Enantioselective synthesis of α-amino acids from glycine t-butyl ester

Article abstract of DOI:10.1016/S0040-4020(97)00372-4

Enantioselective syntheses of optically active α-amino acids from glycine t-butyl ester through Schiff base employing (+)-N-alkyl-10-camphorsulfonamides as chiral auxiliaries were described. Methylation of Schiff base 5 gave high asymmetric inductions, whereas ethylation, allylation and benzylation gave fair asymmetric inductions. The stereochemistry of the major alkylation product was S configuration at the newly formed stereogenic center with the exception of the benzylation reaction in which the R configuration was generated.