Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes.
Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes.
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DOI：
10.1021/acs.orglett.9b00594
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发表时间：
2019-03
期刊：
影响因子：
5.2
通讯作者：
Logan A. Combee;Shea L. Johnson;Julie E Laudenschlager;Michael K. Hilinski
中科院分区：
文献类型：
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作者：
Logan A. Combee;Shea L. Johnson;Julie E Laudenschlager;Michael K. Hilinski
报道了芳基取代的乙烯基环丙烷与类硝基前体之间的形式[5+1]环加成反应。该方法使用Rh2(Esp)2作为催化剂，导致了取代四氢吡啶的高度区域选择性的形成。初步的机理研究支持一种由先前观察到的Rh-硝基的Lewis酸性所实现的逐步的、极性的机理。总体而言，这项工作扩大了氮烯转移环加成反应的应用，这是一种相对未被探索的杂环合成方法，用于形成六元环。
Formal [5 + 1] cycloadditions between aryl-substituted vinylcyclopropanes and nitrenoid precursors are reported. The method, which employs Rh2(esp)2 as a catalyst, leads to the highly regioselective formation of substituted tetrahydropyridines. Preliminary mechanistic studies support a stepwise, polar mechanism enabled by the previously observed Lewis acidity of Rh-nitrenoids. Overall, this work expands the application of nitrene-transfer cycloaddition, a relatively underexplored approach to heterocycle synthesis, to the formation of six-membered rings.