With the chiral diamine in hands, we have evaluated the Pd-catalyzed hydroarylation reaction of ketimine 15 we studied earlier with the corresponding enantiomer 1. As expected, chiral sulfonamide was obtained in 98% yield with 91% ee which has the opposite configuration to the ones we have previously reported. However, the corresponding diamine 14 only provided the desired product (S)-17 in 6% ee. In this research, we have successfully prepared chiral diamines (-)-1 and (+)-1 selectively under practical procedures with useful yields (Scheme 4). The access of this chiral ligand with both enantiomers have paved a new path for the future development of chiral diamine ligands with bispidine/quinolizidine like skeleton. The further reaction optimization is currently ongoing.