Catalysis Letters

, Volume 31, Issue 2–3, pp 143–151 | Cite as

Chiral nitrogen compounds as new modifiers for the enantioselective hydrogenation of ethyl pyruvate

  • B. Minder
  • M. Schürch
  • T. Mallat
  • A. Baiker


The enantioselective hydrogenation of ethyl pyruvate to (R)- or (S)-ethyl lactate has been studied over alumina- and carbon-supported Pt-metal catalysts modified by various heterocyclic N-compounds and substituted amides. The reactions were carried out under mild conditions in acetic acid; other solvents had a detrimental effect on enantioselectivity. An enantiomeric excess (ee) of 67% and a rate acceleration by a factor of 6, compared to the unmodified catalyst, was observed with alumina-supported Pt modified by (R)-1-(1-naphthyl)ethylamine. In contrast, carbon-supported Pd, Ru and Rh were non-selective and only little active. The studies indicated that besides naphthyl or quinolyl groups, two separate phenyl groups or one phenyl group together with two amino groups can provide a suitable anchoring of the chiral modifier on the Pt surface. The nature of interaction between the modifiers and ethyl pyruvate is briefly discussed.


enantioselective hydrogenation chiral modifier ethyl pyruvate Pt/alumina 


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Copyright information

© J.C. Baltzer AG, Science Publishers 1995

Authors and Affiliations

  • B. Minder
    • 1
  • M. Schürch
    • 1
  • T. Mallat
    • 1
  • A. Baiker
    • 1
  1. 1.Department of Chemical Engineering and Industrial ChemistrySwiss Federal Institute of TechnologyZurichSwitzerland

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