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

JiménezGonzález Leticia | Zendy; GarcíaMuñoz Sergio | Zendy; ÁlvarezCorral Miriam | Zendy; MuñozDorado Manuel | Zendy; RodríguezGarcía Ignacio | Zendy

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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.

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