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dc.contributor.authorFrancisco, Cosme G.en_US
dc.contributor.authorGonzález Martín, Concepción C.en_US
dc.contributor.authorKennedy, Alan R.en_US
dc.contributor.authorRodríguez Paz, Nievesen_US
dc.contributor.authorSuárez, Ernestoen_US
dc.date.accessioned2009-04-28T07:18:34Z-
dc.date.available2009-04-28T07:18:34Z-
dc.date.issued2008-06-23en_US
dc.identifier.citationChemistry - A European Journal 14(22): 6704-6712 (2008)en_US
dc.identifier.issn0947-6539-
dc.identifier.urihttp://hdl.handle.net/10261/12620-
dc.description9 pages, 1 figure, 1 table, 3 schemes.-- PMID: 18576400 [PubMed].-
dc.descriptionSupporting information (30 pages) available at: http://www.wiley-vch.de/contents/jc_2111/2008/f800734_s.pdf-
dc.description2 Errata to this paper (1 page) published in: [1] Chemistry - A European Journal 14(33): 10179 (2008), http://dx.doi.org/10.1002/chem.200890136, and [2] Chemistry - A European Journal 14(35): 10871 (2008), http://dx.doi.org/10.1002/chem.200890145-
dc.description.abstractA new general methodology for the synthesis of 1,1,1-trihaloalditols by starting from 1,5-anhydro-2-deoxy-hex-1-enitol derivatives (glycals) is described. The halogens are introduced sequentially in each of the three different steps of the process. The fluorine is introduced in the first step by electrophilic fluorination of the starting glycal; next, hydroxyhalogenation of the resulting vinyl fluoride allows the addition of any halogen (F, Cl, Br or I) at will, and finally, an iodine atom is inserted through an alkoxyl radical fragmentation reaction. This methodology allows the preparation of diverse types of 1,1,1-trihalogenated compounds (R--CF(2)I, R--CFI(2), R--CFClI and R--CFBrI) under mild conditions compatible with sensitive substituents. In some cases, the diastereomeric mixtures generated from R--CFClI and R--CFBrI can be chromatographically separated, and their configuration determined by X-ray crystallographic analysis. The synthetic usefulness of these compounds has been preliminarily assessed by examining the reactivity of the fluorinated radical generated by rupture of the C--I bond.-
dc.description.sponsorshipThis work was supported by the Investigation programs nos. CTQ2004–06381/BQU, CTQ2004–02367/BQU and CTQ2007–67492/BQU of the Ministerio de Educación y Ciencia (Spain) cofinanced with the Fondo Europeo de Desarrollo Regional (FEDER). N.R.P. thanks the I3P-CSIC Program for a fellowship.-
dc.format.extent2373 bytes-
dc.format.extent370976 bytes-
dc.format.mimetypetext/plain-
dc.format.mimetypeapplication/pdf-
dc.language.isoengen_US
dc.publisherJohn Wiley & Sons-
dc.rightsclosedAccessen_US
dc.subjectAlditols-
dc.subjectAsymmetric synthesis-
dc.subjectCarbohydrates-
dc.subjectHalogens-
dc.subjectRadical reactions-
dc.titleFragmentation of carbohydrate anomeric alkoxyl radicals: new synthesis of chiral 1-fluoro-1-halo-1-iodoalditolsen_US
dc.typeartículoen_US
dc.identifier.doi10.1002/chem.200800734-
dc.relation.publisherversionhttp://dx.doi.org/10.1002/chem.200800734-
dc.contributor.funderMinisterio de Educación y Ciencia (España)-
dc.contributor.funderEuropean Commission-
dc.contributor.funderConsejo Superior de Investigaciones Científicas (España)-
dc.identifier.funderhttp://dx.doi.org/10.13039/501100000780es_ES
dc.identifier.funderhttp://dx.doi.org/10.13039/501100003339es_ES
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