Enantioface-differentiating (asymmetric) hydrogenation of .BETA.-ketoester with modified raney nickel catalyst (MRNi). XXXI. A comparative study of reaction rates and optical yields.
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概要
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Enantioface-differentiating hydrogenations of methyl acetoacetate over (<I>S</I>)-alanine-, (<I>S</I>)-2-aminobutyric acid, (<I>S</I>)-valine-, (<I>S</I>)-leucine-, (<I>S</I>) -malic acid-, and (<I>R</I>,<I>R</I>)-tartaric acid-MRNi were carried out under atmospheric pressure of hydrogen and the effects of the modifying reagent on the rates of the formation of enantiomer, <I>v</I><SUB>S</SUB> and <I>v</I><SUB>R</SUB>, were investigated. The rates of hydrogenation, <I>v</I>=<I>v</I><SUB>S</SUB>+<I>v</I><SUB>R</SUB>, were the same for all the amino acid-MRNi and also for all the hydroxy dicarboxylic acid-MRNi. However, the <I>v</I><SUB>R</SUB>⁄<I>v</I><SUB>s</SUB> ratios were different. These results are explained in terms of the independence of the rate-determining and enantioface-differentiating steps in the reaction pathway of hydrogenation. The rate-determining step of hydrogenation was shown to be the hydrogen addition to the adsorbed substrate, while the enantioface-differentiating step was expected to occur prior to the rate-determining step.
- 公益社団法人 日本化学会の論文
著者
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Ozaki Hiroshi
Division Of Nephrology Endocrinology And Vascular Medicine Tohoku University Graduate School Of Medi
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Izumi Yoshiharu
Division of Organic Chemistry Institute for Protein Research Osaka University
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Watanabe Hironobu
Division of Organic Chemistry, Institute for Protein Research, Osaka University
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Tai Akira
Division of Organic Chemistry, Institute for Protein Research, Osaka University
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Kobatake Shinzo
Division of Organic Chemistry, Institute for Protein Research, Osaka University
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