A Method for the Preparation of Stereochemically Defined ψ Pseudodipeptides

Article abstract of DOI:10.1021/jo00379a019

A short, stereochemically defined synthesis of (2S,5S)-ψ pseudodipeptides (7a,7b,10) using commercially available, chiral amino acids has been developed.The key step of the synthesis is the intramolecular S_N2 displacement of bromine with alkoxide to give 1,4-oxazin-2-ones (6a,6b,9) that are subsequently hydrolyzed to the desired ψ pseudodipeptides.