Convenient Formation of 4-Hydroxyalk-2-en-1-one Functionality via A Knoevenagel-type Carbon Chain Elongation Reaction of Aldehyde with 1-Arylsulfinylalkan-2-one

Junzo Nokami*, Kazuhide Kataoka, Kazuhiro Shiraishi, Masahiro Osafune, Iqbal Hussain, and Shin-ichi Sumida

*Department of Applied Chemistry, Faculty of Engineering, Okayama University of Science, 1-1 Ridai-cho, Okayama 700-0005, Japan

J. Nokami, K. Kataoka, K. Shiraishi, M. Osafune, I. Hussain, S.-i. Sumida, J. Org. Chem., 2001, 66, 1228-1232.

DOI: 10.1021/jo001323g

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Abstract

4-Hydroxyalk-2-en-1-ones as highly functionalized four-carbon units can conveniently be prepared by Knoevenagel reactions of aldehydes with 1-(arylsulfinyl)alkan-2-ones in the presence of diethylamine. The reaction tolerates carbonyl and hydroxy groups in both of the alkyl chains.

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proposed reaction pathway

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Key Words

Knoevenagel condensation, hydroxylation

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ID: J42-Y2001