Enantioselective organocatalyzed cascade reactions to highly functionalized quinolizidines

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.