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An efficient synthetic chiral modifier for platinum

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Abstract

A new chiral modifier pantoyl-naphthylethylamine (PNEA) was synthesized by reductive alkylation of 1-(1-naphthyl)ethylamine with ketopantolactone. Platinum-on-alumina modified by PNEA afforded 93% ee and 100% chemoselectivity in the hydrogenation of the activated carbonyl group of 1,1,1-trifluoro-2,4-pentanedione. Reductive heat treatment and ultrasonication of the catalyst, and the use of chlorinated solvents under mild conditions (10 bar, 10 °C) enhanced the enantioselectivity. This is the first case in heterogeneous catalysis that a synthetic modifier gives more than 90% ee, better than the commonly used modifier of natural origin (cinchonidine or O-methyl-cinchonidine).

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Authors and Affiliations

  1. Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH-Hönggerberg, CH-8093, Zürich, Switzerland

    Simon Diezi, Marco Hess, Elisabeth Orglmeister, Tamas Mallat & Alfons Baiker

Authors
  1. Simon Diezi
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  2. Marco Hess
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  3. Elisabeth Orglmeister
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  4. Tamas Mallat
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  5. Alfons Baiker
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Correspondence to Alfons Baiker.

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Diezi, S., Hess, M., Orglmeister, E. et al. An efficient synthetic chiral modifier for platinum. Catal Lett 102, 121–125 (2005). https://doi.org/10.1007/s10562-005-5842-x

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  • DOI: https://doi.org/10.1007/s10562-005-5842-x

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