The diastereoselective synthesis of novel series of dispiropyrrolidines has been achieved by a one‐pot three‐component [3 + 2] cycloaddition reaction of (E)‐2‐arylideneindanones, glycine ethyl ester, and the cyclic diketones 1H‐indole‐2,3‐dione (isatin) or acenaphthenequinone. Moreover, we disclose an unprecedented epimerization of spiroadducts leading to a new family of dispiropyrrolidines with an unusual relative stereochemistry.
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