The initiating behavior of the functional tosylates 1-4 and triflates 5 and 6 for the cationic ring-opening polymerization of 2-methyl-1,3-oxazoline was investigated. The emphasis was directed at tosylates and triflates with 2,2-dimethyl-1,3-dioxolane-, 2,3-epoxypropyl-, 2,3-didodecanoyl-glycerol-, and cholest-5-en-moieties that allow the construction of amphiphilic polyoxazoline conjugates. The tosylates were prepared by a simple reaction of the corresponding alcohols with p-toluenesulfonyl chloride, whereas the preparation of the corresponding triflates required low temperature and the use of 2,6-di-tert-butylpyridine as a sterically hindered base. Among the initiators tested, 2,2-dimethyl-(4-trifluoromethanesulfonyloxymethyl)-1,3-dioxolane 6 gave the best results in respect to molecular weight and polydispersity. Starting from the corresponding functional oxazoline polymers obtained with 6 as an initiator, amphiphilic lipid-polyoxazoline conjugates with a diacylglycerol backbone could be prepared.