A rhodium-catalyzed C-H functionalization-based intermolecular allylation of indoles with trisubstituted allenes has been developed. This synthetic process proceeds with an excellent regioselectivity, Z-selectivity, high efficiency of chirality transfer, and a wide tolerance of reactive functional groups under mild conditions. Late-stage modification on a series of complex bioactive or drug molecules and various synthetic transformations has been demonstrated. A reaction mechanism has been proposed on the basis of mechanistic experiments and SAESI-MS studies.