Regio‐ and Enantioselective Aza‐Diels–Alder Reactions of 3‐Vinylindoles: A Concise Synthesis of the Antimalarial Spiroindolone NITD609 |
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| Authors: | Haifeng Zheng Prof?Dr Xiaohua Liu Chaoran Xu Yong Xia Dr Lili Lin Prof?Dr Xiaoming Feng |
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| Institution: | 1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064 (China);2. Collaborative Innovation Center of Chemical Science and Engineering Tianjin (China) |
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| Abstract: | An asymmetric aza‐Diels–Alder reaction of 3‐vinylindoles with isatin‐derived ketimines has been developed. A series of spiroindolone derivatives were thus obtained in good to excellent yields with excellent enantioselectivity (up to 96 % yield and 99 % ee). Furthermore, the antimalarial compound NITD609 could be obtained in three steps with an overall yield of 40.6 %. Control experiments and operando IR experiments imply a concerted reaction pathway. The regioselectivity and exo selectivity result from π–π interactions between the two indoline rings of the two reactants. |
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| Keywords: | asymmetric catalysis aza‐Diels– Alder reactions indoles ketimines nickel catalysis |
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