Synthesis of a [2.2]paracyclophane based planar chiral palladacycle by a highly selective kinetic resolution/C-H activation reaction

Kinetic resolution of racemic 4-N,N-dimethylaminomethyl2.2]paracyclophane with 50% sodium tetrachloropalladate and (R)-N-acetylphenylalanine under basic conditions resulted in the formation of a (S(p))-planar chiral palladacycle (35%, >99% ee). Similarly use of 100 mol% sodium tetrachloropalladate resulted in higher levels of conversion and recovery of (S(p))-4-N,N-dimethylaminomethyl2.2]paracyclophane (41%, >97% ee).