Here we present a palladium-catalyzed divergent transformative reaction between o-sulfonamido trifluoroacetophenones and 2-en-4-ynyl carbonates. A spectrum of enantioenriched 2,5-dihydrofuran-fused tetrahydroquinolines bearing either a (Z)- or (E)-exocyclic double bond are constructed with moderate to high enantioselectivity from 5-aryl-substituted carbonates by tuning palladium sources, while analogous 2,3-dihydrofuran-fused products are furnished by using 5-alkyl-substituted ones.