有机催化异氰基乙酸甲酯与芳香醛亚胺的不对称Mannich反应

doi:10.11944/j.issn.1000-0518.2019.07.180340

摘要/Abstract

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。

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

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).

Key words: cinchona alkaloid derivatives, organocatalysis, asymmetric mannich reaction, isocyanoacetate

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.

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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