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Título

Synthesis of unnatural amino acids from serine derivatives by β-fragmentation of primary alkoxyl radicals

AutorBoto, Alicia ; Gallardo, Juan Antonio ; Hernández, Dácil ; Hernández, Rosendo
Fecha de publicación15-ago-2007
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 72(19): 7260-7269 (2007)
ResumenThe fragmentation of primary alkoxyl radicals has been scarcely used in synthesis since other competing processes (such as oxidation or hydrogen abstraction) usually predominate. However, when serine derivatives were used as substrates, the scission took place in excellent yields. Tandem scission−allylation, −alkylation, or −arylation reactions were subsequently developed. This one-pot methodology was applied to the synthesis of unnatural amino acids, which are useful synthetic blocks or amino acid surrogates in peptidomimetics.
Descripción10 pages, 3 tables, 2 schemes.-- Printed version published Sep 14, 2007.
Supporting information (1H and 13C NMR spectra, 52 pages) available at: http://pubs.acs.org/doi/suppl/10.1021/jo071155t
Versión del editorhttp://dx.doi.org/10.1021/jo071155t
URIhttp://hdl.handle.net/10261/12982
DOI10.1021/jo071155t
ISSN0022-3263
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