Novel Synthesis of 3-Substituted 2,3-Dihydrobenzofurans via ortho-Quinone Methide Intermediates Generated in Situ
Abdul kadar Shaikh and George Varvounis*
*Section of Organic Chemistry and Biochemistry, Department of
Chemistry, University of Ioannina, 451 10 Ioannina, Greece, Email: gvarvoun
cc.uoi.gr
A. k. Shaikh, G. Varvounis, Org. Lett., 2014, 16, 1478-1481.
DOI: 10.1021/ol500290e
Abstract
Fluoride-induced desilylation of 2-bromo-1-{2-[(triisopropylsilyl)oxy]phenyl}ethyl nitrate enables a regioselective one-pot synthesis of 3-substituted 2,3-dihydrobenzofurans via generation of o-quinone methides followed by Michael addition of different C, N, O, and S nucleophiles, and intramolecular 5-exo-tet elimination of a bromide anion. The method has potential synthetic applications in drug discovery.
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proposed mechanism
Key Words
ID: J54-Y2014
