Alkenes are inexpensive, widely available chemical feedstocks that can be sourced from petroleum or renewable resources. The goal of research in the Engle lab is to develop novel catalytic alkene functionalization reactions that introduce new functional groups at each of the alkenyl carbon atoms in a programmable fashion. In this way, simple planar starting materials can be directly converted into densely functionalized, stereochemically defined products, which can then serve as building blocks for structurally complex target molecules that are of academic and industrial importance, including many widely used pharmaceutical agents. To this end, the Engle lab has developed strategies involving directing auxiliaries, native directing groups, and transient directing groups, as well as complementary non-directed approaches that are compatible with a variety of metals, redox manifolds, and coupling partners. Detailed mechanistic studies have shed light on the interplay between the substrate, metal, and ancillary ligands in dictating reaction outcomes, informing new catalyst designs through an iterative feedback loop.