Subtle stereochemical and electronic effects in iridium-catalyzed isomerization of C-allyl glycosides |
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Authors: | Patnam Ramesh Juarez-Ruiz Juan M Roy René |
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Affiliation: | Department of Chemistry, Université du Québec à Montréal, Succ. Centre-Ville, Canada. |
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Abstract: | [reaction: see text] Stereoselective isomerization of C-allyl glycosides into (E)-C-vinyl glycosides or (Z)-exo-glycals was carried out in the presence of the cationic iridium(I) catalyst [(Ph(2)MeP)(2)Ir(cod)PF(6)]. The products of the isomerization were affected by the relative 1,2-stereochemical relationships and by the nature of the protecting groups. These effects are discussed along with a plausible reaction mechanism. |
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