Our group has performed theoretical studies into spiro-phosphoric acid (SPA) catalyzed decarboxylative protonation of aminomalonic acids. The calculation unveiled a step-wise mechanism within our system, involving separated rate-determining step and enantioselective step, which are self-decarboxylation and SPA catalyzed protonation respectively. To decipher the origin of enantioselectivity, we used Independent Gradient Model based on Hirshfeld Partition (IGMH) analysis, providing a qualitative perspective on weak interactions between aminomalonic acid and SPA. Moreover, energy decomposition analysis (EDA) was introduced to break down interaction between fragments along reaction pathway, giving a complement to IGMH study, showing the origin of enantioselectivity in a quantitative level. Anchoring group in aminomalonic facilitates the construction of a coordinated network of noncovalent interactions (NCIs) with SPA. These interactions, primarily dispersion forces, staging an enantioselective decarboxylative protonation to give α-amino acids.