 页码:208-211
ISSN号	0002-7863
DOI	10.1021/ja210792e
英文摘要	A gold-catalyzed intermolecular reaction of propiolic acids with alkenes led to a [4 + 2] annulation or enyne cross metathesis. The [4 + 2] annulation proceeds with net cis-addition with respect to alkenes and provides an expedient route to alpha,beta-unsaturated delta-lactones, for which preliminary asymmetric reactions were also demonstrated. For 1,2-disubstituted alkenes, unprecedented enyne cross metathesis occurred to give I,3-dienes in a completely stereospecific fashion. DFT calculations and experiments indicated that the cyclobutene derivatives are not viable intermediates and that the steric interactions during concerted sigma-bond rearrangements are responsible for the observed unique stereospecificity.
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000301084200055
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/49319]
专题	中国科学院化学研究所
通讯作者	Yu, Zhi-Xiang
作者单位	1.Peking Univ, Coll Chem, BNLMS, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China 2.Hanyang Univ, Dept Chem, Seoul 133791, South Korea 3.Hanyang Univ, Res Inst Nat Sci, Seoul 133791, South Korea
推荐引用方式 GB/T 7714	Yeom, Hyun-Suk,Koo, Jaeyoung,Park, Hyun-Sub,et al. Gold-Catalyzed Intermolecular Reactions of Propiolic Acids with Alkenes: [4+2] Annulation and Enyne Cross Metathesis[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2012,134(1):208-211.
APA	Yeom, Hyun-Suk.,Koo, Jaeyoung.,Park, Hyun-Sub.,Wang, Yi.,Liang, Yong.,...&Shin, Seunghoon.(2012).Gold-Catalyzed Intermolecular Reactions of Propiolic Acids with Alkenes: [4+2] Annulation and Enyne Cross Metathesis.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,134(1),208-211.
MLA	Yeom, Hyun-Suk,et al."Gold-Catalyzed Intermolecular Reactions of Propiolic Acids with Alkenes: [4+2] Annulation and Enyne Cross Metathesis".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 134.1(2012):208-211.