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Catalytic, One-pot Synthesis Of Beta-amino Acids From Alpha-amino Acids. Preparation Of Alpha,beta-peptide Derivatives.

Carlos J Saavedra, R. Hernández, A. Boto, E. Álvarez
Published 2009 · Chemistry, Medicine

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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.



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