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2023 , Vol. 43 >Issue 4: 1472 - 1482

DOI: https://doi.org/10.6023/cjoc202209014

研究论文

2-芳甲酰基甲亚基丙二酸酯与Corey叶立德的反应

  • 陈文龙 ,
  • 李慧敏 ,
  • 杨鹏飞 ,
  • 郑东程 ,
  • 杨高升
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  • 安徽师范大学化学与材料科学学院 教育部功能化分子固体重点实验室分子基材料安徽省重点实验室 安徽芜湖 241002

收稿日期: 2022-09-12

  修回日期: 2022-11-14

  网络出版日期: 2022-12-12

基金资助

国家自然科学基金(21672005); 国家自然科学基金(21172002)

收起

Reaction of 2-Aroylmethylenemalonates with Corey Ylide

  • Wenlong Chen ,
  • Huimin Li ,
  • Pengfei Yang ,
  • Dongcheng Zheng ,
  • Gaosheng Yang
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  • MOE Key Laboratory of Functionalized Molecular Solids, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241002
* Corresponding author.

Received date: 2022-09-12

  Revised date: 2022-11-14

  Online published: 2022-12-12

Supported by

National Natural Science Foundation of China(21672005); National Natural Science Foundation of China(21172002)

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摘要

研究了2-芳甲酰基甲亚基丙二酸酯与Corey叶立德的反应. 1.0 equiv.的三甲基碘化亚砜与2.5 equiv.氢化钠在N,N-二甲基甲酰胺(DMF)溶剂中制得的Corey叶立德, 与2-芳甲酰甲亚基丙二酸酯在－23 ℃条件下通过亲核加成/消除过程得到2-(1-芳甲酰基乙烯基)丙二酸酯; 2.2 equiv.的三甲基碘化亚砜与5.0 equiv.氢化钠在DMF溶剂中制得的Corey叶立德, 与2-芳甲酰甲亚基丙二酸酯在－23~0 ℃条件下通过亲核加成/消除/加成/环丙烷化过程得到2-(1-芳甲酰基环丙基)丙二酸酯; 1.1 equiv.的三甲基碘化亚砜与5.0 equiv.碳酸钾在DMF溶剂中制得的Corey叶立德, 与2-芳甲酰甲亚基丙二酸酯在0 ℃条件下通过亲核加成/环丙烷化过程得到2-芳甲酰基-1,1-环丙烷二羧酸酯. 这三种过程可以通过简单调节碱及其用量以及反应温度等条件得到高选择性控制.

关键词： 芳酰甲亚基丙二酸酯; Corey叶立德; 共轭加成; 环丙烷化

本文引用格式

陈文龙 , 李慧敏 , 杨鹏飞 , 郑东程 , 杨高升 . 2-芳甲酰基甲亚基丙二酸酯与Corey叶立德的反应[J]. 有机化学, 2023 , 43(4) : 1472 -1482 . DOI: 10.6023/cjoc202209014

Abstract

The reactions of 2-aroylmethylenemalonates with Corey ylide were studied. Corey ylide, prepared in-situ from 1.0 equiv. of trimethylsulfoxonium iodide and 2.5 equiv. of sodium hydride in N,N-dimethylformamide (DMF), reacted with 2-aroylmethylenemalonates at －23 ℃ via a conjugate addition/elimination sequence to give 2-(1-aroylvinyl)malonates. Corey ylide, prepared in-situ from 2.2 equiv of trimethylsulfoxonium iodide and 5.0 equiv. of sodium hydride in DMF, reacted with 2-aroylmethylenemalonates at －23 to 0 ℃ by a conjugate addition/elimination/conjugate addition/cyclopropanation sequence to give 2-(1-aroylcyclopropyl)malonates. Corey ylide, prepared in-situ from 1.1 equiv. of trimethylsulfoxonium iodide and 5.0 equiv. of potassium carbonate in DMF, reacted with 2-aroylmethylenemalonates at 0 ℃ via a conjugate addition/cyclopropanation sequence to give 2-aroyl-1,1-cyclopropanedicarboxylates. These three processes can be controlled with high chemoselectivity by simply adjusting the base, the reagent ratios and the reaction temperature.

Key words： aroylmethylidene malonate; Corey ylide; conjugate addition; cyclopropanation

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