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Title

Stereoselective Synthesis of C-Ketosides by Sequential Intramolecular Hydrogen Atom Transfer-Intermolecular Allylation Reaction

AuthorsMartín, Ángeles CSIC ORCID ; Pérez-Martín, Inés CSIC ORCID ; Quintanal, Luis M.; Suárez, Ernesto CSIC ORCID
KeywordsC-Ketoside
Radical reaction
Hydrogen transfer
Allylation
Tandem
Issue Date19-Jun-2008
PublisherElsevier
CitationTetrahedron Letters 49(35): 5179-5181 (2008)
AbstractA tandem 1,5 or 1,6 hydrogen atom transfer (HAT)–radical allylation using carbohydrate models is described. The HAT reaction generated a C-glycos-1-yl radical intermediate, which added to allyltri-n-butyltin with high diastereoselectivity, to give C-ketosides with the quaternary carbon carrying two differently functionalized tethers.
Description3 pages, 1 table, 2 schemes.-- Printed version published Aug 25, 2008.
Supporting information (16 pages) available at: http://dx.doi.org/10.1016/j.tetlet.2008.06.070
Publisher version (URL)http://dx.doi.org/10.1016/j.tetlet.2008.06.070
URIhttp://hdl.handle.net/10261/12614
DOI10.1016/j.tetlet.2008.06.070
ISSN0040-4039
Appears in Collections:(IPNA) Artículos




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