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Herein, an enantioselectively intermolecular direct [3\u2009+\u20092] annulation of aryl amine with 2,3-diketoesters to construct 3-hydroxyindolenines with a chiral tertiary alcohol has been disclosed. The results of control experiments and DFT calculation revealed that \u03c0\u2009\u2212\u2009\u03c0 interaction plays a pivotal role in the enantioselectivity-determining process of [3\u2009+\u20092] annulation. 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