Carrillo Arregui, JokinCosta i Arnau, Anna M.Sidera Portela, MireiaVilarrasa i Llorens, Jaume2013-09-032013-09-0320110040-4039https://hdl.handle.net/2445/45524A practical solution to the formation of mixtures of E/Z and open/cyclic isomers in the reaction of (2R,4S)-4-hydroxy-2-methylpentanal (as its hemiacetal, a lactol) with conjugated phosphoranes (stabilised Wittig reagents) and Horner-Wadsworth-Emmons reagents is disclosed. The HWE reaction has a strong bias to give oxolanes. On the other hand, stabilised Wittig reagents give unsaturated carboxyl derivatives of configuration E (major) and oxolanes (minor); the latter can be avoided by addition of CF3CH2OH or using morpholine amide phosphorane.5 p.application/pdfeng(c) Elsevier Ltd, 2011Química orgànicaReactivitat (Química)Nomenclatura químicaSíntesi orgànicaOrganic chemistryReactivity (Chemistry)Chemical nomenclatureOrganic synthesisinfo:eu-repo/semantics/article5988622013-09-03info:eu-repo/semantics/openAccess