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Greener Methodology: An Aldol Condensation of an Unprotected C-Glycoside with Solid Base Catalysts

Julie Zimmerman, Paul Anastas and 6 other contributors

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    Publication Date
    JUN
    Journal
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING
    Location
    https://doi.org/10.1021/acssuschemeng.8b00816
    Citation
    de Winter, T. ., Petitjean, L. ., Erythropel, H. ., Moreau, M. ., Hitce, J. ., Coish, P. ., … Anastas, P. . (2018). Greener Methodology: An Aldol Condensation of an Unprotected C-Glycoside with Solid Base Catalysts. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 6(6), 7810-7817. https://doi.org/10.1021/acssuschemeng.8b00816 (Original work published 2024)

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    Faculty
    Julie Zimmerman

    Julie Zimmerman Vice Provost for Planetary Solutions, Professor of Green Engineering, Deputy Director for Research at Center for Green Chemistry and Green Engineering

    Faculty
    Paul Anastas

    Paul Anastas Teresa and H. John Heinz III Professor in the Practice of Chemistry for the Environment

    Abstract

    The development of a new enamine-solid-base-catalyzed (ESBC) methodology for the aldol condensation reaction is reported. Solid base catalysts [nonactivated and activated magnesium oxide (MgO and MgOact) and calcium oxide (CaO and CaOact), a hydrotalcite (HT), and a porous metal oxide (PMO)] were investigated as safer and greener alternatives to previously reported catalytic systems. Multiple reaction parameters (temperature, solvent, time, and catalyst loading) were investigated todetermine optimal conditions for the practitioner to employ in the synthesis of C-glycosides. The optimized reaction conditions provided highly functionalized (E)alpha,beta-unsaturated ketones from unprotected C-glycosides in good to excellent yields. Moreover, the ESBC methodology is applicable to a wide range of aromatic aldehydes that feature electron-rich and electron-poor moieties, as well as sterically bulky groups. Lastly, the recyclability of the MgO catalyst was demonstrated.