A general synthetic route to differentially functionalized angularly and linearly fused [6-7-5] ring systems: A Rh(I)-catalyzed cyclocarbonylation reaction

被引：31
|
作者：
Brummond, Kay A. [1 ]
Chen, Daitao [1 ]
Davis, Matthew A. [1 ]
机构：
[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 13期
关键词：
D O I：
10.1021/jo8007258
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Investigations of a Rh(I)-catalyzed cyclocarbonylation reaction reveal its general synthetic utility for accessing highly functionalized tricyclic [6-7-5] linear and angular ring systems from allene-ynes. Three types of allene-ynes were prepared and subjected to Rh(I)-catalyzed cyclocarbonylation conditions. For three series of allene-ynes, the [6-7-5] ring systems were afforded in varying yields depending on the substrate structure. One series of allene-ynes afforded the [6-6-5] ring system possessing an alpha-alkylidene cyclopentenone as a result of a selective reaction with the proximal double bond of the allene.
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收藏
页码：5064 / 5068
页数：5
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