Synthesis of novel sila-substituted beta-amino acids

A highly efficient and stereoselective synthesis of unnatural cyclic sila-substituted P-amino acids has been developed from simple starting materials. The key step is nucleophilic ring opening of an intermediate aziridine with an umpolung synthon for the carboxylate anion. Functional group manipulation and deprotection reactions allow access to the desired trans beta-amino acids. (C) 2002 Elsevier Science Ltd. All rights reserved.