DIRECT RESOLUTION OF ALPHA-MONOALKYL-ALPHA-ARYLOXYACETIC ACIDS VIA ESTER OR IMIDE DERIVATIVES

This paper describes a simple procedure for the resolution of racemic alpha-monoalkyl alpha-aryloxyacetic acids, using the chromatographic s eparation of their covalent derivatives. (R)-Ethyl mandelate, (R)-pant olactone and (S)-4-(1-methylethyl)-2-oxazolidinone are the resolving a gents involved in the formation of equimolecular diastereomeric mixtur es of esters or imides. Chromatograpkic 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. (C) 1998 Elsevier Scienc e S.A.