Asymmetric synthesis of 1-vinyltetrahydroisoquinoline through Pd-catalyzed intramolecular allylic amination

Asymmetric synthesis of 6,7-dimethoxy-1-vinyltetrahydroisoquinolines through Pd-catalyzed intramolecular allylic amination of 3-(amidoethylphenyl)prop-2-enyl carbonates was studied, using a library of fine-tunable monodentate phosphoramidite ligands. Under optimized conditions, excellent enantiopurity (up to 96% ee) and 100% product selectivity were achieved. 1-Vinyltetrahydroquinoline thus obtained is a highly versatile intermediate for the synthesis of various biologically active alkaloids of medicinal interest.