Direct resolution of α-monoalkyl-α-aryloxyacetic acids via ester or imide derivatives

Article abstract of DOI:10.1016/S0014-827X(97)00010-4

This paper describes a simple procedure for the resolution of racemic α-monoalkyl α-aryloxyacetic acids, using the chromatographic separation of their covalent derivatives. (R)-Ethyl mandelate, (R)-pantolactone and (S)-4-(1-methylethyl)-2-oxazolidinone are the resolving agents involved in the formation of equimolecular diastereomeric mixtures of esters or imides. Chromatographic resolutions were performed by means of gas chromatography (GC), thin-layer chromatography (TLC) and flash chromatography. Successive hydrolysis of separated diastereomers provided optically pure aryloxyacetic acids.