β3-Amino acids by nucleophilic ring-opening of N-nosyl aziridines

N-Nosyl aziridines can be easily prepared from 1,2-amino alcohols derived from α-amino acids. Nucleophilic ring-opening of N-nosyl aziridines with cyanide ions followed by hydrolysis of the corresponding nitriles lead to N-nosyl β3-amino acids, which can be readily converted into a variety of derivatives bearing adequate functionality for peptide synthesis. The proposed methodology is simple, efficient, and amenable to large-scale preparations.