Enantioselective Synthesis of Functionalized Chiral Diarylalkanes via Chiral Phenanthroline-Cu-Catalyzed Alkynylation and Amination of Six-Membered Cyclic Diaryliodonium Salts

Highly functionalized chiral diarylalkanes containing C(sp 2 )–I bonds and bearing either various alkyne groups or N -alkoxy sulfonamide groups have been synthesized in up to 99% yield with up to a 98:2 enantiomeric ratio (er) through chiral phenanthroline ligand-enabled Cu-catalyzed asymmetric alkynylation and amination of six-membered cyclic diaryliodonium salts. Furthermore, the amination products can be readily converted to biologically relevant chiral 3,4-dihydroquinolin-2(1 H )-ones in one step, with nearly complete retention of enantiopurity.