通过镍催化的三组分[3 + 2 + 2]共环化反应合成乙烯基环庚二烯。在多环化合物合成中的应用。
Synthesis of vinylcycloheptadienes by the nickel-catalyzed three-component [3 + 2 + 2] cocyclization. Application to the synthesis of polycyclic compounds.
作者信息
Komagawa Shinsuke, Takeuchi Kouhei, Sotome Ikuo, Azumaya Isao, Masu Hyuma, Yamasaki Ryu, Saito Shinichi
机构信息
Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601, Japan.
出版信息
J Org Chem. 2009 May 1;74(9):3323-9. doi: 10.1021/jo900189g.
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.
镍催化的环丙基乙酸乙酯与共轭烯炔的[3 + 2 + 2]环加成反应顺利进行，二乙烯基环庚二烯以高产率分离得到。环丙基乙酸乙酯、共轭烯炔和（三甲基硅基）乙炔的三组分共环化反应也以高度选择性的方式进行，得到乙烯基环庚二烯，其可与各种亲双烯体反应。该研究为具有环庚烷骨架的多环化合物提供了一种新的短步骤合成方法。
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