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
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
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页码:3323 / 3329
页数:7
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