Biomimetic Direct Aldol Reaction of Pyruvate Esters with Chiral Aldehydes

Authors

  • Osama El-Sepelgy,

    Corresponding author
    1. Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Krakow, Poland
    • Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Krakow, Poland
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  • Jacek Mlynarski

    Corresponding author
    1. Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Krakow, Poland
    2. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, Warsaw, Poland
    • Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Krakow, Poland
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Abstract

Direct aldol reactions of pyruvate esters with sugar aldehydes is efficiently promoted by dinuclear metal complexes or chiral Cinchona alkaloid organocatalysts. Application of sterically hindered aryl esters enables the to-date problematic aldol reaction of pyruvate donors with syn- or anti-selectivity en route to the short and efficient synthesis of 3-deoxy-2-ulosonic acids.

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