Asymmetric metal complex hydrogenation of 1-methyl-3,4-dihydroisoquinoline in the presence of amidophosphite ligand

A number of metal complex precatalysts, solvents, and additives were examined in the asymmetric hydrogenation of 1-methyl-3,4-dihydroisoquinoline in the presence of a chiral amidophosphite ligand. The enantioselectivity of hydrogenation of this substrate increased upon addition of iodine. The best result in the selective hydrogenation was observed when [Ir(COD) 2 ]BARF was used as the precatalyst (COD is the cycloocta-1,5-diene, BARF is the tetrakis[3,5-bis(trifluoromethyl)phenyl]borate).