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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.
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页码:2007 / 2011
页数:5
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