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An efficient synthetic chiral modifier for platinum

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

In: Catalysis Letters, 2005, vol. 102, no. 3-4, p. 121-125

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    Titre
    • An efficient synthetic chiral modifier for platinum
    Auteur
    • Diezi, Simon. Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH-Hönggerberg, CH-8093, Zürich, Switzerland
    • Hess, Marco. Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH-Hönggerberg, CH-8093, Zürich, Switzerland
    • Orglmeister, Elisabeth. Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH-Hönggerberg, CH-8093, Zürich, Switzerland
    • Mallat, Tamas. Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH-Hönggerberg, CH-8093, Zürich, Switzerland
    • Baiker, Alfons. Department of Chemistry and Applied Biosciences, Swiss Federal Institute of Technology, ETH-Hönggerberg, CH-8093, Zürich, Switzerland
    Type de document
    • Postprint
    Langue
    • Anglais
    Publié dans
    • Catalysis Letters, 2005, vol. 102, no. 3-4, p. 121-125. Kluwer Academic Publishers-Plenum Publishers
    Autre version électronique
    Identifiant OAI-PMH
    • oai:doc.rero.ch:318000
    Summary
    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 (10bar, 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)