Butane-2,3-Diacetal-Desymmetrized Glycolic Acid-A New Building Block for the Stereoselective Synthesis of Enantiopure #alpha#-Hydroxy Acids

摘要

Of the many classes of functional groups and motifs present in biologically and pharmacologically important compounds, mono-or dialkylated #alpha#-hydroxy acids occur commonly. As a result of this feature, a range of synthesis methods has appeared over the years. A commonly adopted strategy is the #alpha#-alkylation of chiral glycolic acid equivalents. Following our earlier reports using dispiroketal desymmetrization for this purpose, we here report the design, preparation, and alkylation reactions of a new chiral glycolic acid equivalent-the butande-2,3-diacetal-desymmetrized glycolate 1.