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
cis-Selective[5+2]-Cycloaddition Reactions of Cyclic Morita-Baylis-Hillman Alcohols and Its Analogues with Arylethylenes Catalyzed byAg(l)
崔永伟 1梁春苗 1祝海涛 1申成平 1任飞扬 1孙梦涵 1赵媛 1王文静 1王冬梅 1周妮妮1
作者信息
- 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
- 折叠
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.
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.
关键词
Morita-Baylis-Hillman醇/芳基乙烯/银催化/[5+2]环加成Key words
Morita-Baylis-Hillman alcohol/arylethylenes/silver catalysis/[5+2]-cycloaddition引用本文复制引用
基金项目
Innovation R&D Team of BUAS on Qinling Medicinal Plants and Functional Organic Molecules.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()
出版年
2024
NETL
NSTL
万方数据