In　the　presence　of　a　Cinchona　alkaloid-based　squaramide　organocatalyst,　the　[3+2]　cycloaddition　of　isatin-derived　azomethine　ylides　with　maleimides　proceeded　readily,　thus　delivering　the　desired　pyrrolidine-fused　spirooxindoles　in　61-89%　yields　with　＞20:1　dr　and　12　to　＞99%　ee.　The　absolute　configuration　of　5-chloro-1,5-dimethyl-3-phenyl-3,3a-dihydro-2H-spiro[indoline-3,1-pyrrolo[3,4-c]pyrrole]-2,4,6(5H,6aH)-trione　was　unambiguously　determined　by　means　of　X-ray　single　crystal　structure　analysis.　The　reaction　mechanism　was　hypothesized　to　account　for　the　enantioselective　formation　of　5-chloro-1,5-dimethyl-3-phenyl-3,3a-dihydro-2H-spiro[indoline-3,1-pyrrolo[3,4-c]pyrrole]-2,4,6(5H,6aH)-trione.