Asymmetric Synthesis of α-Quaternary γ-Lactams through Palladium-Catalyzed Asymmetric Allylic Alkylation

Article abstract of DOI:10.1021/acs.orglett.8b03613

The synthesis of chiral unsaturated γ-lactams is reported featuring a highly enantioselective palladium-catalyzed asymmetric allylic alkylation of α, γ-disubstituted 2-silyloxypyrroles. This method allows a straightforward access to optically active γ-lactams bearing an α-quaternary stereogenic center in high yields (up to 93%), high regioselectivities (up to >20:1), and excellent enantioselectivities (up to 95% ee). To further demonstrate the synthetic utility of the method, the resulting allylated products were converted to various versatile chiral building blocks, such as pyrrolidines and pyrrolidinones.