A facile solid-phase synthesis of substituted 2(5H)-furanones from polymer-supported alpha-selenocarboxylic acids. - Suppr | 超能文献

A facile solid-phase synthesis of substituted 2(5H)-furanones from polymer-supported alpha-selenocarboxylic acids.

作者信息

Huang Xian, Sheng Shou-Ri

机构信息

Department of Chemistry, Zhejiang University, Xixi Campus, Hangzhou, 310028, P. R. China.

出版信息

J Comb Chem. 2003 May-Jun;5(3):273-7. doi: 10.1021/cc020066l.

DOI:10.1021/cc020066l

Abstract

The synthesis of polystyrene-supported alpha-selenoacetic acid, alpha-selenopropionic acid, and alpha-selenophenylacetic acid is described. The reaction of the dilithio derivatives of polymer-supported alpha-selenocarboxylic acids with racemic epoxides or optically active styrene oxide afforded polystyrene-supported gamma-substituted alpha-selenobutyrolactones. The alpha-alkylation reaction of gamma-substituted polystyrene-supported alpha-selenobutyrolactones provided another route for the synthesis of polystyrene-supported alpha,gamma-disubstituted alpha-selenobutyrolactones. Subsequent oxidation-elimination with an excess of 30% hydrogen peroxide at room temperature afforded substituted (3- and 5-mono-; 3,4- and 3,5-di) 2(5H)-furanones in high yields and good purities.

摘要

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