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Title

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

AuthorsFrancisco, Cosme G. CSIC; Herrera, Antonio J. CSIC ; Suárez, Ernesto CSIC ORCID
Issue Date21-Sep-2002
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 67(21): 7439-7445 (2002)
AbstractThe 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.
Description7 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
Publisher version (URL)http://dx.doi.org/10.1021/jo026004z
URIhttp://hdl.handle.net/10261/16758
DOI10.1021/jo026004z
ISSN0022-3263
Appears in Collections:(IPNA) Artículos

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