A highly efficient stereoselective method for the synthesis of functionalized spirooxindole derivatives with four contiguous stereogenic centers, including two adjacent quaternary stereogenic centers, was realized through an organocatalytic tandem Michael-Michael reaction. By employing a quinidine-derived thiourea organocatalyst, the reaction between (E)-2-cyano-2-(2-oxo-1-tritylindolin-3-ylidene)acetates and (E)-1-alkyl-6-nitro-hex-2-en-1-ones yields the desired spirooxindole products in good yields (up to 90%) and with excellent stereoselectivities (up to 95:5 dr and 98% ee). © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.