investigated the influence of chirality on the lower critical solution temperature (LCST) behavior of water soluble poly(2-alkyl-4-methyl-2-oxazoline)s (alkyl: methyl, ethyl). Introduction of chirality via the alkyl substituents in the main chain of poly(2,4-disubstituted-2-oxazoline)s allows for the formation of secondary structure in aqueous and non-aqueous environments as well as in bulk. In a patent, Schmidt and Bott proposed a possible application of poly(4(S)-4-ethyl-2-phenyl-2-oxazoline) in the separation of enantiomeric mixtures of D,L-2-chloro-4-methyl-phenoxy-propionic acid methylester. As many drugs, including hydrophobic ones, are chiral, it is interesting to study the effect of chirality on POx based drug formulations. While in recent years, significant structure property relationships regarding hydrophobic drug formulations using a large variety of amphiphilic POx have been studied, a drug formulation based on main chain chiral POx has not been studied before. Aiming to improve our understanding of stereoregular polymers as drug carriers in general and to enlarge the toolbox of POx based drug formulations in particular, we have synthesized two series of chiral POx based ABA amphiphilic triblock copolymers. We explored their potential application for drug formulation and their selectivity and affinity for particular drug enantiomers. Specifically, ABA triblock copolymers were synthesized via living cationic ring-opening polymerization (LCROP), comprising pMeOx as hydrophilic blocks A and chiral poly((R)-2-ethyl-4-ethyl-2-oxazoline) (p R EtEtOx), poly((S)-2-ethyl-4-ethyl-2-oxazoline) (p S EtEtOx) and racemic poly((RS)-2-ethyl-4-ethyl-2-oxazoline) (p RS EtEtOx) as well as poly((R)-2-propyl-4-methyl-2oxazoline) (p R PrMeOx), p S PrMeOx and p RS PrMeOx as hydrophobic block B. Their aqueous solubility, optical activity, thermal properties and drug loading with respect to chirality were investigated. The corresponding hydrophobic homopolymers were also synthesized and investigated to help understand the properties of triblock copolymers. Curcumin (CUR) and paclitaxel (PTX) were used as models of common hydrophobic drugs, whereas R-ibuprofen (R-IBU), S-IBU, RS-IBU were used as model compounds for chiral drugs and a racemic drug mixture.