An exploratory study of type II [3+4] cycloadditions between vinylcarbenoids and dienes

被引：54

作者：

Davies, HML ^{[1
]}

Calvo, RL ^{[1
]}

Townsend, RJ ^{[1
]}

Ren, PD ^{[1
]}

Churchill, RM ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 14期

关键词：

D O I：

10.1021/jo991959b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular type II [3 + 4] cycloaddition between vinylcarbenoids and furans is a practical method for the construction of 5-oxo-10-oxatricyclo[6.2.1.0(4.9)]undeca-3,8(11)-dienes, containing two anti-Bredt double bonds. These tricyclic systems are well functionalized for eventual elaboration to the natural product CP-263,114. The rhodium-stabilized vinylcarbenoids are generated by dirhodium tetracarboxylate catalyzed decomposition of vinyldiazoacetates. The [3 + 4] cycloaddition is generally considered to occur by a tandem cyclopropanation/Cope rearrangement, although evidence is presented that with these substrates the [3 + 4] cycloaddition may occur in a concerted manner.

引用

页码：4261 / 4268

页数：8

共 39 条

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