Aromatic rings are common elements in pharmaceutically active compounds; however, their ready oxidation can present a liability with respect to a drug's metabolic stability. Replacing these aromatic rings in pharmaceutical compounds with non-aromatic isosteric motifs can enhance properties such as potency, metabolic stability, solubility, and lipophilicity. Since the binding pockets of most pharmaceutical targets are chiral, the stereochemical configuration of the isosteric replacements are expected to have an impact on the affinity of derived ligands for target receptors. A significant impediment to this approach is the lack of simple, and scalable catalytic enantioselective syntheses of candidate isosteres from readily available precursors. In this work, we present a heretofore unknown palladium-catalyzed reaction that converts hydrocarbon-derived precursors to chiral boron-containing nortricyclanes and we show that that shape of these nortricyclanes makes them plausible isosteres for meta disubstituted aromatic rings. With chiral catalysts, the Pd-catalyzed reaction can be accomplished in an enantioselective fashion and subsequent transformation of the boron group provides access to a broad array of structures. We also show that incorporation of nortricyclanes into pharmaceutical motifs can result in improved biophysical properties along with stereochemistry-dependent activity. We anticipate that these features, coupled with the simple, inexpensive synthesis of the functionalized nortricyclane scaffold will render this platform a useful foundation for assembly of new biologically active agents.