The present investigation reports an easy regio-and diastereoselective access to a library of diverse polycyclic pyrrolizidine fused spiro-1,3-indandione/oxindole derivatives through a onepot sequential four-component reactions of 4-oxo-4H-chromene-3-carbaldehyde/2-chloroquinoline-3-carbaldehyde, 1-phenyl-2-(1,1,1-triphenyl-λ 5 -phosphanylidene)ethan-1-one, ninhydrin or isatin, and L-proline in EtOH at room temperature. This protocol features excellent chemical yields, high diastereoselectivity and operational simplicity.