Oxidation of Methyl Trimethylsilyl Ketene Acetals to α-Hydroxyesters with Urea Hydrogen Peroxide Catalyzed by Methyltrioxorhenium

Saša Stanković and James H. Espenson*

*Ames Laboratory and Department of Chemistry, Iowa State University, Ames, Iowa 50011

S. Stanković, J. H. Espenson, J. Org. Chem., 2000, 65, 5528-5530.

DOI: 10.1021/jo000212e

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Abstract

Methyltrioxorhenium (MTO) catalyzes an oxidation of methyl trimethylsilyl ketene acetals with urea hydrogen peroxide to afford α-hydroxy and α-siloxy esters. On treatment with potassium fluoride, the α-hydroxy esters are obtained in high yields.

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Key Words

Rubottom Oxidation, Methyltrioxorhenium, UHP, α-Hydroxy Esters

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ID: J42-Y2000