The stereoselective construction of fluorinated architectures is of great importance in medicinal chemistry, as fluorination can profoundly improve the pharmacokinetic profiles of bioactive molecules. Nonetheless, the enantioselective synthesis of fluorine-containing natural product derivatives continues to pose a significant challenge. In this work, we describe a highly exo- and enantioselective Diels–Alder reaction enabled by a novel diboronate complex generated from bispyrrolidine diboronate (BPDB) in combination with Lewis and Brønsted acids. This strategy provides efficient access to structurally diverse fluorinated abietane diterpenes with high stereocontrol.