The development of novel chiral catalysts is one of the most challenging areas in organic chemistry. This account summarizes our recent studies on chiral bis(imidazoline)-palladium pincer type catalysts (phebim-Pd). The catalysts can be used in the enantioselective reaction of a wide variety of nitrile compounds with imines giving products in high yields with good stereoselectivities. This process offers a simple and efficient route for the synthesis of functionalized β-aminonitriles and their derivatives. We also examine the enantioselective allylation of ketimines derived from isatins using chiral phebim-Pd complexes to afford products in high yields with good enantioselectivities.