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Title

Fragmentation of carbohydrate anomeric alkoxy radicals: a new synthesis of chiral 1-halo-1-iodo alditols

AuthorsGonzález Martín, Concepción C. ; Kennedy, Alan R.; León, Elisa I. ; Riesco-Fagundo, Concepción ; Suárez, Ernesto
KeywordsHalogen compounds
Alditols
Carbohydrates
Iodine
Radical reactions
Issue Date5-Dec-2003
PublisherJohn Wiley & Sons
CitationChemistry - A European Journal 9(23): 5800-5809 (2003)
AbstractTreatment of 1,2-fluorohydrins, 1,2-chlorohydrins, 1,2-bromohydrins, and 1,2-iodohydrins of the D-gluco, D-galacto, D-lacto, L-rhamno, D-allo, L-arabino, 3-deoxy-D-gluco, and 3,4-dideoxy-D-gluco families of carbohydrates with the (diacetoxyiodo)benzene/iodine system afforded 1-fluoro-1-iodo, 1-chloro-1-iodo, 1-bromo-1-iodo, and 1,1-diiodo alditols, respectively, in excellent yields. The reaction was achieved by radical fragmentation of the C1bond;C2 bond, triggered by the initially formed anomeric alkoxy radical, and subsequent trapping of the C2-radical by iodine atoms. This methodology is compatible with the stability of the protective groups most frequently used in carbohydrate chemistry. The potential utility of these 1-halo-1-iodo alditols as chiral synthons was evaluated by their transformation into alk-1-enyl iodides and in the Takai E-olefination reaction.
Description10 pages, 3 tables, 2 schemes.-- PMID: 14673851 [PubMed].-- Supporting information (52-page PDF file) available at: http://www.wiley-vch.de/contents/jc_2111/2003/f5294_s.pdf
Publisher version (URL)http://dx.doi.org/10.1002/chem.200305294
URIhttp://hdl.handle.net/10261/16755
DOI10.1002/chem.200305294
ISSN0947-6539
Appears in Collections:(IPNA) Artículos
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