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Reactivity toward traditionally challenging ester Michael acceptors is achieved through careful catalyst design, enabling the synthesis of enantioenriched pyrrolidines, piperidines, and indoline derivatives in excellent yields (up to 99%) and enantiomeric ratios (up to 97.5:2.5 er) under operationally simple conditions. The broad reaction scope demonstrates excellent tolerance to variation in the sulfonamide group, the Michael acceptor, and substituents on the tether in between. 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