Bringing together our model reaction, and selective recognition of amine (S)-1, we evaluate the TIPS-β-CD as an SPG in the reaction between racemic (R/S)-1 and benzaldehyde (2a) in presence of Amberlyst 15 at different temperatures (see Fig 3, and SI, Table ). In our initial experiment, the reaction was conducted with 2 equivalents of (R/S)-1 at room temperature (relative to aldehyde 2a), and we obtained 90% conversion observed with 3.6% enantiomeric excess (ee). Progressively lowering temperature lead to progressively increasing chiral selectivity in product 4a, up to 90% ee, with only a minimal drop in conversion (ca. 80%). Decreasing the amount of limiting reagent added (aldehyde) to 0.2 eq at the lowest temperature led to only a modest increase in selectivity (ee = 91.4%), and the use of a different aldehyde (2b, 4-Nitrobenzaldehyde) provided similarly high yield and selectivity profiles to 2a (see SI, Section 6).