Stereoselective Synthesis of Hydropyrano[3,2-b]indoles via Organocatalytic Asymmetric Inverse-Electron-Demand Oxa-Diels-Alder Reaction

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• 作者：Lei Yang ; Wei Huang ; Xiang-Hong He ; Ming-Cheng Yang ; Xiang Li ; Gu He ; Cheng Peng and Bo Han
• 刊名：Advanced Synthesis & Catalysis
• 出版年：2016
• 出版时间：September 15, 2016
• 年：2016
• 卷：358
• 期：18
• 页码：2970-2975
• 全文大小：966K
• ISSN：1615-4169

文摘

Enantio- and diastereoselective inverse-electron-demand oxa-Diels–Alder reactions are described between (Z)-2-ylideneoxindoles and aldehydes in the presence of a chiral secondary amine catalyst. The corresponding hydropyrano[3,2-b]indoles are produced in up to 77% yield with up to 99% ee. Convenient synthetic transformations of the products readily lead to pharmacologically interesting scaffolds bearing multiple functional groups. This method may also provide an alternative approach for the asymmetric synthesis of 2-spirocyclo-3-oxindoles.