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2024 , Vol. 44 >Issue 5: 1535 - 1548

DOI: https://doi.org/10.6023/cjoc202311002

研究论文

银催化环状Morita-Baylis-Hillman醇及其类似物与芳基乙烯的顺式[5＋2]环加成反应研究

  • 崔永伟 ,
  • 梁春苗 ,
  • 祝海涛 ,
  • 申成平 ,
  • 任飞扬 ,
  • 孙梦涵 ,
  • 赵媛 ,
  • 王文静 ,
  • 王冬梅 ,
  • 周妮妮
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  • 宝鸡文理学院化学化工学院 陕西省植物化学重点实验室 陕西宝鸡 721013

收稿日期: 2023-11-02

  修回日期: 2024-01-17

  网络出版日期: 2024-02-07

基金资助

陕西省自然科学基金(2021JQ-802); 陕西省教育厅科研计划(21JK0476); 陕西省创新能力推进计划(2022TD-63); 秦岭药用植物及有机功能分子研究与开发利用创新团队资助项目

收起

cis-Selective [5＋2]-Cycloaddition Reactions of Cyclic Morita-Baylis- Hillman Alcohols and Its Analogues with Arylethylenes Catalyzed by Ag(I)

  • Yongwei Cui ,
  • Chunmiao Liang ,
  • Haitao Zhu ,
  • Chengping Shen ,
  • Feiyang Ren ,
  • Menghan Sun ,
  • Yuan Zhao ,
  • Wenjing Wang ,
  • Dongmei Wang ,
  • Nini Zhou
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  • College of Chemistry and Chemical Engineering, Shannxi Key Laboratory of Phytochemistry, Baoji University of Arts and Sciences, Baoji, Shaanxi 721013
*E-mail: ;
;

Received date: 2023-11-02

  Revised date: 2024-01-17

  Online published: 2024-02-07

Supported by

Natural Science Foundation of Shaanxi Province(2021JQ-802); Scientific Research Program Funded by Shaanxi Provincial Education Department(21JK0476); Innovation Capability Support Program of Shaanxi Province(2022TD-63); Innovation R&D Team of BUAS on Qinling Medicinal Plants and Functional Organic Molecules

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摘要

开发了AgSbF6催化环状Morita-Baylis-Hillman醇及其类似物与芳基乙烯的顺式[5＋2]环加成反应, 同时有效构建了茚酮稠合苯并[7]轮烯骨架化合物. 密度泛函理论(DFT)计算结果表明, 1,3-顺式选择性可能受动力学控制. 二氢二苯并[a,f]薁-12-酮产物3a可以通过区域选择性的氢化和环丙烷化反应进行衍生化.

关键词： Morita-Baylis-Hillman醇; 芳基乙烯; 银催化; [5＋2]环加成

本文引用格式

崔永伟 , 梁春苗 , 祝海涛 , 申成平 , 任飞扬 , 孙梦涵 , 赵媛 , 王文静 , 王冬梅 , 周妮妮 . 银催化环状Morita-Baylis-Hillman醇及其类似物与芳基乙烯的顺式[5＋2]环加成反应研究[J]. 有机化学, 2024 , 44(5) : 1535 -1548 . DOI: 10.6023/cjoc202311002

Abstract

An AgSbF6-catalyzed diastereoselective [5＋2]-cycloaddition reaction was developed as an efficient entry into indanone-fused benzo[7]annulene frameworks from cyclic Morita-Baylis-Hillman alcohols and its analogues with aryl- ethylenes. Density functional theory (DFT) calculation data analysis shows that 1,3-cis-selectivity might be mainly controlled by kinetics. The resulting dihydrodibenzo[a,f]azulen-12-one 3a can be further functionalized by using the regioselective hydrogenation and cyclopropanation.

Key words： Morita-Baylis-Hillman alcohol; arylethylenes; silver catalysis; [5＋2]-cycloaddition

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