Transition-Metal-Catalyzed Regiodivergent and Stereoselective Access to Branched and Linear Allylated 4-Pyridones.

A regiodivergent and stereoselective transition-metal-catalyzed addition of 4-pyridones to allenes furnishing N-allylated pyridones is reported. Employing a commercially available chiral rhodium catalyst enabled enantioselective branched-selective allylation. Conversely, an achiral palladium catalyst led to linear-selective N-allylation in high E-selectivities. A wide range of functional groups was tolerated and assorted synthetic transformations of the N-allylated pyridones demonstrated their utility for the syntheses of medicinally relevant heterocyclic scaffolds.