Palladium-Catalyzed Asymmetric Synthesis of Silicon-Stereogenic 5,10-Dihydrophenazasilines via Enantioselective 1,5-Palladium Migration

A palladium-catalyzed asymmetric synthesis of silicon-stereogenic 5,10-dihydrophenazasilines was developed that proceeds via an unprecedented enantioselective 1,5-palladium migration. High enantioselectivity was achieved by employing 4,4'-bis(trimethylsilyl) (R)-Binap as the chiral ligand, and a series of mechanistic investigations were carried out to probe the catalytic cycle of this process.