Copper(I)‐Catalyzed Asymmetric Dearomatization of Indole Acetamides with 3‐Indolylphenyliodonium Salts |
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| Authors: | Dr. Chuan Liu Ji‐Cheng Yi Xiao‐Wei Liang Ren‐Qi Xu Prof. Li‐Xin Dai Prof. Dr. Shu‐Li You |
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| Affiliation: | 1. http://shuliyou.sioc.ac.cn;2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, P. R. China;3. Collaborative Innovation Centre of Chemical Science and Engineering, Tianjin, P. R. China |
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| Abstract: | The rapid and direct asymmetric synthesis of 3‐(3a‐indolyl)hexahydropyrroloindoline motifs is an extremely important part of the total synthesis of several alkaloid structures. Herein, an intermolecular, asymmetric cascade dearomatization reaction of indole acetamides with 3‐indolylphenyliodonium salts has been developed. This protocol provides a straightforward access to 3‐(3a‐indolyl)hexahydropyrroloindolines bearing an all‐carbon quaternary stereocenter at the C3 position of the indoline ring with high enantioselectivities. The utility of the protocol has been demonstrated by the formal asymmetric synthesis of folicanthine. |
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| Keywords: | asymmetric catalysis dearomatization indole iodonium salts natural products |
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