Copper-catalyzed coupling of imines, dienylstannanes and acryloyl chlorides followed by a Diels-Alder reaction allowed for a rapid construction of substituted hexahydro-1H-isoindolones. The methodology demonstrates a new concept in utilizing a-substituted amides as templates for diversity oriented synthesis, and provides a new uniquely useful tool for a future construction of isoindolone combinatorial libraries. The strategy provides five points of diversity, four of which arise from the selection of building blocks. Furthermore, Pd-catalyzed C-C bond forming reactions open up multiple avenues for a final structural diversification.