Sterically Controlled Syntheses of Optically Active Organic Compounds. XIX. Asymmetric Syntheses of Amino Acids by the Strecker Reaction

The Strecker type syntheses of optically active alanine, butyrine, valine, and leucine by the use of the corresponding aldehydes, hydrogen cyanide, and optically active α-alkylbenzylamines and α-(1-naphthyl)ethylamine were carried out (reaction A). The optical purities were in the range 22–51%. The modified Strecker type syntheses of alanine from acetaldehyde cyanohydrine and optically active amines were also carried out (reaction B). The optical purities of alanine were in the range 44–48%. In reaction B, optically active phenylglycine was also used as an amino source. The optical purities of the synthesized alanine were in the range 12–17%.