Highly enantioselective reduction of ethyl 2-acyloxy-3-oxobutanoate with immobilized Baker's yeast.
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概要
- 論文の詳細を見る
Reduction of ethyl 2-acetoxy-3-oxobutanoate (<B>4a</B>) with immobilized baker's yeast in calcium alginate gel gave a 18 : 19 : 63 mixture of ethyl (2<I>R</I>,3<I>S</I>)- and (2<I>S</I>,3<I>S</I>)-2-acetoxy-3-hydroxybutanoates and ethyl (2<I>S</I>,3<I>S</I>)-2,3-dihydroxybutanoate each with >95% e.e. in 58% yield. A similar treatment of a 2-benzoyloxy analog of <B>4a</B> afforded a 6 : 94 mixture of ethyl (2<I>R</I>,3<I>S</I>)- and (2<I>S</I>,3<I>S</I>)-2-benzoyloxy-3-hydroxybutanoates (>95% e.e.) in 70% yield. Their absolute configurations were determined by comparison with authentic (2<I>R</I>,3<I>S</I>)- and (2<I>S</I>,3<I>S</I>)-2,3-dihydroxybutanoic acids. Effects of the immobilization and the pH of culture solution on the product ratio are also discussed.
- 公益社団法人 日本化学会の論文
著者
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Sakai Takashi
Department Of Applied Chemistry Faculty Of Engineering Okayama University
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Utaka Masanori
Department Of Applied Chemistry Faculty Of Engineering Okayama University
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Nakamura Toshiki
Department of Neurology, Rehabilitation Amakusa Hospital
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Nakamura Toshiki
Department of Synthetic Chemistry, School of Engineering, Okayama University
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Amano Eiichiro
Department of Synthetic Chemistry, School of Engineering, Okayama University
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Takeda Akira
Department of Applied Chemistry, Faculty of Engineering, Okayama University
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Fukuda Katsuyoshi
Department of Synthetic Chemistry, School of Engineering, Okayama University
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