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A convenient and chemoselective one-pot oxidation/Wittig reaction for the C2-homologation of carbohydrate-derived glycols

AuthorsPinacho Crisóstomo, Fernando R. ; Carrillo Fumero, Romen ; Martín, Tomás ; García-Tellado, Fernando ; Martín, Víctor S.
Issue Date22-Oct-2005
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 70(24): 10099-10101 (2005)
AbstractA simple and convenient one-pot protocol for the chemoselective C2-homologation of carbohydrate-derived glycols is described. The method comprises the chemoselective oxidation of the glycol to the corresponding hydroxyaldehyde and the subsequent Wittig alkenylation. In addition, the method does not need selective protective group manipulation, and it is safe, economical, fast (5 to 6 h), and bench-friendly. Its general utility is discussed.
Description3 pages, 2 tables.-- PMID: 16292846 [PubMed].-- Printed version published Nov 25, 2005.
Supporting information available: Spectroscopic and analytical data for several compounds.-- Available at: http://pubs.acs.org/doi/suppl/10.1021/jo051566e
Erratum in: Journal of Organic Chemistry 71(3): 1288 (2006), doi: 10.1021/jo052606h.
Publisher version (URL)http://dx.doi.org/10.1021/jo051566e
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