A rhodium-catalyzed asymmetric 1,4-addition of α/β-(N-indolyl) acrylates to access highly enantioenriched chiral N-alkylindoles promoted by chiral diene or sulfur-olefin ligands under mild reaction conditions has been developed, which provides an efficient and practical approach for constructing carbon stereocenters adjacent to the indole nitrogen. The reaction can be applied to various N-indolyl-substituted α,β-unstaturated esters and arylboron reagents, providing access to a wide range of α- and β-(N-indolyl) propionate derivatives in high yields with excellent enantioselectivities (≤99% ee).