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Metal-Free α-Hydroxylation of α-Unsubstituted β-Oxoesters and β-Oxoamides

Haruyasu Asahara and Nagatoshi Nishiwaki*

*School of Environmental Science and Engineering, and Research Center for Material Science and Engineering, Kochi University of Technology, Kami, Kochi 782-8502, Japan, Email: nishiwaki.nagatoshikochi-tech.ac.jp

H. Asahara, N. Nishiwaki, J. Org. Chem., 2014, 79, 11735-11739.

DOI: 10.1021/jo501985u (free Supporting Information)


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Abstract

A direct metal-free α-hydroxylation of α-unsubstituted β-oxoesters and β-oxoamides using m-chloroperbenzoic acid as the oxidant enables straightforward metal-free access to important α-hydroxy-β-dicarbonyl moieties under mild reaction conditions. Furthermore, the hydroxylated products can readily be converted into vicinal tricarbonyl compounds, which are useful synthetic precursors.

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Key Words

α-hydroxylation, MCPBA, 1,2-diketones, 1,2-ketoesters, Cu(OAc)2


ID: J42-Y2014