The weak interaction isosurfaces are depicted in Figure . The analysis clearly showed that the phthalimide anion bound to the nickel center through both an N-Ni coordinate bond and a hydrogen bond with the diamine ligand in both transition states. In 3-2_TS, the pinacol moiety of the alkylboron radical formed a hydrogen bond with the chiral diamine ligand, with the methyl group of the alkylboron radical positioned in a manner to avoid steric hindrance from the bromine atom. Conversely, in 3-1_TS, to mitigate the steric hindrance from the chiral ligand, the alkylboron radical adopted a different conformation, resulting in the loss of the hydrogen bond between the pinacol part and chiral diamine ligand. We hypothesized that the hydrogen bond predominantly governed the observed enantioselectivity.