In this paper, we benefit from the expertise of Prof. Luca Muccioli in the modeling of self-assembly monolayers to study the interaction between peptoids and chiral guests. Indeed, peptoids can act as chiral selectors depending on the choice of the side chain. It was demonstrated experimentally that peptoids bearing (S)-N-1-phenylethyl side chains are enantioselective toward binaphthyl derivatives (BINOL) when grafted on silica and used as chiral stationary phase in chromatography columns. In this study, we take advantage of the steered molecular dynamics simulations to get atomistic insights into the factors that rule the enantioselectivity. We identified that these peptoids mainly adopt a right-handed helical conformation, similar to the poly(proline) type I, that better interacts with the (S)-BINOL because of the formation of stronger hydrogen bonds.