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2023 , Vol. 43 >Issue 12: 4284 - 4293

DOI: https://doi.org/10.6023/cjoc202304020

研究论文

可见光催化N-芳基乙醛酸亚胺脱羧烷基化合成非天然氨基酸衍生物

  • 王永玲 ,
  • 张铁欣 ,
  • 张栩铭 ,
  • 孙晗扬 ,
  • 冷津瑶 ,
  • 李亚明
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  • 大连理工大学化工学院 精细化工国家重点实验室 大连 116024

收稿日期: 2023-04-17

  修回日期: 2023-06-16

  网络出版日期: 2023-07-13

基金资助

国家自然科学基金(22078045); 国家自然科学基金(21176039)

收起

Synthesis of Unnatural Amino Acid Derivatives by Visible- Light-Catalyzed Decarboxylative Alkylation of N-Aromatic Glyoxylimines

  • Yongling Wang ,
  • Tiexin Zhang ,
  • Xuming Zhang ,
  • Hanyang Sun ,
  • Jinyao Leng ,
  • Yaming Li
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  • State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024
*

Received date: 2023-04-17

  Revised date: 2023-06-16

  Online published: 2023-07-13

Supported by

National Natural Science Foundation of China(22078045); National Natural Science Foundation of China(21176039)

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摘要

研究了可见光诱导乙醛酸亚胺的脱羧自由基烷基化反应制备α-烷基化的非天然氨基酸衍生物. 四氯-N-羟基邻苯二甲酰亚胺(TCNHPI)活性酯在可见光照射下产生的多种烷基自由基以良好的收率与亚胺加成. 金属铱配合物为光催化剂, 汉斯酯(HE)为必不可少的氢转移试剂, 氟硼酸(HBF4)作为添加剂可显著提高产率. 反应条件温和, 显示了广泛的底物适用范围. 此外, 简单有效的一锅合成法, 包括乙醛酸乙酯、伯胺和TCNHPI活性酯的多组分反应也能够顺利进行, 该方案为α-烷基化的非天然氨基酸衍生物的合成提供了一种新的方法.

关键词： 光催化; N-芳基乙醛酸亚胺; 脱羧; 一锅法; 非天然氨基酸衍生物

本文引用格式

王永玲 , 张铁欣 , 张栩铭 , 孙晗扬 , 冷津瑶 , 李亚明 . 可见光催化N-芳基乙醛酸亚胺脱羧烷基化合成非天然氨基酸衍生物[J]. 有机化学, 2023 , 43(12) : 4284 -4293 . DOI: 10.6023/cjoc202304020

Abstract

A visible-light-mediated decarboxylative radical alkylation of glyoxylimines for preparing α-alkylated unnatural amino acid derivatives was developed. Various alkyl radicals generated by tetrachloro-N-hydroxyphthalimide (TCNHPI) active esters were added to imines in good yields under visible light irradiation. Iridium complex was selected as photocatalyst and also, Hantzsch ester (HE) as hydrogen transfer reagent was essential. Fluoboric acid (HBF4) significantly improved the yield. Mild reaction conditions showed wide substrate scopes. In addition, the straightforward and efficient one-pot procotol, involved a multicomponent reaction of ethyl glyoxalate, primary amine and TCNHPI active ester occurred smoothly. This scheme provides a new method for the synthesis of α-alkylated unnatural amino acid derivatives.

Key words： photocatalysis; N-aromatic glyoxylimines; decarboxylation; one-pot; unnatural amino acid derivatives

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