有机催化靛红亚胺与1,2,4-三氮唑衍生物的不对称aza-Mannich反应  

Organocatalyzed Enantioselective Aza-Mannich Reaction of Isatinderived Ketimines and 1,2,4-Triazoles

作　　者：姜惠婷 顾盈盈 孙玉虹 王黎明 金瑛 JIANG Hui-ting;GU Ying-ying;SUN Yu-hong;WANG Li-ming;JIN Ying(Department of Pharmacy,Jilin Medical University,Jilin132013,China;Department of Pharmacy,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]延边大学药学院,吉林延吉133000

出　　处：《分子催化》2023年第5期484-491,I0003,共9页Journal of Molecular Catalysis(China)

基　　金：吉林省科技厅自然科学基金项目(No.20230101226JC);国家级大学生创新创业训练计划项目(No.S202213706012)资助。

摘　　要：将Takemoto型(硫)脲衍生物用于催化靛红亚胺与1,2,4-三氮唑的不对称aza-Mannich反应.筛选出最佳催化剂体系为:10%(摩尔分数)的1-[3,5-双(三氟甲基)苯基]-3-[(1R,2R)-2-(吡咯烷-1-基)环己基]硫脲催化剂1e,1 mL乙醚为溶剂,室温反应.以77%~90%的产率和最高达99%的对映选择性获得手性3-N,N’-缩酮-2-吲哚酮衍生物.Takemoto′s(thio)urea derivatives were applied in the asymmetric aza-Mannich reaction of isatin derived ketimines and 1,2,4-triazoles.The screened optimal conditions were determined to be 10%(Mole fraction)loading catalyst(R,R)-N-pyrrole thiourea 1e in Et2O(1 mL)at rt.The different substituted substrates were evaluated for the generality of this reaction,the desired chiral 3,3-diamino-2-oxindoles bearing N,N’-ketal structural motif were obtained in 77%~90%yields with up to 99%enantiomeric excess(ee).

关 键 词：Takemoto型(硫)脲衍生物 不对称aza-Mannich反应 靛红亚胺 1 2 4-三氮唑 

分 类 号：O643[理学—物理化学]