Solvent-Controlled Sc(OTf)_(3)-Catalyzed Ring Opening Reaction of 2-(Hetero)aryl-N-sulfonylazetidines:Synthesis of Allylic Amines/1,3-Oxazinane Derivatives  

溶剂控制三氟甲烷磺酸钪催化2-(杂)芳基-N-磺酰基吖丁啶开环反应:烯丙胺/1,3-噁嗪衍生物的合成

作　　者：Zhu Jie Tang Sidan Kan Xiumei Fan Shizhu Wang Pengfei Yang Peijun 朱洁;汤思丹;阚秀妹;凡士柱;王鹏飞;杨培俊(安徽工程大学化学与环境工程学院,功能配合物材料化学与应用安徽省重点实验室,安徽芜湖241000;安徽师范大学化学与材料科学学院,分子基材料省级实验室,安徽芜湖241002)

机构地区：[1]Anhui Province Key Laboratory of Functional Coordinated Complexes for Materials Chemistry and Application,School of Chemical and Environmental Engineering,Anhui Polytechnic University,Wuhu,Anhui 241000 [2]Anhui Laboratory of Molecular-Based Materials,College of Chemistry and Materials Science,Anhui Normal University,Wuhu,Anhui 241002

出　　处：《有机化学》2024年第9期2796-2809,共14页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.22001007);安徽工程大学科研基金(No.2020YQQ025);安徽省重点分子基材料省级实验室开放基金(No.fzj22012)资助项目.

摘　　要：Allylic amines and 1,3-oxazinanes are valuable molecular skeletons in organic synthesis and pharmaceutical industry.A straightforward way to such two types of compounds by solvent-controlled rare-earth metal Lewis acid-catalyzed transformations of 2-(hetero)aryl-N-sulfonylazetidines:the ring-opening isomerization of azetidines to allylic amines and the annulation of azetidines with aldehydes to 1,3-oxazinanes are reported.These two reactions feature scalability,low catalyst loading,mild reaction conditions,excellent yields and regioselectivity with demonstrated utility in three-step product transformations to naftifine,abamine and abamine SG.烯丙胺和1,3-噁嗪烷是有机合成和医药工业中有重要价值的分子骨架.报道了一种通过溶剂控制稀土金属路易斯酸催化2-(杂)芳基-N-磺酰基吖丁啶与醛环加成合成1,3-噁嗪烷以及自身开环异构化合成烯丙胺.这两种反应具有底物适用范围广、催化剂用量低、反应条件温和、产率高和区域选择性好等特点,并通过将产物三步转化为萘替酚、阿拉明和阿拉明SG证明了其实用价值.

关 键 词：rare-earth metal Lewis acid solvent control AZETIDINE regioselectivity ring opening reaction 

分 类 号：O621.251[理学—有机化学]