Diastereoselective synthesis of 2-aryl-3-vinyl-2,3-dihydrobenzo[b]furans through a Sakurai reaction: a mechanistic proposal.
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.
Jiménez-González
Leticia
L
Dpt. Química Orgánica, Universidad de Almería, 04120 Almería, Spain.
García-Muñoz
Sergio
S
Alvarez-Corral
Miriam
M
Muñoz-Dorado
Manuel
M
Rodríguez-García
Ignacio
I