The conversion of racemic α-bromobutanoic acid into the corresponding esters with amides of (S)-lactic acid as chiral auxiliaries was examinated. Displacement of the bromine with 4-chlorophenoxide, under suitable reaction conditions, was found to proceed with good to high diastereoselectivity to give 4-(chlorophenoxy)butanoyl esters. After hydrolysis, the (R)-enantiomer of antilipidemic 2-(4-chlorophenoxy)butanoic acid was obtained.
Dynamic kinetic resolution of α-bromoesters containing lactamides as chiral auxiliaries
AMMAZZALORSO, Alessandra;AMOROSO, Rosa;DE FILIPPIS, Barbara;GIAMPIETRO, Letizia;MACCALLINI, Cristina;
2004-01-01
Abstract
The conversion of racemic α-bromobutanoic acid into the corresponding esters with amides of (S)-lactic acid as chiral auxiliaries was examinated. Displacement of the bromine with 4-chlorophenoxide, under suitable reaction conditions, was found to proceed with good to high diastereoselectivity to give 4-(chlorophenoxy)butanoyl esters. After hydrolysis, the (R)-enantiomer of antilipidemic 2-(4-chlorophenoxy)butanoic acid was obtained.File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
