Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal[3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin |
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Authors: | Jian Li Qi-Long Hu Xue-Ping Chen Ke-Qiang Hou Albert S C Chan Xiao-Feng Xiong |
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Institution: | Guangdong Key Laboratory of Chiral Molecule and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China |
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Abstract: | An efficient asymmetric and enantio-swithchable organocatalytic3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to > 20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo-and enantioselectivity. |
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Keywords: | Organocatalysis Asymmetric synthesis Enantioswitchable Cinchona alkaloid Tetrahydropyran[3 2-c]quinolines |
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