Alkylidene Meldrum's Acids as Platforms for the Vinylogous Synthesis of Dihydropyranones

Upon Bronsted base organocatalysis, ketone-derived alkylidene Meldrum's acids proved to be competent vinylogous platforms able to undergo a formal (4+2) cycloaddition reaction with dihydro-2,3-furandione, providing an unprecedented route to 3,6-dihydropyran-2-ones as spiro[4.5]decane derivatives with up to 98 % ee thanks to the commercially available Takemoto catalyst. Preliminary investigation showed that this reaction could be extended to other activated ketones, establishing these alkylidene Meldrum's acids as a novel C4-synthon in the vinylogous series.

Automated summary

Through Bronsted base organocatalysis, ketone-derived alkylidene Meldrum's acids react with dihydro-2,3-furandione in a formal (4+2) cycloaddition reaction, yielding 3,6-dihydropyran-2-ones with up to 98% ee. This reaction can be extended to other activated ketones, making alkylidene Meldrum's acids a novel C4-synthon in the vinylogous series.