Based on the Phthalimide-Nickel model, we conducted DFT computations on the two proposed pathways: the "TM First" pathway and the "SOA First" pathway. In the "TM First" pathway (Figure elimination to generate products through irreversible exothermic processes. In this pathway, the alkylboron radical addition step dominated the reaction's enantioselectivity; however, the negligible difference between the two transition states was inconsistent with the experimental observations. In the "SOA First" pathway (Figure ), the alkyl radical was added to the Ni I species first, via a low energy barrier (2-3_TS 3.6 kcal/mol), forming the alkyl-Nphth-Ni II intermediate 2-3. Subsequently, the alkylboron radical was added to 2-3 on different faces, resulting in the formation of diastereomeric intermediates 3-1 and 3-2. The following reductive elimination processes were identical to the third step in the "TM First" pathway. In the "SOA First" pathway, the enantio-determining step was also the alkylboron radical addition. The barrier for the S-configuration is 6.1 kcal/mol (3-1_TS), while it was 3.4 kcal/mol for the R-configuration (3-2_TS). The ΔΔG between the two transition states was 2.7 kcal/mol, indicating approximately 98% ee at room temperature, which was consistent with the experimental results.