Organocatalytic Kinetic Resolution of Ferroceno[]isoquinolines through Asymmetric Transfer Hydrogenation.

An efficient kinetic resolution of ferroceno-[]-isoquinolines was realized through chiral phosphoric acid-catalyzed asymmetric transfer hydrogenation, affording the planar-chiral ferroceno-[]-isoquinolines and planar-chiral -butyl ferroceno-[]-isoquinoline-4-(5)-carboxylates with a selectivity factor of up to 58. The -Boc group could be easily removed from the reductive product. Moreover, the recovered materials could be transformed into various planar-chiral ferrocene-based bidentate ligands, which were successfully applied in several asymmetric catalytic reactions with excellent yields and enantioselectivities.