Collect. Czech. Chem. Commun. 2003, 68, 1319-1325

Synthesis of Homochiral Acyclic Mono- and Bis(α-amino acid)s with Oligo(oxyethylene) Chains

Martin Bělohradský, Luděk Ridvan and Jiří Závada*

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague, Czech Republic


Synthesis of homochiral α-amino acids 3a-3e and bis(α-amino acid)s 4a-4e via BF3·Et2O-catalyzed ring-opening of methyl (S)-1-[(benzyloxy)carbonyl]aziridine-2-carboxylate (7) with oligo(ethylene glycol)s and subsequent acid hydrolysis is reported.

Keywords: Amino acids; Oligo(ethylene glycol)s; Aziridines; Nucleophilic ring-opening reaction; Podands; Crown ethers.

References: 9 live references.