Yang Tongtong, Du Weiyao, Wu Congzheng, Qu Jiaxin, Sun Chentong, Zhao Xin, Guo Hongchao, Wang Chang, Wang Haiyang
School of Pharmaceutical Sciences and Institute of Materia Medica, Medical Science and Technology Innovation Center, Shandong First Medical University and Shandong Academy of Medical Sciences, Jinan, Shandong 250117, P. R. China.
Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. China.
Org Lett. 2025 Jan 24;27(3):715-721. doi: 10.1021/acs.orglett.4c03633. Epub 2025 Jan 9.
In this work, we developed a phosphine-catalyzed cascade lactonization/[2 + 1] annulation reaction between vinyl oxiranes and sulfonium compounds for the highly diastereoselective construction of spiro-2(3)-furanone skeletons. The cascade cycloaddition proceeds via the 2(5)-furanone phosphonium intermediate, introducing an oxygen-containing active intermediate for phosphine catalysis. These findings highlight the significant potential of harnessing vinyl oxiranes as versatile synthons for constructing spirocyclic compounds through simultaneous multicyclic skeleton formation.
在这项工作中，我们开发了一种膦催化的环氧化乙烯与锍化合物之间的串联内酯化/[2 + 1]环化反应，用于高非对映选择性构建螺-2(3)-呋喃酮骨架。该串联环加成反应通过2(5)-呋喃酮鏻中间体进行，引入了一种用于膦催化的含氧活性中间体。这些发现突出了利用环氧化乙烯作为通用合成子通过同时形成多环骨架来构建螺环化合物的巨大潜力。
