The enzymatic resolution of racemic phenylglycine, phenylglycinol and
phenylalaninol has been studied in organic solvents under a variety of
experimental conditions. Subtilisin in 3-methyl-3-pentanol was effect
ive for the resolution of phenylglycine esters, via N-acylation with t
rifluoroethyl butyrate. Porcine pancreatic lipase in ethyl acetate gav
e satisfactory results in the resolution of phenylglycinol and phenyla
laninol; the alpha or beta position of the phenyl group was found to i
nfluence both the rate and the chemioselectivity of the reaction.