119061-16-4Relevant articles and documents
Direct resolution of α-monoalkyl-α-aryloxyacetic acids via ester or imide derivatives
Amoroso, Rosa,Bettoni, Giancarlo,Tricca, Maria Luisa,Loiodice, Fulvio,Ferorelli, Savina
, p. 73 - 79 (2007/10/03)
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.
Candida cylindracea lipase-mediated kinetic resolution of α-substituted α-aryloxyacetic acid methyl esters
Noya,Ferorelli,Franchini,Scilimati,Sinicropi,Tortorella
, p. 293 - 296 (2007/10/03)
Hydrolysis of several α-alkyl-α-aryloxyacetic acid methyl esters and of α-methyl-α-(n-propyl)-α-(p-chlorophenoxy)acetic acid methyl ester were performed in the presence of Candida cylindracea lipase. The α-alkyl-α-aryloxyacetic acid methyl esters and α-methyl-α-(n-propyl)-α-(p-chlorophenoxy)acetic acid methyl ester were incubated in buffer phosphate (pH 7-8). The reaction mixture, containing the unreacted ester and corresponding acid, showed enantiomeric excesses (ee) up to 81%. The extent of conversion was quite low for the α-methyl-α-(n-propyl)-α-(p-chlorophenoxy)acetic acid methyl ester, the corresponding acid was obtained with ee > 98%.