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Unexpected inversion of enantioselectivity during the hydrogenation of ethyl pyruvate using hydroquinine and hydroquinidine modified Pt/Al2O3

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Abstract

In the enantioselective hydrogenation of ethyl pyruvate using hydroquinidine 4-chlorobenzoate modified Pt/γ-Al2O3 catalyst, the sense of the enantioselectivity is a function of the modifier concentration. At low concentration (S)-ethyl lactate is preferred and at higher concentration (R)-ethyl lactate is formed; the opposite trend is observed with hydroquinine 4-chlorobenzoate. This is the first example where enantio-inversion is induced solely as a function of the chiral modifier concentration.

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Authors and Affiliations

  1. Department of Chemistry, Cardiff University, Cardiff, CF10 3AT, UK

    Robert L. Jenkins, Nicholas Dummer, Xiabao Li, Salem M. Bawaked, Paul McMorn, Richard P. K. Wells & Graham J. Hutchings

  2. Center for Advanced Materials and Nanotechnology, Lehigh University, Bethlehem, PA, 18015-3195, USA

    Andrew Burrows & Christopher J. Kiely

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  1. Robert L. Jenkins
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  2. Nicholas Dummer
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  3. Xiabao Li
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  4. Salem M. Bawaked
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  5. Paul McMorn
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  6. Richard P. K. Wells
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  7. Andrew Burrows
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  8. Christopher J. Kiely
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  9. Graham J. Hutchings
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Correspondence to Graham J. Hutchings.

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Jenkins, R.L., Dummer, N., Li, X. et al. Unexpected inversion of enantioselectivity during the hydrogenation of ethyl pyruvate using hydroquinine and hydroquinidine modified Pt/Al2O3 . Catal Lett 110, 135–138 (2006). https://doi.org/10.1007/s10562-006-0096-9

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  • DOI: https://doi.org/10.1007/s10562-006-0096-9

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