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

AutorFrancisco, Cosme G. ; Herrera, Antonio J. ; Suárez, Ernesto
Fecha de publicación21-sep-2002
EditorAmerican Chemical Society
CitaciónJournal of Organic Chemistry 67(21): 7439-7445 (2002)
ResumenThe reaction of specifically protected anhydroalditols with (diacetoxyiodo)benzene or iodosylbenzene and iodine is a mild and selective procedure for the synthesis of chiral 6,8-dioxabicyclo[3.2.1]octane and 2,7-dioxabicyclo[2.2.1]heptane ring systems under neutral conditions. This reaction can be considered to be an intramolecular glycosidation that goes through an intramolecular hydrogen abstraction promoted by an alkoxy radical followed by oxidation of the transient C-radical intermediate to an oxycarbenium ion. This methodology is useful not only for the preparation of chiral synthons but also for the selective oxidation of specific carbons of the carbohydrate skeleton, constituting a good procedure for the synthesis of protected uloses.
Descripción7 pages, 2 tables, 3 schemes.-- PMID: 12375977 [PubMed].-- Printed version published Oct 18, 2002.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo026004z
Versión del editorhttp://dx.doi.org/10.1021/jo026004z
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