Organocatalytic cascade reactions have been established as a viable and efficient approach to complex molecular architectures,[1] however, examples of the combination of powerful divergent synthesis with an organocatalytic cascade strategy are rare.[2] Herein, we report a powerful divergent organocatalytic cascade reaction that proceeds via a chiral allenamine [3] and involves unprecedented aza-Michael/aldol and aza-Michael/aldol/aromatization ...