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Short Paper | Special issue | Vol 88, No. 1, 2014, pp.817-825
Published online, 1st August, 2013
DOI: 10.3987/COM-13-S(S)66
■ Selective Synthesis of Benzyl Enol Ethers of β-Dicarbonyl Compounds in Basic Condition and the Application towards Synthesis of Naphthoquinones

Kazuaki Katakawa, Dai Yonenaga, Tomoyo Terada, Naoya Aida, Airi Sakamoto, Keishi Hoshino, and Takuya Kumamoto*

*Research Institute of Pharmaceutical Sciences, Musashino University, 1-1-20 Shinmachi Nishitokyo Tokyo, Japan

Abstract

Selective synthesis of benzyl enol ether of β-tetronic acids and β-dicarbonyl compounds in basic condition was examined. Benzylation of α-methyl-β-tetronic acid with benzyl tosylate in the presence of potassium carbonate gave the corresponding benzyl enol ether exclusively. The reaction of β-tetronic acid and cyclic 1,3-diketones gave the O-benzyl adducts preferentially than the C,O-dibenzylated ones. Diels-Alder reaction of furan derived the benzyl enol ether of α-methyl-β-tetronic acid and benzyne furnished the functionalized napthoquinone derivatives.