Synthesis of α-Amino Acids by Ring Opening of Aziridine-2-carboxylates with Carbon Nucleophiles

Article abstract of DOI:10.1016/0040-4039(94)02198-K

Excellent regiospecificity has been achieved in the reaction of carbon nucleophiles with N-para-toluenesulfonylaziridine-2-carboxylic acid (6, R=H) protected as the anion.This has been developed into a general and high yielding synthesis of optically pure α-amino acids containing one chiral centre.When the aziridine (20) containing a second chiral centre was used, only lithium trimethylsilylacetylide gave the desired α-amino acid.Reaction with higher order cuprates gave lower yields, the principal products being the protected β-amino acids (22) and (23).