Kinetic Resolution of Benzylamines via Palladium(II)-Catalyzed C–H Cross-Coupling

A Pd­(II)-catalyzed
enantioselective C–H cross-coupling of
benzylamines via kinetic resolution has been achieved using chiral
mono-N-protected α-amino-O-methylhydroxamic acid (MPAHA) ligands. Both chiral benzylamines
and ortho-arylated benzylamines are obtained in high
enantiomeric purity. The use of a readily removable nosyl (Ns) protected
amino group as the directing group is a crucial practical advantage.
Moreover, the ortho-arylated benzylamine products
could be further transformed into chiral 6-substituted 5,6-dihydro­phenanthridines
as important structural motifs in natural products and bioactive molecules.