This article describes a new method for asymmetric intermolecular aminoarylation of alkenes using enantioenriched arylsulfinylamides as multifunctional reagents. The reaction proceeds under mild photoredox conditions, involving the addition of the nitrogen atom of the arylsulfinylamide to the double bond, followed by a 1,4-translocation of the aromatic ring. This process forms the corresponding aminoarylation adducts in enantiomerically enriched form. The sulfinyl group acts as a traceless chiral auxiliary, being eliminated in situ during the reaction. The method allows for the efficient synthesis of optically pure β,β-diarylethylamines, aryl-α,β-ethylenediamines, and α-aryl-β-aminoalcohols with excellent levels of regio-, relative, and absolute stereocontrol. These compounds are important motifs in pharmaceuticals, bioactive natural products, and transition metal ligands. The reaction is compatible with a wide variety of N-atom donors and olefinic partners, and is tolerant of various functional groups. The mechanism involves the formation of a radical cation for electron-rich olefins or an amidyl radical for vinylamide acceptors. The reaction is stereoselective, with the stereochemistry of the product determined by the configuration of the chiral sulfoxide tether. The method offers a powerful, atom-economic alternative to access these important chemical motifs in a single operation, with broad functional-group tolerance and excellent enantioselectivity. The study highlights the synthetic utility of this methodology in the assembly of relevant blueprints in pharmaceuticals, bioactive natural products, and transition-metal catalysis.This article describes a new method for asymmetric intermolecular aminoarylation of alkenes using enantioenriched arylsulfinylamides as multifunctional reagents. The reaction proceeds under mild photoredox conditions, involving the addition of the nitrogen atom of the arylsulfinylamide to the double bond, followed by a 1,4-translocation of the aromatic ring. This process forms the corresponding aminoarylation adducts in enantiomerically enriched form. The sulfinyl group acts as a traceless chiral auxiliary, being eliminated in situ during the reaction. The method allows for the efficient synthesis of optically pure β,β-diarylethylamines, aryl-α,β-ethylenediamines, and α-aryl-β-aminoalcohols with excellent levels of regio-, relative, and absolute stereocontrol. These compounds are important motifs in pharmaceuticals, bioactive natural products, and transition metal ligands. The reaction is compatible with a wide variety of N-atom donors and olefinic partners, and is tolerant of various functional groups. The mechanism involves the formation of a radical cation for electron-rich olefins or an amidyl radical for vinylamide acceptors. The reaction is stereoselective, with the stereochemistry of the product determined by the configuration of the chiral sulfoxide tether. The method offers a powerful, atom-economic alternative to access these important chemical motifs in a single operation, with broad functional-group tolerance and excellent enantioselectivity. The study highlights the synthetic utility of this methodology in the assembly of relevant blueprints in pharmaceuticals, bioactive natural products, and transition-metal catalysis.