Diastereoselective Synthesis of 2??Aryl??3??vinyl??2, 3??dihydrobenzo [b] furans through a Sakurai Reaction: A Mechanistic Proposal

L Jiménez??González, S García??Muñoz…

Index: Jimenez-Gonzalez, Leticia; Garcia-Munoz, Sergio; Alvarez-Corral, Miriam; Munoz-Dorado, Manuel; Rodriguez-Garcia, Ignacio Chemistry - A European Journal, 2007 , vol. 13, # 2 p. 557 - 568

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Citation Number: 17

Abstract

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 ...