Catalytic Asymmetric Synthesis of [2,3]-Fused Indoline Heterocycles through Inverse-Electron-Demand Aza-Diels–Alder Reaction of Indoles with Azoalkenes†
Min-Chao Tong
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (China)
Search for more papers by this authorXuan Chen
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (China)
Search for more papers by this authorJun Li
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (China)
Search for more papers by this authorRong Huang
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (China)
Search for more papers by this authorHaiyan Tao
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Chun-Jiang Wang
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (China)
State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, 300071 (China)
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (China)===Search for more papers by this authorMin-Chao Tong
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (China)
Search for more papers by this authorXuan Chen
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (China)
Search for more papers by this authorJun Li
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (China)
Search for more papers by this authorRong Huang
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (China)
Search for more papers by this authorHaiyan Tao
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Chun-Jiang Wang
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (China)
State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, 300071 (China)
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 (China)===Search for more papers by this authorThis work was supported by the 973 Program (2011CB808600), NSFC (21172176, 21372180), and the Hubei Province NSF (ZRZ0273).
Abstract
An unprecedented catalytic asymmetric inverse-electron-demand aza-Diels–Alder reaction of indoles with in situ formed azoalkenes is reported. A diverse set of [2,3]-fused indoline heterocycles were achieved in generally good yields (up to 97 %) with high regioselectivity and diastereoselectivity (>20:1 d.r.), and with excellent enantioselectivity (up to 99 % ee).
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