Asymmetric construction of pyrido[1,2-a]-1H-indole derivatives via a gold-catalyzed cycloisomerization |
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| Authors: | Feng Jiang Chunling Fu Shengming Ma |
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| Institution: | Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027 Zhejiang People''s Republic of China, |
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| Abstract: | Pyrido1,2-a]-1H-indoles are important scaffolds found in many biologically active compounds. Herein, we first developed an IPrAuCl/AgSbF6-catalyzed cycloisomerization of N-1,3-disubstituted allenyl indoles affording pyrido1,2-a]-1H-indoles. Then the axial-to-central chirality transfer starting from enantio-enriched N-1,3-disubstituted allenylindoles affording optically active pyrido1,2-a]-1H-indoles has been realized in excellent yields and enantioselectivities. A mechanism has been proposed based on mechanistic studies. Synthetic applications have also been demonstrated.We reported an IPrAuCl/AgSbF6-catalyzed cycloisomerization of enantio-enriched N-1,3-disubstituted allenylindoles affording optically active pyrido1,2-a]-1H-indoles in excellent yields and enantioselectivities. |
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