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Catalytic, One-Pot Synthesis of β-Amino Acids from α-Amino Acids. Preparation of α,β-Peptide Derivatives

AuthorsSaavedra, Carlos Javier ; Hernández, Rosendo ; Boto, Alicia ; Álvarez, Eleuterio
Molecular structure
Issue Date24-Apr-2009
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 74(13): 4655-4665 (2009)
AbstractThe 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.
Description11 páginas, 2 figuras, 6 tablas, 3 esquemas.
Publisher version (URL)http://dx.doi.org/10.1021/jo9004487
Appears in Collections:(IPNA) Artículos
(IIQ) Artículos
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