Dynamic kinetic resolution of alpha-bromoesters containing lactamides as chiral auxiliaries

2004 ARKIVOC  
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 4chlorophenoxide, 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.
doi:10.3998/ark.5550190.0005.532 fatcat:nzd3ldxscfdv3hl2cnobt7pddi