Subtle stereochemical and electronic effects in iridium-catalyzed isomerization of C-allyl glycosides.
[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.
Patnam
Ramesh
R
Department of Chemistry, Université du Québec à Montréal, Succ. Centre-Ville, Canada.
Juarez-Ruiz
Juan M
JM
Roy
René
R
D002384:Catalysis; D006027:Glycosides / Q000737:chemistry*; D007495:Iridium / Q000737:chemistry*; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
D006027:Glycosides; D009005:Monosaccharides; D014753:Vinyl Compounds; D007495:Iridium; D010165:Palladium