吡啶并[1,2 - ] - 1 - 吲哚衍生物的不对称构建：金催化的环异构化反应
Asymmetric construction of pyrido[1,2-]-1-indole derivatives a gold-catalyzed cycloisomerization.
作者信息
Jiang Feng, Fu Chunling, Ma Shengming
机构信息
Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University Hangzhou 310027 Zhejiang People's Republic of China
出版信息
Chem Sci. 2020 Oct 22;12(2):696-701. doi: 10.1039/d0sc05619g.
Pyrido[1,2-]-1-indoles are important scaffolds found in many biologically active compounds. Herein, we first developed an IPrAuCl/AgSbF-catalyzed cycloisomerization of -1,3-disubstituted allenyl indoles affording pyrido[1,2-]-1-indoles. Then the axial-to-central chirality transfer starting from enantio-enriched -1,3-disubstituted allenylindoles affording optically active pyrido[1,2-]-1-indoles has been realized in excellent yields and enantioselectivities. A mechanism has been proposed based on mechanistic studies. Synthetic applications have also been demonstrated.
吡啶并[1,2 - ] - 1 - 吲哚是许多生物活性化合物中存在的重要骨架。在此，我们首次开发了一种IPrAuCl/AgSbF催化的1,3 - 二取代烯丙基吲哚的环异构化反应，得到吡啶并[1,2 - ] - 1 - 吲哚。然后，从对映体富集的1,3 - 二取代烯丙基吲哚出发，实现了轴向到中心的手性转移，以优异的产率和对映选择性得到光学活性的吡啶并[1,2 - ] - 1 - 吲哚。基于机理研究提出了一种机理。还展示了其合成应用。
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