Abstract An organocatalyzed one-pot Michael addition-Pictet–Spengler sequence of β- ketoamides and α, β-unsaturated aldehydes was developed, which provided access to highly substituted indolo [2, 3-α] quinolizidines and benzo [α] quinolizidines in moderate to good yields and good to excellent enantioselectivities. For aromatic α, β-unsaturated aldehydes 1a–j products 10a–r containing a stable enol configuration were obtained.