title: Catalytic, one-pot synthesis of beta-amino acids from alpha-amino acids. Preparation of alpha,beta-peptide derivatives.
abstract: The one-pot conversion of readily available alpha-amino acid into beta-amino acid derivatives was carried out in good yields. The method is a sequential process initiated by a tandem radical decarboxylation-oxidation reaction; the resulting acyliminium ion was trapped by silyl ketenes. Stoichiometric and catalytic versions of this reaction were developed and then applied to prepare modified di- and tripeptides. Interestingly, some tripeptides formed expanded beta-turns in the solid state.
authors.affiliation: Instituto de Productos Naturales y Agrobiología del CSIC, Avda. Astrofísico Francisco Sánchez 3, 38206-La Laguna, Tenerife, Spain.
authors.forename: Carlos
authors.initials: C
authors.lastname: Saavedra
authors.forename: Rosendo
authors.initials: R
authors.lastname: Hernández
authors.forename: Alicia
authors.initials: A
authors.lastname: Boto
authors.forename: Eleuterio
authors.initials: E
authors.lastname: Alvarez
mesh_terms: D002384:Catalysis; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D009842:Oligopeptides