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2024 , Vol. 44 >Issue 9: 2796 - 2809

DOI: https://doi.org/10.6023/cjoc202403039

研究论文

溶剂控制三氟甲烷磺酸钪催化2-(杂)芳基-N-磺酰基吖丁啶开环反应: 烯丙胺/1,3-噁嗪衍生物的合成

  • 朱洁 ,
  • 汤思丹 ,
  • 阚秀妹 ,
  • 凡士柱 ,
  • 王鹏飞 ,
  • 杨培俊
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  • a 安徽工程大学化学与环境工程学院 功能配合物材料化学与应用安徽省重点实验室 安徽芜湖 241000
    b 安徽师范大学化学与材料科学学院 分子基材料省级实验室 安徽芜湖 241002

收稿日期: 2024-03-26

  修回日期: 2024-05-14

  网络出版日期: 2024-05-30

基金资助

国家自然科学基金(22001007); 安徽工程大学科研基金(2020YQQ025); 安徽省重点分子基材料省级实验室开放基金(fzj22012)

收起

Solvent-Controlled Sc(OTf)3-Catalyzed Ring Opening Reaction of 2-(Hetero)aryl-N-sulfonylazetidines: Synthesis of Allylic Amines/1,3-Oxazinane Derivatives

  • Jie Zhu ,
  • Sidan Tang ,
  • Xiumei Kan ,
  • Shizhu Fan ,
  • Pengfei Wang ,
  • Peijun Yang
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  • a Anhui Province Key Laboratory of Functional Coordinated Complexes for Materials Chemistry and Application, School of Chemical and Environmental Engineering, Anhui Polytechnic University, Wuhu, Anhui 241000
    b Anhui Laboratory of Molecular-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241002
*E-mail:

Received date: 2024-03-26

  Revised date: 2024-05-14

  Online published: 2024-05-30

Supported by

National Natural Science Foundation of China(22001007); Anhui Engineering University Scientific Research Foundation(2020YQQ025); Anhui Laboratory Molecular-Based Materials Open Fund(fzj22012)

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摘要

烯丙胺和1,3-噁嗪烷是有机合成和医药工业中有重要价值的分子骨架. 报道了一种通过溶剂控制稀土金属路易斯酸催化2-(杂)芳基-N-磺酰基吖丁啶与醛环加成合成1,3-噁嗪烷以及自身开环异构化合成烯丙胺. 这两种反应具有底物适用范围广、催化剂用量低、反应条件温和、产率高和区域选择性好等特点, 并通过将产物三步转化为萘替酚、阿拉明和阿拉明SG证明了其实用价值.

关键词： 稀土金属路易斯酸; 溶剂控制; 吖丁啶; 区域选择性; 开环反应

本文引用格式

朱洁 , 汤思丹 , 阚秀妹 , 凡士柱 , 王鹏飞 , 杨培俊 . 溶剂控制三氟甲烷磺酸钪催化2-(杂)芳基-N-磺酰基吖丁啶开环反应: 烯丙胺/1,3-噁嗪衍生物的合成[J]. 有机化学, 2024 , 44(9) : 2796 -2809 . DOI: 10.6023/cjoc202403039

Abstract

Allylic amines and 1,3-oxazinanes are valuable molecular skeletons in organic synthesis and pharmaceutical industry. A straightforward way to such two types of compounds by solvent-controlled rare-earth metal Lewis acid-catalyzed transformations of 2-(hetero)aryl-N-sulfonylazetidines: the ring-opening isomerization of azetidines to allylic amines and the annulation of azetidines with aldehydes to 1,3-oxazinanes are reported. These two reactions feature scalability, low catalyst loading, mild reaction conditions, excellent yields and regioselectivity with demonstrated utility in three-step product transformations to naftifine, abamine and abamine SG.

Key words： rare-earth metal Lewis acid; solvent control; azetidine; regioselectivity; ring opening reaction

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