Synthesis and Lipase-Catalyzed Resolution of 5-(Hydroxymethyl)-1,3-dioxolan-4-ones: Masked Glycerol Analogs as Potential Building Blocks for Pharmaceuticals

(Hydroxymethyl)-1,3-dioxolan-4-ones from mandelic and lactic acids and 1,5,5-trimethyl-3-phenyloxazolidin-2-one from mandelamide were α-alkylated using benzyl chloromethyl ether. Reductive debenzylation of the products of alkylation unmasked the hydroxymethyl groups. The compounds obtained in this fashion were subsequently subjected to lipase-catalyzed resolution in organic media. Depending on the lipase and substrate employed, enantiomeric ratios up to E = 200 were observed. The obtained optically pure compounds can be considered as masked 2-substituted glycerol equivalents, which could be used for the preparation of tertiary (aryloxy)propanolamines, compounds having potential β-blocking activity.