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Chemoselective 1-ethylpiperidine hypophosphite (EPHP)-mediated intermolecular radical additions of 1-deoxy-1-halo-1-iodo-alditols to electron-deficient olefins

AuthorsFrancisco, Cosme G. ; González Martín, Concepción C. ; Herrera, Antonio J. ; Rodríguez Paz, Nieves ; Suárez, Ernesto
Issue Date7-Nov-2006
CitationTetrahedron Letters 47(51): 9057-9060 (2006)
AbstractThe chemoselective radical reduction of the iodine atom in a series of 1-deoxy-1-halo-1-iodo-alditols with the 1-ethylpiperidine hypophosphite (EPHP)/AIBN system is described. EPHP is also a good chain carrier for the radical addition of gem-dihalocompounds to electron-deficient olefins. Thus, the synthesis of 4-halo-glycooctononitriles and 4-halo-glycoheptononitriles can be achieved by an intermolecular addition of the 1-deoxy-1-halo-alditol-1-yl radical intermediate to acrylonitrile.
Description4 pages, 2 tables, 1 scheme.-- Printed version published Dec 18, 2006.-- Supporting information (33 pages Word file) available at: http://dx.doi.org/10.1016/j.tetlet.2006.10.086
Publisher version (URL)http://dx.doi.org/10.1016/j.tetlet.2006.10.086
Appears in Collections:(IPNA) Artículos
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