The venerable Mannich reaction using p-anisidine, aldehyde, and a nucleophile affords a linear α-secondary amine motif. Herein, we report that a slight yet rational modification of the reaction inputs diverts this three-component reaction, rendering a cyclic α-tertiary amine. 2,2-Disubstituted indolin-3-ones equipped with diversified substitution patterns on their de novel generated quaternary carbon centers are readily accessible through this unprecedented transformation. Mechanistically, a domino sequence involving a kinetically favored intramolecular 1,2-aryl migration and copper-catalyzed aerobic oxidation of an activated α-aminoalkyl site is suggested to account for the reaction outcome.

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