Facile access to enantioenriched isoindolines bearing a quaternary stereogenic center and a tertiary stereogenic center was successfully developed via highly efficient Cu(I)/(S,Rp)-PPFOMe-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylide with quinone derivatives followed by silica-gel-promoted oxidation [corrected] in a one-pot reaction protocol. The present catalytic system exhibited high diastereoselectivity, excellent enantioselectivity, and a broad substrate scope under mild conditions.