Synthesis of 5-Aryl-3(2H)-furanones Using Intramolecular Cyclization of Sulfonium Salts

Sho Inagaki*, Kai Saito, Soichiro Suto, Hiromi Aihara, Aoi Sugawara, Satoru Tamura, Tomikazu Kawano*

*Department of Medicinal and Organic Chemistry, School of Pharmacy, Iwate Medical University, Yahaba, Iwate 028-3694, Japan, Email: shoinagaiwate-med.ac.jp, tkawanoiwate-med.ac.jp

S. Inagaki, K. Saito, S. Suto, S. Suto, H. Aihara, A. Sugawara, S. Tamura, T. Kawano, J. Org. Chem., 2018, 83, 13834-13846.

DOI: 10.1021/acs.joc.8b02153

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Abstract

A base-induced intramolecular cyclization of (4-aryl-2,4-dioxobutyl)methylphenylsulfonium salts provides 2-unsubstituted 5-aryl-3(2H)-furanones in excellent yield within 10 min. This procedure is simple, and can be carried out under mild conditions and an ambient atmosphere.

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proposed mechanism

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Key Words

3(2H)-furanones

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ID: J42-Y2018