The diastereo- and enantioselectivetandemcycloisomerization/[4 + 2]-cycloaddition reaction of cyclopropyl tethered allenyl ketones with α,β-unsaturated carbonyl compounds was realized firstly under mild reaction conditions by using bimetallic silver (I)/chiral metal-N,N′-dioxide catalysts, providing a facile and atom-economic route to enantioenriched polysubstituted furopyran derivatives with good