Palladium-Catalyzed Approach to Substituted Dihydrofurans, Cyclopenta[b]furans and Tetrahydrobenzofurans

Abstract

The reaction of a symmetrical allylic dicarbonate or diacetate with a variety of β-keto esters in the presence of a palladium catalyst gave 2-substituted 5-vinyl-4,5-dihydrofuran-3-carboxylates, 4,6a-dihydro-3aH-cyclopenta[b]furan-3-carboxylates, and 3a,4,5,7a-tetrahydrobenzofuran-3-carboxylates in moderate to good yields.

Key word

palladium catalyst - allylic substitution - tandem reaction - dihydrofuran - optical resolution

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11

According to our preliminary results, the corresponding chiral amides derived from either cyclic meso diacetate 3 or 5 with amide 8 were also separable on silica gel chromatography to afford diastereomerically pure (enantiomerically pure) dihydrofurans.