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The cascade cyclization reactions of 1,5‐bisallenes grant access to a great variety of products by precisely tuning the catalyst system and/or the reagents involved. Herein, we present our findings that 1,5‐bisallenes react with two molecules of dimethyl acetylenedicarboxylate to afford, in a completely diastereoselective manner, cis‐3,4‐arylvinyl pyrrolidines and cyclopentanes. DFT calculations have...