Efficient cyclotrimerization of bicyclic vic-bromostannylalkenes promoted by copper(I) thiophen-2-carboxylate

被引：38
作者：
Borsato, G
De Lucchi, O
Fabris, F
Groppo, L
Lucchini, V
Zambon, A
机构：
[1] Univ Venice, Dipartimento Sci Ambientali, I-30123 Venice, Italy
[2] Univ Venice, Dipartimento Chim, I-30123 Venice, Italy
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 22期
关键词：
D O I：
10.1021/jo020396s
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Copper(I) thiophen-2-carboxylate was successfully employed in the trimerization of [2.2.1] bicyclic vic-bromotrimethyltin olefins (in their racemic composition), bearing different functionalities, to invariably obtain almost quantitative yields of the syn and anti tris-annelated benzenes. The two isomers come in different ratios, smaller than or equal to the statistical 1:3 ratio, depending on the steric hindrance opposed by the functionalities. In the case of enantiopure (3-bromo-4,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl)trimethylstannane, the 1:9 ratio found with Cu(NO3)(2).3H(2)O increases to 1:6.
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页码：7894 / 7897
页数：4
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