Cationic Gold(I)-Catalyzed Intramolecular Cyclization of γ-Hydroxyalkynones into 3(2H)-Furanones

Masahiro Egi, Kenji Azechi, Moriaki Saneto, Kaori Shimizu and Shuji Akai*

*School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526, Japan, Email: akaiu-shizuoka-ken.ac.jp

M. Egi, K. Azechi, M. Saneto, K. Shimizu, S. Akai, J. Org. Chem., 2010, 75, 2123-2126.

DOI: 10.1021/jo100048j

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Abstract

A catalyst generated from the combination of (p-CF₃C₆H₄)₃PAuCl and AgOTf cyclizes readily available γ-hydroxyalkynones under mild conditions to give substituted 3(2H)-furanones in good yields. This method is also applicable to the preparation of 2,3-dihydro-4H-pyran-4-ones.

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proposed mechanism

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Key Words

3(2H)-furanones

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ID: J42-Y2010-0830