Lipase-catalyzed hydrolysis of some racemic 1-acetoxy-2-arylpropanes

Racemic 1-acetoxy-2-phenylpropane (12) and 1-acetoxy-2-(2-naphthyl)propane (33) were hydrolyzed with lipase at 35-36 degrees C for 2 and 24 h to give predominantly (S)-2-phenyl-1-propanol (11) and (S)-2-(2-naphthyl)-1-propanol (32), respectively. However, racemic 1-acetoxy-2-(1-naphthyl)propane (25) was recovered intact even when the reaction was carried out for 240 h. On the other hand, the enantioselectivities towards racemic 2-phenyl (16), 2-(p-tolyl) (20), 2-(1-naphthyl) (28), and 2-(2-naphthyl) (36) derivatives of 1-acetoxy-2-propanol were very low.