A previous report demonstrated that EuDO3A could be used as an NMR shift reagent for imaging extracellular lactate produced by cancer cells using CEST imaging. In this work, a series of heptadentate macrocyclic YbDO3A-trisamide complexes with delta-chiral carbons in the three pendant side-arms were examined as shift reagents for lactate detection. High resolution H-1 NMR spectra and DFT calculations provided evidence for the formation of stereoselective lactate center dot YbDO3A-trisamide complexes each with a different CEST signature. This stereoselectivity allowed discrimination of D- versus L-lactate by both high-resolution NMR and LEST. This work demonstrates that lanthanide-based paramagnetic shift reagents can be designed to detect important metabolites by CEST MRI selectively.