Sterically Controlled Syntheses of Optically Active Organic Compounds. XVII. Asymmetric Syntheses of Amino Acids by Addition of Benzoyl Cyanide to the Azomethine Compounds

The addition reactions of benzoyl cyanide to the Schiff’s bases prepared from several aliphatic aldehydes with optically active benzylic amines were studied. The adioditn products were hydrolyzed and hydrogenolyzed to form optically active amino acids. The synthetic yields of optically active amino acids were in a range 15 to 57% and the optical purities were in a range 15–37%. When S-α-alkylbenzylamines were used, S-amino acids were obtained.