新型手性4 -吡咯烷基吡啶路易斯碱催化剂的合成  

Synthesis of Novel Chiral 4-Pyrrolidinopyridine Lewis Base Catalysts

作　　者：罗青青 唐雪 詹固 韩波[1] LUO Qingqing;TANG Xue;ZHAN Gu;HAN Bo(State Key Laboratory of Southwestern Chinese Medicine Resources,School of Pharmacy,Chengdu University of Traditional Chinese Medicine,Chengdu 611137,China)

机构地区：[1]成都中医药大学药学院、西南特色中药资源国家重点实验室,四川成都611137

出　　处：《合成化学》2023年第4期304-309,共6页Chinese Journal of Synthetic Chemistry

基　　金：四川省科技厅科技项目(2021YJ0402,2019YJ0321)。

摘　　要：以4-氯烟酸、 α , α -二芳基脯氨醇为原料,合成了5个新型手性4-吡咯烷基吡啶路易斯碱催化剂,分离收率60%~82%,其结构经 1 H NMR, 13 C NMR和HR-MS(ESI)表征。催化剂 5a 成功应用到茚三酮衍生的MBH碳酸酯与靛红衍生的缺电子烯烃的[3+2]环加成反应中,以良好的收率和立体选择性获得茚二酮-靛红双螺环 化合物 。Five novel chiral 4-pyrrolidinopyridine Lewis base catalysts were assembled in three steps from 4-chloronicotinic acid andα,α-diarylprolinol.The isolated yield was 60%~82%,and the structure was characterized by 1 H NMR,13 C NMR and HR-MS(ESI).Catalyst 5a was successfully applied to the[3+2]cycloaddition reaction of ninhydrin-derived MBH carbonate with isatin-derived electron-deficient olefins,affording bis-spiro compound in good yield with excellent stereoselectivity.

关 键 词：不对称催化 有机小分子 路易斯碱 4-吡咯烷基吡啶 合成 立体选择性 

分 类 号：O621.3[理学—有机化学]