金（I）催化的亚乙烯基环丙烷烯的环异构化反应——卡宾或非卡宾过程。
Gold(i)-catalyzed cycloisomerization of vinylidenecyclopropane-enes carbene or non-carbene processes.
作者信息
Li De-Yao, Wei Yin, Marek Ilan, Tang Xiang-Ying, Shi Min
机构信息
State Key Laboratory of Organometallic Chemistry , Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , P. R. China . Email:
Schulich Faculty of Chemistry , Technion-Israel Institute of Technology , Technion City , Haifa 32000 , Israel . Email:
出版信息
Chem Sci. 2015 Oct 1;6(10):5519-5525. doi: 10.1039/c5sc01806d. Epub 2015 Jun 24.
Gold catalyzed cycloisomerization of aromatic ring tethered vinylidenecyclopropane-enes provides a divergent synthetic protocol for the construction of O-containing fused heterocycles through controllable carbene or non-carbene related processes. The carbene induced process features a new amphiphilic strategy to generate a gold carbene a rearrangement of vinylidenecyclopropane. Whereas, the electronic effect of the -substituents switches the reaction mode onto the non-carbene related process, from which five- or six-membered rings are selectively produced through allyl-migration.
金催化芳环连接的亚乙烯基环丙烷类化合物的环异构化反应，通过可控的卡宾或非卡宾相关过程，为构建含氧化态稠合杂环提供了一种多样化的合成方法。卡宾诱导的过程具有一种新的两亲性策略，可生成金卡宾并引发亚乙烯基环丙烷的重排。然而，α-取代基的电子效应将反应模式转变为非卡宾相关过程，通过烯丙基迁移从中选择性地生成五元或六元环。
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