Synthesis of Substituted Pyrroles via Copper‐Catalyzed Cyclization of Ethyl Allenoates with Activated Isocyanides |
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| Authors: | Prof. Kui Lu Fang Ding Long Qin Xiaoliang Jia Chuanming Xu Prof. Xia Zhao Dr. Qingwei Yao Prof. Peng Yu |
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| Affiliation: | 1. China International Science and Technology Cooperation Base of Food Nutrition/Safety and Medicinal Chemistry, Sino-French Joint Lab of Food Nutrition/Safety and Medicinal Chemistry, Key Laboratory of Industrial Microbiology of Ministry of Education, Tianjin Key Laboratory of Industry Microbiology, College of Biotechnology, Tianjin University of Science & Technology, Tianjin, China;2. College of Chemistry, Tianjin Normal University, Tianjin, China;3. Sphinx Scientific Laboratory Corporation, Cody, Wyoming, USA |
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| Abstract: | A new method for the synthesis of di‐ and trisubstituted pyrroles via copper‐catalyzed cyclization of ethyl allenoates with activated isocyanides has been developed. In contrast to related annulation reactions previously reported, this new process features a skeletal rearrangement in which the aryl sulfonyl moiety, which functions as the electron‐withdrawing group in the α‐carbon of the isocyanide, was found to migrate to the γ‐carbon of the starting allenoate in the final product for the first time. |
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| Keywords: | allenoates copper cyclization isocyanides pyrrole synthesis |
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