Reaction of benzaldehyde, chloroform, RNH2 (R = DL-PhCHMe, (R)-(+)-PhCHMe, (S)-(-)-PhCHMe), and solid potassium hydroxide was carried out in anhydrous acetonitrile at -5-0癈, with tetra-Bu ammonium bromide as phase transfer catalyst. The reaction products I were hydrolyzed and hydrogenolyzed to yield the corresponding optically active phenylglycine. I (R = DL-CHPhMe) could be also obtained by reaction of 1-phenyl-2,2,2-trichloroethanol with DL-PhCHMeNH2. The reaction mechanism was discussed.

Key words: PHENYLETHYLAMINE P, HYDROLYSIS, BENZENE P, CHLOROFORM, PHASE TRANSFER CATALYSIS, BENZALDEHYDE, GLYCINE, CHIRALITY, HYDROGENOLYSIS, INDUCTIVE EFFECT