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We report herein an enantioselective [3+3] annulation of indoline‐2‐thiones with yne–enones by chiral dinuclear zinc catalysts via a Brønsted base and Lewis acid cooperative activation model. This transformation proceeded through sequential conjugate addition, allenyl ketone formation and intramolecular sulfa‐Michael 6‐endo‐trig cyclization. A range of enantioenriched tetrahydrothiopyrano[2,3‐b]indole...