Diastereoselective Synthesis of trans-2,3,6,7-Tetrahydro-4(5H)-benzofuran­ones and trans-2,3-Dihydrofurocoumarins via Pyridinium Ylide Assisted Tandem Reactions

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. ^¹H 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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Crystallographic data for compounds 4a (CCDC 764133), 4f (CCDC 764134), 4j (CCDC 764136) and 4m (CCDC 764135) have been deposited at the Cambridge Crystallographic Data Centre.