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Intramolecular hydrogen abstraction reaction promoted by N-radicals in carbohydrates. Synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems

AutorFrancisco, Cosme G. ; Herrera, Antonio J. ; Suárez, Ernesto
Fecha de publicación14-ene-2003
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 68(3): 1012-1017 (2003)
ResumenThe reaction of phenyl and benzyl amidophosphates and alkyl and benzyl carbamate derivatives of aminoalditols with (diacetoxyiodo)benzene or iodosylbenzene and iodine is a mild and selective procedure for the synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems under neutral conditions. This reaction can be considered to be an intramolecular N-glycosidation that goes through an intramolecular 1,5-hydrogen abstraction promoted by an N-amido radical followed by oxidation of the transient C-radical intermediate to an oxycarbenium ion. This methodology proved to be useful not only as a suitable strategy for the preparation of these bicyclic arrays but also for the selective oxidation of specific carbons of the carbohydrate skeleton, constituting a good procedure for the synthesis of protected N,O-uloses.
Descripción6 pages, 2 tables, 3 schemes.-- PMID: 12558429 [PubMed].-- Printed version published Feb 7, 2003.
Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo026314h
Versión del editorhttp://dx.doi.org/10.1021/jo026314h
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