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  • An Asymmetric Synthesis of ...
    Rubush, David M; Morges, Michelle A; Rose, Barbara J; Thamm, Douglas H; Rovis, Tomislav

    Journal of the American Chemical Society, 08/2012, Letnik: 134, Številka: 33
    Journal Article

    The desymmetrization of p-peroxyquinols using a Brønsted acid-catalyzed acetalization/oxa-Michael cascade was achieved in high yields and selectivities for a variety of aliphatic and aryl aldehydes. Mechanistic studies suggest that the reaction proceeds through a dynamic kinetic resolution of the peroxy hemiacetal intermediate. The resulting 1,2,4-trioxane products were derivatized and show potent cancer cell-growth inhibition.