Cationic gold(I)-catalyzed intramolecular cyclization of gamma-hydroxyalkynones into 3(2H)-furanones.

J Org Chem

School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526, Japan.

Published: March 2010

The combination of (p-CF(3)C(6)H(4))(3)PAuCl and AgOTf generates a powerful catalyst for the intramolecular cyclizations of readily available gamma-hydroxyalkynones under mild conditions. The substituted 3(2H)-furanones are obtained in 55-94% yields. This method is also applicable to the preparation of 2,3-dihydro-4H-pyran-4-ones.

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http://dx.doi.org/10.1021/jo100048jDOI Listing

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