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Addition of secondary phosphines to a vinyl ether of diacetone-d-glucose: a new approach to optically active phosphines and their derivatives
Authors:Boris A Trofimov  Boris G Sukhov  Svetlana F Malysheva  Natal’ya A Belogorlova  Anatolii P Tantsirev  Lidiya N Parshina  Ludmila A Oparina  Sergey P Tunik  Nina K Gusarova
Institution:A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, Irkutsk 664033, Russia
Abstract:Secondary phosphines react readily with a vinyl ether of diacetone-d-glucose under radical initiation conditions to give, in high yield, anti-Markovnikov adducts, diorganyl{2-3-O-(1,2:5,6-di-O-isopropylidene)-d-glucofuranosyloxy]ethyl}phosphines, which oxidize almost quantitatively upon reacting with air oxygen or elemental sulfur to form the corresponding optically active phosphine oxides or sulfides.
Keywords:Secondary phosphines  d-glucose" target="_blank">Vinyl ether of diacetone-d-glucose  Addition  Radical initiation  Optically active tertiary phosphines  Phosphine oxides and sulfides
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