It should also be considered that the H-bonding between the carbonyl lone pair of the incoming substrate and the relatively acidic sites of the catalyst may also contribute to positioning the substrate to collect such changes. The relative importance of this is expected to increase with increasing catalyst electron deficiency and basic character of the substrate carbonyl group. These observations are reconciled with the erosion of enantioinduction observed in substrates bearing ketones, esters, and electron-poor amide substituents, which are less Lewis basic than the amide analogs. Such an effect is connected to the dominant electronic term of the MLR model for the substrates. Previous results on enantioselective non-directed hydroxylation of tertiary C(sp 3 )-H bonds also demonstrated that enantioselectivity is highly sensitive to the position of the carbonyl functionality along the cyclohexane substituent, which affects the establishment of H-bonding interactions. In both scenarios, the increase of the H-bonding capability enforces the interaction of the incoming substrate with the chiral pocket, which likely affects enantiodiscrimination.