We herein describe a stereoselective organocatalyzed aza-Michael/Morita-Baylis-Hillman domino reaction between readily accessible acrylamides and α,β-unsaturated carbonyls. This novel, PPh3-promoted atom economic one-pot process features medium to good yields and good stereoselectivity leading to variously substituted piperidin-2-ones bearing an exocyclic olefinic bond, which was shown to be an excellent anchor for further chemical diversification.