The ChelpGR Boltz value calculated on the N of amide S1 (-0.846) is comparatively different from that calculated on the O of ester analog S2 (-0.471) and captures the significant variation in enantioinduction determined by the two groups. Analogously, the erosion in ee observed when decreasing the Lewis basic character of the amide nitrogen (direct comparison between S7 (-0.833) and S14 (-0.720)), or by appending an electrophilic carbon atom (substrates S5 (0.660) and S6 (0.536)) is described by the model.