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Mechanistic Insight into the Conversion of Tetrose Sugars to Novel α-Hydroxy Acid Platform Molecules

Authors

  • Michiel Dusselier,

    1. Centre for Surface Chemistry and Catalysis, Katholieke Universiteit Leuven, Kasteelpark Arenberg 23, 3001 Leuven (Belgium), Fax: (+32) 16-321-998
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  • Pieter Van Wouwe,

    1. Centre for Surface Chemistry and Catalysis, Katholieke Universiteit Leuven, Kasteelpark Arenberg 23, 3001 Leuven (Belgium), Fax: (+32) 16-321-998
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  • Filip de Clippel,

    1. Centre for Surface Chemistry and Catalysis, Katholieke Universiteit Leuven, Kasteelpark Arenberg 23, 3001 Leuven (Belgium), Fax: (+32) 16-321-998
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  • Jan Dijkmans,

    1. Centre for Surface Chemistry and Catalysis, Katholieke Universiteit Leuven, Kasteelpark Arenberg 23, 3001 Leuven (Belgium), Fax: (+32) 16-321-998
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  • Prof. Dr. David W. Gammon,

    1. Department of Chemistry—University of Cape Town, Private Bag, Rondebosch, 7701 (South Africa), Fax: (+27) 21-689-7499
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  • Prof. Dr. Bert F. Sels

    Corresponding author
    1. Centre for Surface Chemistry and Catalysis, Katholieke Universiteit Leuven, Kasteelpark Arenberg 23, 3001 Leuven (Belgium), Fax: (+32) 16-321-998
    • Centre for Surface Chemistry and Catalysis, Katholieke Universiteit Leuven, Kasteelpark Arenberg 23, 3001 Leuven (Belgium), Fax: (+32) 16-321-998
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Abstract

α-Hydroxy acids (AHAs) such as lactic acid are considered platform molecules in the biorefinery concept and have high-end applications in solvents and biodegradable polyester plastics. The synthesis of AHAs with a four-carbon backbone structure is a recently emerging field. New biomass-related routes towards their production could stimulate their practical use in new polyester plastics. Herein, we report the unique catalytic activity of soluble tin metal salts for converting tetroses, namely erythrulose and erythrose, into new four-carbon-backbone AHAs such as methyl vinylglycolate and methyl-4-methoxy-2-hydroxybutanoate. An in situ NMR study together with deuterium labeling experiments and control experiments with intermediates allowed us to propose a detailed reaction pathway.

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