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Diastereoselective synthesis of 2-aryl-3-vinyl-2,3-dihydrobenzo[b]furans through a Sakurai reaction: a mechanistic proposal
Authors:Jiménez-González Leticia  García-Muñoz Sergio  Alvarez-Corral Miriam  Muñoz-Dorado Manuel  Rodríguez-García Ignacio
Affiliation:Dpt. Química Orgánica, Universidad de Almería, 04120 Almería, Spain.
Abstract:The condensation of 2,3-dihydrobenzoxasilepins with aromatic aldehydes in the presence of boron trifluoride to form 2,3-dihydrobenzofurans shows a level of diastereoselection which is a function of the electronic nature of the aldehyde and the polarity of the solvent. The study of the mechanism of the reaction demonstrated that it proceeds through a ring-opened allylfluorosilane, which is stable enough to be isolated and characterized.
Keywords:aldehydes  allylation  diastereoselectivity  heterocycles  silanes
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