Into the pot: A one-pot highly chemo- and enantioselective catalytic domino oxa-Michael/carbocyclization between α,β-unsaturated aldehydes and propargylic alcohols is presented. This dynamic kinetic transformation requires a combination of transition-metal and amine catalysis to afford functionalized dihydrofurans in good to high yields and up to 99.5:0.5 e.r.