Selective approach to N-substituted tertiary 2-pyridones

The regio- and enantioselective amination of readily available vinyl cyclic carbonates with ambivalent 2-hydroxypyridines has been achieved using a Pd(0)/DACH-naphthyl catalyst system. The reaction proceeds under simple conditions, providing access to chiral N-substituted 2-pyridones that bear elusive tertiary carbon centers. A significant drawback previously related to making these products via transition metal-catalyzed allylic substitution procedures is overcome by this catalytic method.

Automated summary

Regio- and enantioselective amination of readily available vinyl cyclic carbonates with ambivalent 2-hydroxypyridines has been achieved using a Pd(0)/DACH-naphthyl catalyst system. The reaction proceeds under simple conditions, providing access to chiral N-substituted 2-pyridones that bear elusive tertiary carbon centers. This catalytic method overcomes a significant drawback previously associated with transition metal-catalyzed allylic substitution procedures.