Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (5): 1535-1548.DOI: 10.6023/cjoc202311002 Previous Articles     Next Articles

ARTICLES

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*()   

  1. 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 发布日期: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

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()   

  1. College of Chemistry and Chemical Engineering, Shannxi Key Laboratory of Phytochemistry, Baoji University of Arts and Sciences, Baoji, Shaanxi 721013
  • Received:2023-11-02 Revised:2024-01-17 Published:2024-02-07
  • Contact: *E-mail: zhuhaitaobwl@163.com; zhouni13_2008@163.com; wangdongmay@163.com
  • 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

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