Guanidinium hypoiodite-catalyzed intramolecular oxidative coupling reaction of oxindoles with β-dicarbonyls

• Main Authors: Sugimoto, Kota, Mori, Io, Kato, Takanari, Yasui, Koji, Xu, Ban, Tan, Choon-Hong, Odagi, Minami, Nagasawa, Kazuo
• Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
• Format: Article
• Language: English
• Published: 2023
• Subjects: Science::Chemistry; Catalysts; Guanidine
• Online Access: https://hdl.handle.net/10356/168938
• Institution: Nanyang Technological University

Spiro[indoline-3,4'-piperidine] is a fundamental motif present in various biologically active compounds. Here, we report an intramolecular oxidative coupling reaction of oxindoles with β-dicarbonyls in the presence of a guanidinium hypoiodite catalyst, providing spiro-coupling products in moderate to excellent yields. Furthermore, a chiral hypoiodite catalyst derived from the chiral guanidinium organocatalyst is effective for the challenging asymmetric carbon-carbon bond-forming reaction, affording optically active spiro[indoline-3,4'-piperidines].