A zinc ProPhenol-catalyzed direct asymmetric aldol reaction between glycine Schiff bases and aldehydes is reported. The design and synthesis of new ProPhenol ligands bearing 2,5-trans-disubstituted pyrrolidines was essential for the success of this process. The transformation operates at room temperature and affords syn beta-hydroxy-alpha-amino esters in high yields with good to excellent levels of diastereo- and enantioselectivity.