Dearomative, aminocatalytic normal-electron-demand aza-Diels-Alder cycloaddition in the synthesis of tetrahydrofuropyridines

In the manuscript the application of dearomative normal-electron-demand aza-Diels-Alder cycloaddition in the synthesis of tetrahydrofuropyridines is described. The developed approach utilizes aminocatalytic activation of 2-alkyl-3-furfurals that proceeds via formation of dearomatized dienamine intermediate. Initially obtained cycloadducts have been subjected to subsequent transformations providing access to tetrahydrofuropyridines or functionalized cinnamates indicating the potential of the developed methodology. The mechanism of the process has been confirmed by DFT calculations.