A new synthesis of α-methylserine by nucleophilic ring-opening of N-sulfonyl aziridines

Article abstract of DOI:10.1016/0040-4039(95)00621-I

Conversion of tritylated 2-methylglycidol to the corresponding aziridine occurs by Staudinger cyclization of the intermediate azido alcohol. After N-sulfonylation with Ses-Cl and ring-opening with benzyl alcohol, oxidation of the primary alcohol provides. N,O-bisprotected α-methylserine directly suitable for repetitive peptide synthesis. This sequence represents a general enantioselective protocol for the synthesis of α-methylserine and other α,α-disubstituted amino acids.