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Synthesis of chiral β-iodo-and vinylorganophosphorus(V) compounds by fragmentation of carbohydrate anomeric alkoxyl radicals

AuthorsHernández-Guerra, Daniel ; Rodríguez Morales, María S. ; Suárez, Ernesto
Issue Date9-Jan-2013
PublisherAmerican Chemical Society
CitationOrganic Letters 15(2): 250-253 (2013)
AbstractA new general methodology for the synthesis of chiral vinylphosphonate and vinylphosphine oxide carbohydrate derivatives has been developed using the anomeric alkoxyl radical fragmentation reaction as the key step. The synthetic sequence proceeded via β-iodophosphonate and β-iodophosphine oxide intermediates, which may be interesting synthons for the introduction of phosphorus into organic molecules. These vinylphosphonates could be easily transformed into 2-methylene-1-phosphapentofuranoses (3-methylene-1,2-oxaphospholanes) and β-aminophosphonates, isosteres of biologically active α-methylene-γ-lactones and β-amino acids, respectively.
Publisher version (URL)https://pubs.acs.org/doi/10.1021/ol302939z
Identifiersdoi: 10.1021/ol302939z
issn: 1523-7060
e-issn: 1523-7052
Appears in Collections:(IPNA) Artículos
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