beta(3)-amino acids by nucleophilic ring-opening of N-nosyl aziridines

N-Nosyl aziridines can be easily prepared from 1,2-amino alcohols derived f rom a-amino acids. Nucleophilic ring-opening of N-nosyl aziridines with cya nide ions followed by hydrolysis of the corresponding nitriles lead to N-no syl beta (3)-amino acids, which can be readily converted into a variety of derivatives bearing adequate functionality for peptide synthesis. The propo sed methodology is simple, efficient, and amenable to large-scale preparati ons. (C) 2001 Elsevier Science Ltd. All rights reserved.