Theoretical density functional theory (DFT) calculations were carried out to study bond insertion reactions using a copper(I)-Box-carbenoid as a bond activator. In order to understand the reaction mechanism where N-H and O-H bonds actively participate, the reaction force (RF) and activation strain model (ASM) were used. Results indicate that the first step of the reaction is barrierless for both bond insertions (N-H and O-H), and the second step of the insertion reaction in the phenol (O-H bond) is favored kinetically and thermodynamically with regard to the aniline substrate (N-H bond). The enantioselectivity is driven by the ligand of the catalyst by steric repulsion, favoring the formation of the R isomer. The analysis of the reaction force and ASM exhibited that the higher energy barrier in aniline is mainly due to a higher W-2 contribution together with repulsive interactions, which hinders the insertion process.