Synthesis of Vinylcycloheptadienes by the Nickel-Catalyzed Three-Component [3+2+2] Cocyclization. Application to the Synthesis of Polycyclic Compounds

被引：35

作者：

Komagawa, Shinsuke ^{[1
]}

Takeuchi, Kouhei ^{[1
]}

Sotome, Ikuo ^{[1
]}

Azumaya, Isao ^{[2
]}

Masu, Hyuma ^{[2
]}

Yamasaki, Ryu ^{[1
]}

Saito, Shinichi ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Sci, Dept Chem, Shinjuku Ku, Tokyo 1628601, Japan

[2] Tokushima Bunri Univ, Fac Pharmaceut Sci, Kagawa 7692193, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 09期

关键词：

DIELS-ALDER REACTIONS; AVAILABLE STARTING MATERIALS; FISCHER CARBENE COMPLEXES; CYCLOADDITION REACTIONS; ETHYL CYCLOPROPYLIDENEACETATE; 7-MEMBERED RINGS; CONJUGATED ENYNES; REGIOSELECTIVE CYCLOTRIMERIZATION; MULTICOMPONENT REACTIONS; CYCLIZATION REACTIONS;

D O I：

10.1021/jo900189g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The nickel-catalyzed [3 + 2 + 2] cycloaddition of ethyl cyclopropylideneacetate and conjugated enynes proceeded smoothly and divinylcycloheptadienes were isolated in high yields. The three-component cocyclization of ethyl cyclopropylideneacetate, conjugated enynes, and (trimethylsilyl)acetylene also proceeded in a highly selective manner to afford vinylcycloheptadienes, which were reacted with various dienophiles. This study provided a new, short-step synthesis of polycyclic compounds with cycloheptane skeleton.

引用

页码：3323 / 3329

页数：7

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