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The first asymmetric decarboxylative [3+2]‐cycloaddition of ethynyl indoloxazolidones with carboxylic acids has been developed under synergistic catalysis of copper and chiral Lewis base. This protocol provides a direct and modular approach to biologically important pyrrolo[1,2‐a]indoles bearing two vicinal stereogenic centers with excellent diastereo‐ and enantioselectivities (up to >20 : 1 dr...