| 姜惠婷,顾盈盈,孙玉虹,王黎明,金瑛.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[J].分子催化,2023,37(5):484-491 |
| 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 Isatin-derived Ketimines and 1,2,4-Triazoles |
| 投稿时间：2023-05-23 修订日期：2023-06-20 |
| DOI：10.16084/j.issn1001-3555.2023.05.007 |
| 中文关键词: Takemoto型(硫)脲衍生物 不对称aza-Mannich反应 靛红亚胺 1,2,4-三氮唑 |
| 英文关键词:Takemoto's (thio)urea derivatives asymmetric aza-Mannich reaction isatin derived ketimines 1,2,4-triazoles |
| 基金项目: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 |
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| 中文摘要: |
| 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. |
| 英文摘要: |
| 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). |
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