Construction of Novel Tetrahydro-β-carboline-1-thione Spirooxindoles by Brønsted Acid Mediated Formal [3+3] Cyclization of 3-Indolylmethanols with 3-Isothiocyanato Oxindoles
Yijun Liao
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorMei Bai
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorShuowen Yu
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorMinmin Zhang
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorFangzhi Hu
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorXiaoying Xu
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
Search for more papers by this authorWeicheng Yuan
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
Search for more papers by this authorCorresponding Author
Xiaomei Zhang
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
E-mail: [email protected]Search for more papers by this authorYijun Liao
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorMei Bai
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorShuowen Yu
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorMinmin Zhang
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorFangzhi Hu
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorXiaoying Xu
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
Search for more papers by this authorWeicheng Yuan
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
Search for more papers by this authorCorresponding Author
Xiaomei Zhang
Key Laboratory for Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041 China
E-mail: [email protected]Search for more papers by this authorAbstract
p-Toluenesulfonic acid mediated formal [3+3] cyclization of 3-indolylmethanols with 3-isothiocyanato oxindoles was realized. This transformation allowed for the synthesis of a series of novel tetrahydro-β-carboline-1-thione spirooxindoles in moderate to excellent yields (up to 99%) with generally good diastereoselectivities (up to >20:1). The structure of one product was determined by an X-ray crystal structural analysis.
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References and Notes
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