Asymmetric synthesis of axially chiral, unsymmetrical diphenic acids via intramolecular Ullmann coupling reaction.
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概要
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A practical route to unsymmetrical diphenic acids is described. Successive esterification of ethylene glycol with two different 2-halobenzoyl chlorides gave the corresponding mixed diester, which was treated with copper powder in boiling DMF under dilution conditions. Silica-gel column chromatography allowed ready separation of the intramolecularly coupled cyclic diester (30–60% yield) from other by-products accompanying the Ullmann reaction, and alkaline hydrolysis gave unsymmetrical diphenic acid. Axially chiral, unsymmetrical diphenic acids of more than 99% enantiomeric excess were obtained from the reaction of mixed diesters prepared from (<I>R</I>)-1,1′-bi-2-naphthol.
- 公益社団法人 日本化学会の論文
著者
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Miyano Sotaro
Department Of Biochemistry And Engineering Faculty Of Engineering Tohoku University
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Handa Shigeru
Department Of Electronic Engineering Faculity Of Engineering Tohoku University
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Fukushima Hiroshi
Department Of Materials Science Faculty Of Engineering The University Of Tokyo:(present Address) Dep
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Hashimoto Harukichi
Department of Applied Chemistry, Faculty of Engineering, Tohoko University
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Ito Hiromitsu
Department of Applied Chemistry, Faculty of Engineering, Tohoku University
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Handa Shigeru
Department of Applied Chemistry, Faculty of Engineering, Tohoku University
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Miyano Sotaro
Department of Applied Chemistry, Faculty of Engineering, Tohoku University
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