Diazabicycloalkanes and pyridazines are highly valued nitrogen-containing heterocycles, esteemed for their extensive range of biological activities. Symmetric diazabicycloalkanes, characterized by a unique structure comprising a condensed bicyclic ring system bridged by two nitrogen atoms, are particularly intriguing. Despite established methods for synthesizing chiral pyridazines, the one-step synthesis of condensed diazabicycloalkanes remains a considerable challenge. Current methodologies predominantly employ multi-step synthesis which not only suffers from low atom economy but also imposes limitations on the final heterocyclic structure. Our novel approach accomplishes the one-step synthesis of chiral diazabicycloalkanes by introducing the annulated ring system within a single reaction step. This is achievable through the use of an organocatalytic aza-Michael/aldol process involving the enal substrate class. By employing simple diphenylethylendiamine frameworks as dual activation organocatalysts, we effectively engage both substrate and reagent, resulting in moderate to high yields and high enantioselectivities (ranging from 80-98%). Remarkably, our method demonstrates excellent functional group tolerance across various enals and allows for in situ modification of the product aldehyde motif without compromising enantioselectivity. Furthermore, through adjustment of the quantity of acid cocatalyst, we showcase the tunability of enantioselectivity and yield, offering multiple optimization pathways for this synthetic methodology.1 (1) Scharinger, F.; Weil, M.; Schnürch, M.; Bica‐Schröder, K. Synthesis of Chiral Diazabicycloalkanes via Organocatalytic Aza‐Michael/Aldol Reaction. Adv. Synth. Catal. 2024, 366 (1), 49–55. https://doi.org/10.1002/adsc.202301125.