Catalytic, one-pot synthesis of beta-amino acids from alpha-amino acids. Preparation of alpha,beta-peptide derivatives.
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.
Saavedra
Carlos
C
Instituto de Productos Naturales y Agrobiología del CSIC, Avda. Astrofísico Francisco Sánchez 3, 38206-La Laguna, Tenerife, Spain.
Hernández
Rosendo
R
Boto
Alicia
A
Alvarez
Eleuterio
E
D002384:Catalysis; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D009842:Oligopeptides