Platinum-Catalyzed Tandem Cycloisomerization Reaction of Benzoendiynyl Esters: Regioselective Long-Range 1,5-Acyl Migration

被引：22
|
作者：
Chen, Zhiyuan [1 ]
Jia, Xuegong
Huang, Jiapian
Yuan, Jianjun
机构：
[1] Jiangxi Normal Univ, Key Lab Funct Small Organ Mol, Minist Educ, Nanchang 330022, Jiangxi, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 21期
基金：
中国国家自然科学基金;
关键词：
CARBON-MONOXIDE; GOLD; CYCLIZATION; ACTIVATION; PALLADIUM; 1,6-ENYNES; EFFICIENT; ACCESS; REARRANGEMENT; CYCLOADDITION;
D O I：
10.1021/jo5020245
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Pt-II-catalyzed intramolecular chemo- and regioselective pentannulation/long-range 1,5-acyl migration reaction is described. This cascade cycloisomerization protocol produces a wide variety of benzofulvene diketones in good to excellent yields with exclusively the Z configuration of the exocyclic double bond of the final product. The O-18 isotope experiment together with C-13 NMR, HRMS, and HMBC analyses confirmed an interesting long-range acyl rearrangement process in this transformation.
引用
收藏
页码：10674 / 10681
页数：8
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