Synthesis of enantiopure (S)-α-hydroxy carboxanilides from (S)-α-amino acids

Article abstract of DOI:10.1055/s-1995-4080

α-Hydroxy carboxanilides 3 a-c were obtained without racemization in a synthetically simple way starting from the corresponding α-amino acids by diazotization and subsequent treatment of the sodium α-hydroxy carboxylates with anilinium chloride in moderate yields. The enantiopurity of 3a-c was easily determined by ¹H NMR spectroscopy of the diastereomeric O,O-acetals 5/6a-c derived from exo-lactol 4.