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
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
收藏
页码:2007 / 2011
页数:5
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