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A convenient method for synthesis of polyfunctional dihydropyrrole spiro-fused oxindole-2-ones via an organocatalytic tandem Michael/cyclization sequence
Affiliation:1. Guizhou Engineering Center for Innovative Traditional Chinese Medicine and Ethnic Medicine, College of Pharmacy, Guizhou University, Guiyang 550025, China;2. Key Laboratory for Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;1. State Key Laboratory of Biotherapy, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, China;2. Analytical & Testing Center, Sichuan University, Chengdu 610064, China;1. Guizhou Engineering Center for Innovative Traditional Chinese Medicine and Ethnic Medicine, College of Pharmacy, Guizhou University, Guiyang 550025, Guizhou, PR China;2. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan, PR China;1. Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;2. University of Chinese Academy of Sciences, Beijing, China;1. National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;2. School of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000, China;3. University of Chinese Academy of Sciences, Beijing 100049, China;1. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;2. Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu 610041, China;3. University of Chinese Academy of Sciences, Beijing 100049, China
Abstract:A new methodology was developed for the synthesis of spirocyclic oxindoles bearing polyfunctional dihydropyrrole units via an organocatalytic tandem Michael/cyclization sequence. Products bearing adjacent quaternary–tertiary stereocenters were smoothly obtained in high yields (up to 97% yield) with excellent diastereoselectivities up to >20/1.
Keywords:Spirocyclic oxindoles  Dihydropyrrole  Quaternary–tertiary stereocenters  Michael/cyclization  Organocatalysis
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