手性叔胺脲催化靛红亚胺与苯胺的不对称aza-Mannich反应  

Chiral tertiary amine urea catalyzed enantioselective sza-Mannich reaction of isatin ketimines and aryl amines

作　　者：姜惠婷 李昕潞 金言 王黎明 金瑛 JIANG Hui-ting;LI Xin-lu;JIN Yan;WANG Li-ming;JIN Ying(Department of Pharmacy,Jilin Medical University,Jilin 132013,China;College of Science,Yanbian University,Yanji 133000,China)

机构地区：[1]吉林医药学院药学院,吉林吉林132013 [2]延边大学理学院,吉林延吉133000

出　　处：《化学研究与应用》2023年第3期640-644,共5页Chemical Research and Application

基　　金：吉林省科技厅科学技术项目(YDZJ202201ZYTS552)资助;国家级大学生创新创业训练计划项目(202113706009)资助。

摘　　要：报道了Takemoto型手性(硫)脲催化靛红亚胺与苯胺的不对称aza-Mannich反应。在0.1 mmol反应量下,筛选出最佳催化剂体系为:10 mol%催化剂N-[3,5-二(三氟甲基)苯基]-N′-[(1S,2S)-2-(二甲氨基)环己基]脲1d,1 mL乙醚,0℃反应。以71~82%的收率和最高达97%ee获得系列手性3-N,N′-靛红缩酮。Takemoto􀆳s(thio)urea derivatives were applied in the asymmetric aza-Mannich reaction of isatin ketimines and aryl amines.Under 0.1 mmol ammount,the optimal conditions were screened to be 10 mol%loading catalyst N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(1S,2S)-2-(dimethylamino)cyclohexyl]urea 1d in Et_(2)O(1 mL)at 0℃.Different substrates were evaluated for the generality of this reaction,and the desired chiral 3-N,N′-ketal isatins were obtained in 71~82%yields with up to 97%enantiomeric excess(ee).

关 键 词：Takemoto型(硫)脲衍生物 不对称催化 aza-Mannich反应 手性缩酮 靛红亚胺 

分 类 号：O621.3[理学—有机化学]