Abstract
An efficient, one-pot tandem reaction of pyridine, an α-haloacetate,
an aromatic aldehyde and cyclohexane-1,3-dione, dimedone or 4-hydrocoumarin
in acetonitrile using 1,4-diazabicyclo[2.2.2]octane
as a basic catalyst is described. The products, 2,3,6,7-tetrahydro-4(5H )-benzofuranones and 2,3-dihydrofurocoumarins,
are obtained in a diastereoselective manner via a mechanism involving
in situ formation of a pyridinium ylide. ¹ H
NMR spectroscopy and single crystal X-ray analysis indicates that
the products are formed exclusively as the trans isomers.
Key words
tandem reaction - pyridinium ylide - benzofuranone - furocoumarin - diastereoselective
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