Competitive parallel reactions with opposite enantioselectivity are pr
esented as a strategy to enhance the enantiomeric product purity in en
zymatic kinetic resolution. Lipase-catalyzed simultaneous hydrolysis a
nd amidation of racemic methy 12-chloropropionate led to significantly
improved amide yield and enantiomeric excess. Process results can be
controlled by changing the hydrolysis/amidation reaction rates through
variation of the solvent and the initial amine concentration. This is
described by a kinetic model.