The first example of organocatalytic enantioselective C–H insertion reactions of indoles and sulfoxonium ylides is reported. Under the influence of phosphoric acid catalysis, levels of enantiocontrol in the range of 20–93% ee and moderate yields (up to 50%) were achieved for 29 examples in formal C–H insertion reactions of free indoles and α-carbonyl sulfoxonium ylides. No nitrogen protection on the indole is necessary.