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Diastereoselective Synthesis of 2‐Aryl‐3‐vinyl‐2,3‐dihydrobenzo[ b ]furans through a Sakurai Reaction: A Mechanistic Proposal
Author(s) -
JiménezGonzález Leticia,
GarcíaMuñoz Sergio,
ÁlvarezCorral Miriam,
MuñozDorado Manuel,
RodríguezGarcía Ignacio
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601017
Subject(s) - boron trifluoride , aldehyde , solvent polarity , aryl , chemistry , polarity (international relations) , ring (chemistry) , condensation , medicinal chemistry , solvent , condensation reaction , reaction mechanism , organic chemistry , catalysis , physics , biochemistry , alkyl , thermodynamics , cell
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.