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Título

Radical Fragmentation of β-Hydroxy Azides. Synthesis of Chiral Nitriles

AutorHernández, Rosendo ; León, Elisa I. ; Moreno, Pilar ; Suárez, Ernesto
Fecha de publicación26-dic-1997
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 62(26): 8974-8975 (1997)
ResumenIn previous papers, we have described the preparation of chiral building blocks by fragmentation of anomeric alkoxy radicals of carbohydrates. Moreover, nitriles have proven to be extremely versatile functional groups. They may undergo a variety of reactions, especially reduction, alkylation of their enolates, enzymatic hydrolysis to acids and amides by nitrile hydratase, Ritter reaction, and many other synthetically useful transformations.
In this paper, we develop a new protocol for the synthesis of nitriles by β-fragmentation of alkoxy radicals by reaction of β-hydroxy azides with (diacetoxyiodo)benzene (DIB) and iodine. In particular, this reaction has been applied to the synthesis of chiral nitriles by β-fragmentation of anomeric alkoxy radicals from 2-azido-2-deoxy sugars, as shown in Scheme 1.
Descripción2 pages, 1 table, 2 schemes.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo971836w
Versión del editorhttp://dx.doi.org/10.1021/jo971836w
URIhttp://hdl.handle.net/10261/17237
DOI10.1021/jo971836w
ISSN0022-3263
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