Poly(2-oxazoline)s (POx) are a family of polymers of the larger group of polymers classified as pseudopolypeptides. In the past two decades, POx have gained increasing interest for a wide range of applications, especially in the biomedical field, e.g., drug, protein and gene delivery, tissue engineering, regenerative medicine, 3D bioprinting and biofabrication, etc. The 2-oxazoline monomers with different substituents in the 2-position can be tailor-made by relative easy and straightforward synthesis, and numerous monomers have been used in cationic ring-opening polymerization to obtain the corresponding poly(2alkyl/aryl-2-oxazoline)s with narrow molar mass distributions and a wide range of physico-chemical properties. Among them, the hydrophilic POx, poly(2-methyl-2-oxazoline) (pMeOx) and poly(2ethyl-2-oxazoline) (pEtOx) have been studied intensively as they exhibit stealth/protein repellent effects. They are regularly discussed as one of the potential alternatives to PEG. pMeOx and pEtOx have been used widely as hydrophilic polymer component, e.g., in polymer nanoparticles and micelles (in combination with other hydrophobic POx e.g., with 2-butyl, 2-nonyl or 2-isopropyl-2oxazoline ), polymer-peptide conjugates, polymer-protein conjugates, lipopolymers for liposome stabilization, polymer-drug conjugates, as well as antimicrobial polymers. While the toolbox of 2substituted 2-oxazolines and their corresponding polymers has been expanding rapidly, however, work on monomers and polymers with substituents in the 4-and 5-position in the 2-oxazoline monomers is quite limited. The proof-of-principle that such 2,4-disubstituted POx are accessible was provided by Saegusa et al., who synthesized optically active poly(ethylenimine) derivatives by ring-opening polymerization of 4-substituted-2-oxazoline and 4,5-disubstituted-2-oxazoline for the first time. Much later Schubert, Hoogenboom and co-workers reported the synthesis and properties of chiral poly(2-R-4-ethyl-2-oxazoline)s (R = ethyl, butyl, octyl, nonyl, undecyl), and further discussed the self-assembly of chiral amphiphilic block copolymers composed of a hydrophilic block of pEtOx and a hydrophobic block of poly(R-2-butyl-4-ethyl-2-oxazoline) (p R BuEtOx) or racemic p RS BuEtOx. They found that varying the hydrophobic/hydrophilic ratio in the copolymers could control the type of self-assembled structures from spherical and cylindrical micelles to sheets and vesicles. Unfortunately, in this contribution, no direct comparison of chiral and racemic polymers of the same composition was provided. Jordan et al.