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Enantioselective hydrogenation of 2-methyl-2-pentenoic acid over cinchonidine-modified Pd/alumina

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Abstract

A chiral alkanoic acid was prepared with up to 52% excess of the (S) enantiomer by hydrogenating anα,β-unsaturated carboxylic acid with a cinchonidine-Pd/Al2O3 catalyst system. Favourable conditions are: high surface hydrogen concentration (⩾ 60 bar hydrogen pressure, low catalyst concentration and apolar solvents), near ambient temperature and a cinchonidine/reactantmolar ratio of at least 0.4 mol%. It is proposed that high hydrogen solubility and the presence of 2-methyl-2-pentenoic acid reactant as dimers are advantageous for enantiodifferentiation.

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Authors and Affiliations

  1. Department of Chemical Engineering and Industrial Chemistry, Swiss Federal Institute of Technology, ETH-Zentrum, CH-8092, Zurich, Switzerland

    K. Borszeky, T. Mallat & A. Baiker

Authors
  1. K. Borszeky
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  2. T. Mallat
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  3. A. Baiker
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Borszeky, K., Mallat, T. & Baiker, A. Enantioselective hydrogenation of 2-methyl-2-pentenoic acid over cinchonidine-modified Pd/alumina. Catal Lett 41, 199–202 (1996). https://doi.org/10.1007/BF00811491

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  • DOI: https://doi.org/10.1007/BF00811491

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