Alkylidene Meldrum's Acids as Platforms for the Vinylogous Synthesis of Dihydropyranones
Résumé
Upon Brønsted 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 to furnish an unprecedented route to 3,6dihydropyran-2-ones 5 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.
Origine | Fichiers produits par l'(les) auteur(s) |
---|