Described herein is the CuCl2‐catalyzed [4+1] annulation of a variety of propargylamines with N,O‐acetals that function as a C1 unit, leading to the production of polysubstituted pyrrole derivatives. Three important features of the N,O‐acetal during the [4+1] annulation series via 5‐endo‐dig cyclization are described: an enolizable substituent adjacent to the central sp3‐carbon is required, the central sp3‐carbon displays the functions of both an electrophile and a nucleophile, and liberation of the secondary amine smoothly leads to the aromatization.

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