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Synthesis of highly functionalized chiral nitriles by radical fragmentation of beta-hydroxy azides. Convenient transformation of aldononitriles into 1,4- and 1,5-iminoalditols

AutorHernández, Rosendo ; León, Elisa I. ; Moreno, Pilar ; Riesco-Fagundo, Concepción ; Suárez, Ernesto
Fecha de publicación5-nov-2004
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 69(24): 8437-8444 (2004)
ResumenThe synthesis of highly functionalized nitriles by an alkoxyl radical fragmentation of cyclic β-hydroxy azides is described. The alkoxyl radicals were generated by reaction of the alcohols with (diacetoxyiodo)benzene and iodine under mild conditions compatible with the presence of sensitive substituents and the protective groups most frequently used in carbohydrate chemistry. To explore the scope and limitations of this methodology, experiments were carried out using a variety of β-hydroxy azides of the carbohydrate (1−6, 33, and 41), monoterpenoid (21 and 22), and steroid (23−25) families of natural products. Of special interest are the aldopentonitriles (15−18, 34, and 42) and aldotetrononitriles (19 and 20) synthesized from the corresponding 2-azido-2-deoxycarbohydrates. To demonstrate the versatility of these aldononitriles as chiral synthons, 1,4-imino-1-deoxysugar (37) and 1,5-imino-1-deoxysugar (43) analogues of the polyhydroxypyrrolidine and -piperidine types were prepared.
Descripción8 pages, 2 tables, 5 schemes.-- PMID: 15549818 [PubMed].-- Printed version published Nov 26, 2004.
Supporting information available: Detailed experimental procedures and spectral and analytical data for several compounds.-- Available at: http://pubs.acs.org/doi/suppl/10.1021/jo049026p
Versión del editorhttp://dx.doi.org/10.1021/jo049026p
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