Rhodium-Catalyzed Intramolecular [5+2] Cycloaddition of Inverted 3-Acyloxy-1,4-enyne and Alkyne: Experimental and Theoretical Studies

被引：14

作者：

Li, Xiaoxun ^{[1
]}

Song, Wangze ^{[1
]}

Ke, Xiaona ^{[2
]}

Xu, Xiufang ^{[2
]}

Liu, Peng ^{[3
]}

Houk, K. N. ^{[4
]}

Zhao, Xian-liang ^{[1
,5
]}

Tang, Weiping ^{[1
,6
]}

机构：

[1] Univ Wisconsin, Sch Pharm, 425 N Charter St, Madison, WI 53706 USA

[2] Nankai Univ, Dept Chem, Key Lab Adv Energy Mat Chem, Minist Educ, Tianjin 300071, Peoples R China

[3] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

[4] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[5] Zhejiang Univ Sci & Technol, Sch Biol & Chem Engn, Hangzhou 310023, Zhejiang, Peoples R China

[6] Univ Wisconsin, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 21期

基金：

美国国家科学基金会; 中国国家自然科学基金;

关键词：

catalysis; cycloaddition; enynes; rhodium; seven-membered rings; DENSITY-FUNCTIONAL THEORY; DIELS-ALDER REACTION; 7-MEMBERED RINGS; NATURAL SESQUITERPENOIDS; PROPARGYLIC ESTERS; VINYL AZIRIDINES; ENE REACTIONS; VINYLCYCLOPROPANES; MECHANISM; SELECTIVITY;

D O I：

10.1002/chem.201601195

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

By switching the position of the alkene and alkyne, a new type of 3-acyloxy-1,4-enyne (ACE) five-carbon building block was developed for Rh-catalyzed intramolecular [5+2] cycloaddition. An electron-withdrawing acyl group on the alkyne termini of the ACE was essential for a regioselective 1,2-acyloxy migration. This new method provided bicyclic [5.3.0]decatrienes that are different from previous methods because of the positions of the alkenes and the acyloxy group. Multiple mechanistic pathways become possible for this new [5+2] cycloaddition and they are investigated by computational studies.

引用

页码：7079 / 7083

页数：5

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