| 有机催化异氰基乙酸甲酯与芳香醛亚胺的不对称Mannich反应 |
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| 引用本文： | 王黎明,穆宏文,卢栋泽,李雪涛,李彤,金瑛.有机催化异氰基乙酸甲酯与芳香醛亚胺的不对称Mannich反应[J].应用化学,2019,36(7):758-763. |
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| 作者姓名： | 王黎明 穆宏文 卢栋泽 李雪涛 李彤 金瑛 |
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| 作者单位： | 吉林医药学院药学院 吉林 吉林132013 |
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| 基金项目： | 国家自然科学基金(21102055)、吉林省科技厅自然科学基金项目(20190201077JC)、吉林省卫生厅创新项目(2017J104)和吉林省大学生创新创业训练计划项目(201817)资助项目 |
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| 摘 要： | 将金鸡纳生物碱衍生物用于有机催化异氰基乙酸甲酯与芳香醛亚胺的不对称Mannich反应。考察溶剂、温度及催化剂用量对反应催化性能的影响。结果表明,最佳催化条件为摩尔分数10%催化剂1b,甲苯为溶剂,4A型分子筛,室温反应。产物产率为55%~80%,对映选择性最高达82%ee(对映体过量值)和非对映选择性(dr)达到>99∶1。
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| 关 键 词： | 金鸡纳生物碱衍生物 有机催化 不对称Mannich反应 异氰基乙酸甲酯 |
| 收稿时间： | 2018-10-29 |
Organocatalyzed Asymmetric Mannich Reaction of Isocyanoacetate with Tosylimines |
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| WANG Liming,MU Hongwen,LU Dongze,LI Xuetao,LI Tong,JIN Ying.Organocatalyzed Asymmetric Mannich Reaction of Isocyanoacetate with Tosylimines[J].Chinese Journal of Applied Chemistry,2019,36(7):758-763. |
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| Authors: | WANG Liming MU Hongwen LU Dongze LI Xuetao LI Tong JIN Ying |
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| Institution: | Department of Pharmacy,Jilin Medical University,Jilin,Jilin 132013,China |
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| Abstract: | Cinchona alkaloid derivatives as organocatalysts were applied in asymmetric Mannich reaction of isocyanoacetate with N-tosyl aryl aldimines. The effect of solvent, temperature and catalyst loading ammount were investigated. The optimized conditions were confirmed to include toluene as the solvent with a molar fraction 10% loading of catalyst 1b at room temperature. The desired products were obtained in 55%~80% yield with high diastereo- and enantioselectivities(trans/cis up to >99：1 and 82%ee). |
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| Keywords: | cinchona alkaloid derivatives organocatalysis asymmetric mannich reaction isocyanoacetate |
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