Synthesis of Spiro-Epoxy oxindole derivatives via unexpected oxidation/consecutive Corey-Chaykovsky reaction. (21st December 2022)

• Record Type: Journal Article
• Authors: Chae, Min Ki; Ko, Haye Min
• Is Part Of: Tetrahedron letters. Volume 113(2022)
• Publication Date: 2022-12-21
• Subjects: Corey-Chaykovsky reaction -- Spiro-epoxy oxindole -- One-Pot process -- Oxidation -- N-2, 2, 2-Trifluoroethylisatin ketimine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.154251
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Unexpected oxidation. Corey-Chaykovsky reaction. Facile one-pot process to synthesize spiro[indoline-3, 2′-oxiran]-2-ones. Abstract: Unexpected oxidation/consecutive Corey-Chaykovsky reaction of N -2, 2, 2-trifluoroethylisatin ketimines is conducted via a one-pot process using sulfur ylide to form spiro-epoxy oxindole derivatives. This unprecedented reaction proceeds smoothly under mild conditions, is operationally simple, and tolerates various functional groups. Notably, while the general Corey-Chaykovsky reaction of imines affords aziridines, this work describes the first oxidation step to produce isatins as intermediates followed by the Corey-Chaykovsky reaction.