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

• DOI: 10.1021/acs.orglett.1c02306
• Publication Date: 2021-08-03T15:27:01Z
• Authors: Yuming Li; Jiyang Jie; Hongyun Li; Haijun Yang; Hua Fu
• Keywords: Oxindole; Synthon

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 C1 synthons at C-3 of oxindole unit 2-methylidenetrimethylene carbonate was 1,4-dipole. The cycloannulation performed room temperature provided corresponding good excellent yields. present method affords a new strategy for construction spirooxindole derivatives with unique three-dimensional structures.