Highly selective enzymatic kinetic resolution of primary amines at 80 degrees C: a comparative study of carboxylic acids and their ethyl esters as acyl donors

Optimization of the kinetic resolution of 2-amino-4-phenyl-butane was achieved at 80 degrees C using CAL-B-catalyzed aminolysis of carboxylic acids and their ethyl esters. The reactions carried out with long chain esters and the corresponding acids as acyl donors proceeded with remarkably high enantioselectivity. The use of carboxylic acids as acylating agents led to a marked acceleration of the reaction rate compared to their ester counterparts. Lauric acid led to enantiomeric excesses superior to 99.5% for both the remaining amine and the corresponding lauramide at 50% conversion (reached in 3 h). These optimized conditions were applied to the resolution of a series of aliphatic and benzylic amines.