Ag_(2)O/PPh_(3)催化2-氮杂丙烯酸酯构建4-位季碳氮杂吡咯烷的研究  

Study on the Construction of 4-position Quaternary Carbon Aza-pyrrolidines Using Ag_(2)O/PPh_(3)-catalyzed 2-azazcrylate

作　　者：罗岚峰 黄镇城 苏靖淳 陈羽 赵学辉 王海飞 Luo Lanfeng;Huang Zhencheng;Su Jingchun;Chen Yu;Zhao Xuehui;Wang Haifei(Hunan University of Technology College of Life Science and Chemistry,Zhuzhou 412007,China;Shenzhen Glareway Technology Co.,Ltd.,Shenzhen 518109,China)

机构地区：[1]湖南工业大学生命科学与化学学院,湖南株洲412007 [2]深圳市冠为科技股份有限公司,广东深圳518109

出　　处：《广东化工》2025年第6期25-26,24,共3页Guangdong Chemical Industry

基　　金：湖南省教育厅资助重点项目(21A0365);湖南省自然科学基金资助项目(2023JJ60446)。

摘　　要：4-位季碳氮杂吡咯烷作为一类重要的五元杂环化合物,其骨架单元在许多活性天然产物和药物分子中广泛存在,实现此类骨架的合成将具有重要的意义。本文以Ag_(2)O/PPh_(3)为催化体系,在有机碱三乙胺的作用下探索偶氮甲碱叶立德与2-氮杂丙烯酸酯之间的[3+2]环加成反应。通过反应条件优化和底物适应性研究,以54%~93%的产率高非对映选择性的实现了12个4-位季碳氮杂吡咯烷类衍生物的合成。该合成反应条件温和、原料廉价易得、底物适应性较广。As an important class of five membered heterocyclic compounds,4-position quaternary carbon nitroge-heterocyclic compounds are important skeleton motifs widely present in many active natural products and drug molecules.Therefore,the synthesis of such skeletons will be of great significance.This paper explores the[3+2]cycloaddition reaction between azomethine ylides and 2-azacrylate using Ag_(2)O/PPh_(3)as the catalytic system under the action of organic base triethylamine.By optimizing reaction conditions and studying substrate adaptability,twelve 4-position quaternary carbon aza-pyrrolidine derivatives were synthesized with high diastereoselectivity in 54%~93%yields.The synthesis reaction conditions are mild,the raw materials are cheap and easy to obtain,and the substrate adaptability is wide.,the cycloaddition reaction has the following features:mild reaction conditions,cheap and easily accessible raw materials and wide substrate adaptability.

关 键 词：2-氮杂丙烯酸酯 偶氮甲碱叶立德 氮杂吡咯烷 [3+2]环加成 

分 类 号：TQ[化学工程]