Asymmetric Double Michael Reaction Catalyzed by Simple Primary Amine Catalysts: A Straightforward Approach to Construct Spirocyclic Oxindoles
Xiya Luo
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Graduate University of Chinese Academy of Sciences, Beijing 10039, China
Search for more papers by this authorLiangliang Wang
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Graduate University of Chinese Academy of Sciences, Beijing 10039, China
Search for more papers by this authorLin Peng
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorJianfei Bai
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Graduate University of Chinese Academy of Sciences, Beijing 10039, China
Search for more papers by this authorLina Jia
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Graduate University of Chinese Academy of Sciences, Beijing 10039, China
Search for more papers by this authorGuangyun He
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorFang Tian
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorCorresponding Author
Xiaoying Xu
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China, Tel.: 0086-028-85255208; Fax: 0086-028-85255208Search for more papers by this authorCorresponding Author
Lixin Wang
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China, Tel.: 0086-028-85255208; Fax: 0086-028-85255208Search for more papers by this authorXiya Luo
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Graduate University of Chinese Academy of Sciences, Beijing 10039, China
Search for more papers by this authorLiangliang Wang
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Graduate University of Chinese Academy of Sciences, Beijing 10039, China
Search for more papers by this authorLin Peng
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorJianfei Bai
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Graduate University of Chinese Academy of Sciences, Beijing 10039, China
Search for more papers by this authorLina Jia
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Graduate University of Chinese Academy of Sciences, Beijing 10039, China
Search for more papers by this authorGuangyun He
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorFang Tian
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Search for more papers by this authorCorresponding Author
Xiaoying Xu
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China, Tel.: 0086-028-85255208; Fax: 0086-028-85255208Search for more papers by this authorCorresponding Author
Lixin Wang
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, Sichuan 610041, China, Tel.: 0086-028-85255208; Fax: 0086-028-85255208Search for more papers by this authorAbstract
The enantioselective double Michael reaction of N-Boc-3-nonsubstitued oxindoles with dienones catalyzed by chiral monoimide protected cyclohexane-1,2-diamines was developed. A wide range of optically active spirocyclic oxindoles were obtained up to 98% yield and up to 89% ee.
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- 19 General procedure for double Michael reaction of N-Boc-3-nonsubstitued oxindoles with dienones: To a stirred solution of catalyst (20 mol%) and dienones (0.2 mmol) in toluene (1.0 mL) was added oxindoles (2.0 equiv.) at −30°C for 96 h. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate) to give the desired product. The ee value was determined by HPLC analyses (for 4a–4d, 4g–4l, 4n and 4o, HPLC condition: AD-H, 1.0 mL/min, V(hexane):V(i-PrOH) =90:10; for 4e, HPLC condition: AD-H, 1.0 mL/min, V(hexane):V(i-PrOH)=97:3; for 4f, HPLC condition: AS-H, 1.0 mL/min, V(hexane):V(i-PrOH)=80:20; for 4m, HPLC condition: IC-H, 1.0 mL/min, V(hexane):V(i-PrOH)=95:5).
