Umpolung 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines

Significance

The organocatalytic asymmetric inverse-electron-demand 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines is described. Maruoka and co-workers developed new catalysts 1 based on the structure of their original chiral dicarboxylic acid catalysts. Vinylogous aza-enamines, umpolung substrates, were applied to this cycloaddition and the products were obtained in good yields and enantioselectivities. An aza-enamine moiety was converted into the nitrile and the product was obtained in good yield.