张敏, 甘坤, 刘莉, 陈治明. 手性双硫脲催化不对称Pictet-Spengler环化反应[J]. 云南大学学报(自然科学版), 2022, 44(4): 812-821. doi: 10.7540/j.ynu.20210425
引用本文: 张敏, 甘坤, 刘莉, 陈治明. 手性双硫脲催化不对称Pictet-Spengler环化反应[J]. 云南大学学报(自然科学版), 2022, 44(4): 812-821. doi: 10.7540/j.ynu.20210425
ZHANG Min, GAN Kun, LIU Li, CHEN Zhi-ming. Asymmetric Pictet-Spengler cyclization reaction catalyzed by chiral thiourea[J]. Journal of Yunnan University: Natural Sciences Edition, 2022, 44(4): 812-821. DOI: 10.7540/j.ynu.20210425
Citation: ZHANG Min, GAN Kun, LIU Li, CHEN Zhi-ming. Asymmetric Pictet-Spengler cyclization reaction catalyzed by chiral thiourea[J]. Journal of Yunnan University: Natural Sciences Edition, 2022, 44(4): 812-821. DOI: 10.7540/j.ynu.20210425

手性双硫脲催化不对称Pictet-Spengler环化反应

Asymmetric Pictet-Spengler cyclization reaction catalyzed by chiral thiourea

  • 摘要: 合成了3种新颖具有轴手性多氢键多活性中心的双硫脲催化剂 (1a ~ 1c) ,并将其应用于催化Pictet-Spengler反应合成β-咔啉类化合物. 实验结果表明,在室温(25 ℃)下,甲苯为溶剂,催化剂 1c 的用量为x=20%,Pictet-Spengler环化反应取得较高的收率(82%)和较高的对映选择(88%).

     

    Abstract: In this paper, three dithiourea catalysts (1a ~ 1c) with axial chiral multiple hydrogen bonds and multiple active centers were synthesized and applied to catalyze the Pictet-Spengler reaction to synthesize β-carbolines. The experimental results showed that at room temperature (25 ℃), toluene is used as the solvent, the amount of catalyst 1c is x=20%, Pictet-Spengler cyclization reaction has achieved a higher yield (82%) and a higher enantiomer selectivity (88%).

     

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