Jiang Feng, Fu Chunling, Ma Shengming
Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University Hangzhou 310027 Zhejiang People's Republic of China
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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