The asymmetric synthesis of tetrahydropyridin-2-ols from enals and enaminones is described. The organocatalytic domino reaction involves a Michael addition–hemiaminalization sequence using the Jørgensen–Hayashi catalyst. Dehydration or oxidation leads to the corresponding 1,4-dihydro-pyridines or 3,4-dihydropyridin-2-ones in a one-pot fashion.