Treatment of 2‐epoxy‐1‐alkynylbenzenes with electron‐rich alkenes and a [AuCl(PR3)]/AgX catalyst in CH2Cl2 led to the formation of 2‐alkenyl‐1‐(2,3‐dihydrofuran‐4‐yl)benzenes. This transformation comprises of a gold‐catalyzed redox reaction to form a gold α‐carbonylcarbenoid initially, which then reacts in situ with an alkene in a [3+2] cycloaddition. A range of alkenes are amenable to this tandem reaction, amongst them α‐substituted styrenes, enol ethers, and 2,3‐dimethylbutadienes. Deuterium‐labeling experiments suggest a stepwise mechanism for the α‐carbonylcarbenoid/alkene [3+2] cycloaddition. The resulting 2,3‐dihydrofuran products allow access to diverse oxacyclic compounds through a stereoselective ene–oxonium reaction initiated by treatment with HOTf (1 mol %; Tf=trifluoromethanesulfonyl). A stepwise pathway is proposed for this reaction. The feasibility for direct transformation of 2‐alkenyl‐1‐alkynylbenzenes into the desired 2,3‐dihydrofuran products through initial m‐chloroperbenzoic acid oxidation, followed by the addition of gold catalyst and alkene, has also been demonstrated.