Rhodium-Catalyzed [5+2] Cycloaddition of 3-Acyloxy-1,4-enyne with Alkene or Allene

被引：14

作者：

Song, Wangze ^{[1
]}

Lynch, John C. ^{[1
]}

Shu, Xing-zhong ^{[1
]}

Tang, Weiping ^{[1
,2
]}

机构：

[1] Univ Wisconsin Madison, Sch Pharm, Madison, WI 53705 USA

[2] Univ Wisconsin Madison, Dept Chem, Madison, WI 53705 USA

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 12期

基金：

美国国家科学基金会;

关键词：

allenes; catalysis; cycloaddition; enynes; rhodium; NATURAL-PRODUCT SYNTHESIS; DIELS-ALDER REACTION; 7-MEMBERED RINGS; MECHANISTIC ASPECTS; VINYL AZIRIDINES; ALKYNES; METAL; VINYLCYCLOPROPANES; CHIRALITY; 4C+3C;

D O I：

10.1002/adsc.201600196

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We recently developed a completely new type of Rh-catalyzed [5+2] cycloaddition by using 3-acyloxy-1,4-enyne (ACE) as the 5-carbon building block. In this update, we show that ACE can undergo intramolecular [5+2] cycloaddition with either an alkene or an allene in the presence of an appropriate rhodium catalyst and ligands to afford bicyclic compounds with multiple stereogenic centers. In most cases, cis-fused bicyclo[5.3.0]decadienes are prepared highly diastereoselectively.

引用

页码：2007 / 2011

页数：5

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