Allylic fluorides are ubiquitous scaffolds in the architecture of pharmaceuticals, agrochemicals, materials chemistry, and positron emission tomography (PET) imaging. Recently, methodologies have focused on the utilization of transition-metal catalysis to forge allylic carbon-fluoride bonds. My dissertation describes the development of a new procedure for the synthesis of enantiopure allylic fluorides utilizing iridium catalysis. Additionally, this method was derivatized for the production of allylic [18F]fluorides as potential radiotracers for qualitative and quantitative assessment of disease state.