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Título: | Synthesis of chiral β-iodo-and vinylorganophosphorus(V) compounds by fragmentation of carbohydrate anomeric alkoxyl radicals |
Autor: | Hernández-Guerra, Daniel CSIC; Rodríguez Morales, María S. CSIC ORCID ; Suárez, Ernesto CSIC ORCID | Fecha de publicación: | 9-ene-2013 | Editor: | American Chemical Society | Citación: | Organic Letters 15(2): 250-253 (2013) | Resumen: | A 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. | Versión del editor: | https://pubs.acs.org/doi/10.1021/ol302939z | URI: | http://hdl.handle.net/10261/178851 | DOI: | 10.1021/ol302939z | Identificadores: | doi: 10.1021/ol302939z issn: 1523-7060 e-issn: 1523-7052 |
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