Through the initial screening and further rational design of chiral cyclopentadienyl ligands, a chiral rhodium-catalyzed enantioselective 1,2-carboamidation of aromatic tethered alkenes was developed, enabling the asymmetric preparation of various chiral 2,3-dihydro-3-benzofuranmethanamides with an enantioenriched all-carbon quaternary center at the β position of amide. This robust transformation has a broad functional group tolerance, excellent enantioselectivities (up to 98.5:1.5 er), and a mild reaction conditions, releasing CO2 as the single byproduct.