Synthesis of α-Hydroxy-β-triflamido Carboxylic Esters through Ring-Opening of Alkoxycarbonyl Oxiranes

ABSTRACT The oxirane ring of 3-alkyl- and 3-arylglycidic esters has been opened with trifluoromethanesulfonamide (TfNH 2 ) under solid-liquid heterogeneous conditions. The corresponding α-hydroxy-β-triflamido esters were produced in good yields, in a regio- and stereoselective fashion. Several reaction parameters, such as the nature of the base, the presence of a phase transfer catalyst and/or a solvent have been examined.