Patnam Ramesh, Juarez-Ruiz Juan M, Roy René
Department of Chemistry, Université du Québec à Montréal, Succ. Centre-Ville, Canada.
Org Lett. 2006 Jun 22;8(13):2691-4. doi: 10.1021/ol060671n.
[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.
[反应:见正文] 在阳离子铱(I)催化剂[(Ph(2)MeP)(2)Ir(cod)PF(6)]存在下,C-烯丙基糖苷立体选择性异构化为(E)-C-乙烯基糖苷或(Z)-外型-glycals。异构化产物受相对的1,2-立体化学关系和保护基团性质的影响。结合合理的反应机理对这些影响进行了讨论。