5-Substituted-furan-2(3<i>H</i>)-ones in [8 + 2]-Cycloaddition with 8,8-Dicyanoheptafulvene
Marta Romaniszyn, Lesław Sieroń, Łukasz Albrecht
Abstract
This study demonstrates the use of organocatalytic Brønsted base activation of 5-substituted-furan-2(3H)-ones to generate 2π-components for the diastereoselective [8 + 2]-cycloaddition involving 8,8-dicyanoheptafulvene as an 8π-component. The use of dienolates in a higher-order cycloaddition reaction leads to the formation of biologically relevant polycyclic products bearing a γ-butyrolactone structural motif, thus broadening the synthetic potential of Brønsted base activated higher-order cycloadditions.
Topics & Concepts
CycloadditionChemistryFuranBrønsted–Lowry acid–base theoryStereochemistryBase (topology)Medicinal chemistryCombinatorial chemistryOrganic chemistryComputational chemistryCatalysisMathematical analysisMathematicsCyclopropane Reaction MechanismsOrganic Chemistry Cycloaddition ReactionsOxidative Organic Chemistry Reactions