Synthesis of Spirotetrahydrofuran Oxindoles via Palladium-Catalyzed [4 + 1] Cycloaddition of Diphenyl 2-Oxoindolin-3-yl Phosphates and 2-Methylidenetrimethylene Carbonate

作者：Yuming Li, Jiyang Jie, Hongyun Li, Haijun Yang, Hua Fu · 发表于：Organic Letters · 年份：2021 · DOI：10.1021/acs.orglett.1c02306 · 被引用次数：28 · 研究领域：Oxidative Organic Chemistry Reactions、Cyclopropane Reaction Mechanisms、Asymmetric Synthesis and Catalysis

A novel palladium-catalyzed [4 + 1] cycloaddition to give spirotetrahydrofuran oxindoles has been developed, in which diphenyl 2-oxoindolin-3-yl phosphates were used as the both electrophilic and nucleophilic C 1 synthons at C-3 of the oxindole unit and 2-methylidenetrimethylene carbonate was used as the 1,4-dipole. The cycloannulation was performed at room temperature and provided the corresponding spirotetrahydrofuran oxindoles in good to excellent yields. The present method affords a new strategy for the construction of spirooxindole derivatives with unique three-dimensional structures.