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Herein, we described the event of stereodivergent assembly of tetrahydro-γ-carbolines by means of a synergistic Cu/Ir catalyst program to realize a stereodivergent allylation of aldimine esters and indolyl allylic carbonates followed by a spontaneous intramolecular iso-Pictet-Spengler cyclization. The stereochemical consequence of the cascade proc