5-Substituted-furan-2(3H)-ones in [8+2]-Cycloaddition with 8,8-Dicyanoheptafulvene

This study demonstrates the use of organocatalytic Bronstedbase activation of 5-substituted-furan-2(3H)-ones to generate 2 pi-compo-nents for the diastereoselective [8 + 2]-cycloaddition involving 8,8-dicyanoheptafulvene as an 8 pi-component. The use of dienolates in ahigher-order cycloaddition reaction leads to the formation of biologicallyrelevant polycyclic products bearing a gamma-butyrolactone structural motif, thus broadening the synthetic potential of Bronsted base activated higher-order cycloadditions

Automated summary

This study demonstrates the use of organocatalytic Brønsted base activation to generate 2π-components for the diastereoselective [8 + 2]-cycloaddition reaction involving 8,8-dicyanoheptafulvene. The use of dienolates leads to the formation of biologically relevant polycyclic products bearing a γ-butyrolactone structural motif, thus expanding the synthetic potential of Brønsted base activated higher-order cycloadditions.