Abstract: A route to access 3‐amino‐2,3‐dihydrobenzofurans that utilizes microwave‐assisted organic synthesis to rapidly generate analogues has been developed. The route begins with an acid‐catalyzed, microwave‐assisted aldol condensation to generate chalcone intermediates, followed by a Corey–Bakshi–Shibata reduction and subsequent Sharpless asymmetric epoxidation to access stereoisomeric epoxyalcohols. The final step is a one‐pot, microwave‐assisted, regioselective, acid‐catalyzed epoxide opening with various amines followed by an intramolecular nucleophilic aromatic substitution reaction to generate the 3‐amino‐2,3‐dihydrobenzofurans. This route provides ready access to stereochemically and structurally diverse analogues of these flavonoid scaffolds. Additionally, a pilot library was synthesized, and the biological activity diversity of the chalcones and dihydrobenzofurans was explored in human carcinoma cell lines. [ABSTRACT FROM AUTHOR]