Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Enantioface-Differentiating (Asymmetric) Hydrogenation of β-Ketoester with Modified Raney Nickel Catalyst (MRNi). XXXI. A Comparative Study of Reaction Rates and Optical Yields
Hiroshi OzakiAkira TaiShinzo KobatakeHironobu WatanabeYoshiharu Izumi
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1978 Volume 51 Issue 12 Pages 3559-3563

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Abstract

Enantioface-differentiating hydrogenations of methyl acetoacetate over (S)-alanine-, (S)-2-aminobutyric acid, (S)-valine-, (S)-leucine-, (S) -malic acid-, and (R,R)-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, vS and vR, were investigated. The rates of hydrogenation, v=vS+vR, were the same for all the amino acid-MRNi and also for all the hydroxy dicarboxylic acid-MRNi. However, the vRvs 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.

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