Copper-Catalyzed Enantioselective Arylation via Radical-Mediated C-C Bond Cleavage: Synthesis of Chiral ω,ω-Diaryl Alkyl Nitriles

The first example of copper-catalyzed ring-opening, enantioselective arylation of cyclic ketoxime esters to access omega,omega-diaryl alkyl nitriles has been developed in high yield (up to 92% yield) with excellent enantioselectivity (up to 91% ee). Side-arm bis(oxazoline) ligand plays a significant role in this asymmetric catalytic transformation, which provides an efficient route to construct diverse chiral omega,omega-diaryl alkyl nitriles. Synthetic utility has also been demonstrated in the further derivatization of the omega,omega-diaryl alkyl nitrile to the corresponding amide.

Automated summary

The first example of copper-catalyzed ring-opening, enantioselective arylation of cyclic ketoxime esters has been developed with high yield and excellent enantioselectivity. The side-arm bis(oxazoline) ligand plays a significant role in this asymmetric catalytic transformation, providing an efficient route to construct diverse chiral omega,omega-diaryl alkyl nitriles. This synthetic method also demonstrates its utility in further derivatizing the omega,omega-diaryl alkyl nitrile to the corresponding amide.