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Chiral indoline‐2‐carboxylic acid has been identified to enable a highly enantioselective Catellani‐type annulation of (hetero)aryl, alkenyl triflate and conjugated vinyl iodides with 4‐(bromomethyl)cyclohexanone, directly assembling a diverse range of chiral all‐carbon bridged ring systems. Control experiments and DFT calculations suggest that the coordinating orientation of the chiral amino acid to the arylpalladium(II) center allows for high levels of stereochemical control. [ABSTRACT FROM AUTHOR]