ENZYMATIC AMINOLYSIS AND TRANSAMIDATION REACTIONS

Chiral amides can be obtained from (+/-)-2-chloropropionate esters and a wide range of amines when the reaction is catalyzed by Candida cylindracea lipase. The enantioselection of the enzyme in this aminolysis reaction depends on the substrate and nucleophile structure and reaction conditions. This lipase can catalyze a transamidation reaction if N-trifluoroethyl-2-chloropropionamide is used as substrate. In this way, amides are obtained in high-moderate enantiomeric excesses. The aminolysis of ethyl (+/-)-2-methylbutyrate with aliphatic amines is achieved using CC and PS lipases as catalysts.