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

Authors:Francisco, Cosme G.
González Martín, Concepción C.
Herrera, Antonio J.
Rodríguez Paz, Nieves
Suárez, Ernesto
Issue Date:7-Nov-2006
Publisher:Elsevier
Citation:Tetrahedron Letters 47(51): 9057-9060 (2006)
Abstract:The 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.
Description:4 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
URI:http://hdl.handle.net/10261/13657
ISSN:0040-4039
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Appears in Collections:(IPNA) Artículos

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