Enantioenriched indole derivatives are of great interest in pharmaceutical science and organic chemistry. Particularly, the indole core is one of the most frequent N-heterocyclic fragment featured in FDA-approved drugs. Therefore, different methods have been designed for the construction of chiral indole scaffolds. The most typical functionalizations of indoles take place at the C3 positions, due to their innate nucleophilicity. In contrast, the development of techniques involving a stereocenter adjacent to the nitrogen, an essential structural motif imbedded in many biologically active molecules (Figure ), 5 remains a great challenge, presumably owing to the attenuated nucleophilicity of the nitrogen atom (Figure ). To this end, a few powerful C-N bond-forming approaches have been developed to access chiral Nalkylindoles (Figure ). However, these transformations often rely on the enantioselective intramolecular addition of prefunctionalized indole substrates, or intermolecular N-alkylation (mostly N-allylation) of indoles with C3-blocking substituents 7 or electron-withdrawing groups. Moreover, indirect methods using indole precursors such as indolines or aryl hydrazines were also developed to obtain high regio-and enantioselectivity. Recently, Buchwald and Vilotijevic demonstrated elegant works using N-modificated strategy to engage N-(benzoyloxy)indoles and N-silyl indoles in C-N bond-forming reactions, respectively. 10 Despite these remarkable advances, a general, modular and selective synthesis of enantioenriched N-alkylindoles is in crucial demand, particularly if the substrates and catalysts are readily available. In sharp contrast to C-N bond-forming process, we questioned whether a relevant C-C bond-forging strategy could allow the coupling of indole-based N-alkylmetal intermediates with electrophiles for the enantioselective synthesis of chiral N-alkylindole architectures (Figure ). The catalytic enantioselective hydrocarbonation of alkenes, enabled by an in-situ generated alkylmetal intermediate through hydrometallation of double bonds, has currently emerged as an attractive protocol for the construction of C-C bonds containing at least a stereogenic sp 3 carbon. 14 However, the alkenes have been classically limited to C-substituted alkenes (G = C, H; Figure ), e.g., styrene derivatives. Catalytic asymmetric hydrocarbonations of heteroatomsubstituted alkenes are comparatively underdeveloped (G = B, N, O, F; Figure ). With respect to readily available N-indolyl-substituted alkenes, their catalytic enantioselective hydrocarbonation is yet to be disclosed to our knowledge (G = N-indolyl, Figure ), but it is highly anticipated given that the desired chiral N-alkylindoles and their derivatives could easily be assembled with this strategy.