Different primary alcohols were transesterified using Mucor meihei lipase. 2,3-Butanedione monoxime acrylate was used efficiently as an acrylating agent to synthesize optically active acrylates. The effects of substrate substitution and solvent on the reaction rate were studied. The results showed that the reaction rates in nonpolar solvents were the fastest for acryloylating reactions reported until now. The enantiomeric excess (ee) and enantiomeric purity (E value) of all the acrylate monomers were evaluated and compared. The synthesized optically active acrylate monomers were polymerized by the free-radical initiation technique.