To achieve this, a full re-optimization of our first-generation method was required employing para-cresol as a model nucleophile for non-ortho-substituted phenols. Following an extensive evaluation of new leaving group/ureidopeptide BIMP catalyst combinations, the use of thiazolidinone and B-1 was found to be optimal, utilizing EtOAc as solvent and carrying out the reaction at 0 °C (see Supporting Information for full details). The thiazolidinone mimics the previous nitrophenol leaving group in that it also bears a Lewis basic functionality which can interact with the ureidopeptide through an analogous H-bonding network to obtain the desired products in high enantioselectivity. In addition, due to the higher basicity of the thioazolidinone conjugate base (pKa[DMSO] ≈ 20 vs pKa[DMSO] ≈ 12 for the nitrophenol), 174 higher reaction efficiency was observed, allowing for lower catalyst loadings (Scheme 1, E).