金自接力催化1,3-烯炔醋酸酯与环醚缩醛的环化/亲核取代反应研究

doi:10.6023/cjoc202408027

有机化学

研究论文

金自接力催化1,3-烯炔醋酸酯与环醚缩醛的环化/亲核取代反应研究

张丛玉^†,a, 陈晓琦^†,a, 孟凡涛^a, 王海营^*,a, 郝文娟^a, 姜波^*,a

^a江苏师范大学化学与材料科学学院江苏徐州 221116

收稿日期:2024-08-22 修回日期:2024-10-16
作者简介:^†共同第一作者.
基金资助:
国家自然科学基金(No. 22271123)和国家级大学生创新创业训练计划(No. 202410320015Z)资助项目.

Gold Self-Relay Catalytic Annulation/Nucleophilic Substitution Cascade of 1,3-Enyne Acetates with Cyclic Ether Acetals

Zhang Cong-Yu^†,a, Chen Xiao-Qi^†,a, Meng Fan-Tao^a, Wang Hai-Ying^*,a, Hao Wen-Juan^a, Jiang Bo^*,a

^aSchool of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, 221116

Received:2024-08-22 Revised:2024-10-16
Contact: *E-mail: wanghy@jsnu.edu.cn (H.Y. Wang), jiangchem@jsnu.edu.cn (B. Jiang).
About author:^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China (No. 22271123) and National College Students’ Innovation and Entrepreneurship Training Program (No. 202410320015Z).

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摘要/Abstract

本文报道了一种新型金自接力催化1,3-烯炔醋酸酯与环醚缩醛参与的增环/亲核取代反应,高非对映选择性地合成具有环季碳中心的环醚化环戊烯酮衍生物,收率中等至良好,dr值>19:1。该催化反应通过调整1,3-烯炔醋酸酯的烯烃类型实现了两类碳环骨架构建。当使用具有环烯烃的1,3-烯炔醋酸酯时,高非对映选择性地合成了5-6稠合双碳环产物,而使用非环状1,3-烯炔醋酸酯时,则形成五元碳环骨架。值得一提的是,环醚缩醛在传统多步有机合成中常用做保护基团,而在此反应中,该试剂用作亲电性的环醚前体,实现旧试剂新用途。目前方法展现出良好官能团相容性、广泛底物范围和高非对映选择性等优点, 为官能化环戊烯酮衍生物的合成提供一类新合成策略.

关键词: 金自接力催化, Nazarov环化, 亲核取代反应, 1,3-烯炔醋酸酯, 环醚缩醛

A new gold self-relay catalytic annulation/nucleophilic substitution cascade of 1,3-enyne acetates with cyclic ether acetals is reported, enabling highly diastereoselective access to cyclic etherified cyclopentenones with cyclic quaternary centers in moderate to good yields and >19:1 dr. This catalysis enables the direct construction of two types of carboncyclic skeletons by adjusting the olefin types of 1,3-enyne acetates. When 1,3-enyne acetates bearing a cyclic alkene unit were used, 5-6 fused bicarbocyclic products were diastereoselectively synthesized, whereas the reaction of acyclic 1,3-enyne acetates resulted in five-memebered carbocyclic framework. Notably, cyclic ether acetals are commonly used as protecting groups in traditional multistep organic syntheses, and in this reaction, such reagents serve as electrophilic cyclic ether precursors, achieving new uses for old reagents. The current method demonstrates good functional group compatibility, a broad substrate scope and high diastereoselectivity, providing a new synthetic strategy toward functionalized cyclopentenones.

Key words: Gold self-relay catalysis, Nazarov cyclization, Nucleophilic substitution, 1,3-Enyne acetates, Cyclic ether acetals

引用此文

张丛玉, 陈晓琦, 孟凡涛, 王海营, 郝文娟, 姜波. 金自接力催化1,3-烯炔醋酸酯与环醚缩醛的环化/亲核取代反应研究[J]. 有机化学, doi: 10.6023/cjoc202408027.

Zhang Cong-Yu, Chen Xiao-Qi, Meng Fan-Tao, Wang Hai-Ying, Hao Wen-Juan, Jiang Bo. Gold Self-Relay Catalytic Annulation/Nucleophilic Substitution Cascade of 1,3-Enyne Acetates with Cyclic Ether Acetals[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202408027.

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金自接力催化1,3-烯炔醋酸酯与环醚缩醛的环化/亲核取代反应研究

Gold Self-Relay Catalytic Annulation/Nucleophilic Substitution Cascade of 1,3-Enyne Acetates with Cyclic Ether Acetals

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