PREPARATIVE BIOORGANIC CHEMISTRY .12. ENZYMATIC PREPARATION OF THE ENANTIOMERS OF SOME 1-PHENYL-1-ALKANOLS

The acetates of racemic 1-phenyl-1-heptanol, 1-phenyl-1-octanol and 1-phenyl-1-nonanol were hydrolyzed by Pseudomonas lipase in 10% acetone-0.1 M phosphate buffer (pH 6.9) at 30°C. Due to remarkable differences in the rates of hydrolysis of the enantiomeric acetates, the reaction led to (R)-(+)-alcohols (92.2-97.8% e.e.)_and (S)-(-)-acetates (99.6-100.0% e.e.). Slow reverse esterification of 1-phenyl-1-octanol took place in the presence of 1 equivalent of acetic acid. Addition of ethyl acetate markedly increased the rate of esterification of give (R)-(+)-phenyloctyl acetate (92.8% e.e.). Attempts to esterify racemic alcohols in organic solvents were unsuccessful because of low reaction rate and/or low enantioselectivity. © 1990.