Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal[3+3]annulation of quinolinones and MBH 2-naphthoates of nitroolefin  

作　　者：Jian Li Qi-Long Hu Xue-Ping Chen Ke-Qiang Hou Albert S.C.Chan Xiao-Feng Xiong 

机构地区：[1]Guangdong Key Laboratory of Chiral Molecule and Drug Discovery,School of Pharmaceutical Sciences,Sun Yat-sen University,Guangzhou 510006,China

出　　处：《Chinese Chemical Letters》2020年第3期697-700,共4页中国化学快报（英文版）

基　　金：financial support from the National Natural Science Foundation of China(No.81602972);Guangdong Natural Science Funds for Distinguished Young Scholar(No.2018B030306017);Guangdong Province Universities and Colleges Pearl River Scholar Funded Scheme(2018)。

摘　　要：An efficient asymmetric and enantio-swithchable organocatalytic[3+3]annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed.Densely substituted tetrahydropyrano[3,2-c]qui noli nones 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.

关 键 词：Organocatalysis ASYMMETRIC synthesis Enantioswitchable CINCHONA alkaloid Tetrahydropyran[3 2-c]quinolines 

分 类 号：O626[理学—有机化学] TQ463.5[理学—化学]