Polysubstituted furans were prepared in moderate to good yields from various sulfur ylides and alkyl acetylenic carboxylates. The direct reactions of dimethylsulfonium acylmethylides with dialkyl acetylenedicarboxylates afforded dialkyl furan-3,4-dicarboxylates through a tandem sequence of Michael addition, intramolecular nucleophilic addition, 4π ring opening, intramolecular Michael addition, and elimination. The method was extended to synthesize furan-3-carboxylate, -2,4-dicarboxylates, and -2,3,4-tricarboxylates as well. The current method provides a direct and simple strategy in the synthesis of structurally diverse polysubstituted furans with mono to tricarboxylate groups from safe and readily available dimethylsulfonium acylmethylides and different alkyl acetylenic carboxylates.
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| http://dx.doi.org/10.1039/c9ra03563j | DOI Listing |
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