有机化学 ›› 2015, Vol. 35 ›› Issue (4): 898-904.DOI: 10.6023/cjoc201411026 上一篇    下一篇

研究简报

离子液体中氯钯化启动的串联环化构建饱和γ-丁内酯反应研究

李建晓a, 李春生a, 杨少容a, 罗维b   

  1. a 华南理工大学化学与化工学院 广州 510640;
    b 华南理工大学分析测试中心 广州 510640
  • 收稿日期:2014-11-14 修回日期:2014-12-03 出版日期:2015-04-25 发布日期:2014-12-15
  • 通讯作者: 杨少容 E-mail:lisryang@scut.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 21102047, 31101221)资助项目.

Chloropalladation Triggering the Cascade Annulation to Construct Functionalized Saturated γ-Lactones in Ionic Liquids

Li Jianxiaoa, Li Chunshenga, Yang Shaoronga, Luo Weib   

  1. a School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640;
    b Analytical and Testing Center, South China University of Technology, Guangzhou 510640
  • Received:2014-11-14 Revised:2014-12-03 Online:2015-04-25 Published:2014-12-15
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21102047, 31101221).

室温条件下, 发展了一种串联高效、高选择性地构建官能团化的饱和γ-丁内酯的新方法. 实验表明, 以易得的炔烃衍生物和4-戊烯酸为底物, PdCl2为催化剂, CuCl2·2H2O为氧化剂, 离子液体[C2O2mim]Cl为溶剂, 无添加配体的情况下, 以中等及优良的产率(69%~93%)合成了系列官能团化的饱和γ-丁内酯衍生物. 其结构均经1H NMR、13C NMR、MS 及HRMS 确证. 该方法具有反应条件温和、底物适用范围广、环境友好等优点, 为含饱和γ-丁内酯结构单元的天然产物及复杂药物分子的合成提供了一种新途径.

关键词: 离子液体, 氯钯化, 炔烃, 4-戊烯酸, 饱和γ-丁内酯

A highly efficient and mild palladium-catalyzed cascade annulation has been developed to afford functionalized γ-lactones in moderate to good yields with high regio- and diastereo-selectivities in ionic liquids. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. Moreover, this reaction provided a novel and convenient methodology for the construction of naturally occurring biologically active γ-lactones.

Key words: ionic liquids, chloropalladation, alkynes, pent-4-enoic acid, saturated γ-lactones