Enantioselective Copper-Catalyzed Radical Cyanation of Propargylic C-H Bonds: Easy Access to Chiral Allenyl Nitriles

The first enantioselective copper-catalyzed cyanation of propargylic C-H bonds via radical relay was established using novel Box(OTMS) ligands, providing an efficient and straightforward tool for the construction of structurally diverse chiral allenyl nitriles in good yields with excellent enantioselectivities. This reaction features high functional group tolerance and mild conditions. In addition, the chiral allene products can be readily converted to other chiral compounds via axis-to-center chirality transfer.

Automated summary

The first enantioselective copper-catalyzed cyanation of propargylic C-H bonds via radical relay has been established using novel Box(OTMS) ligands, providing an efficient tool for constructing structurally diverse chiral allenyl nitriles with high yields and excellent enantioselectivities. The reaction features high functional group tolerance and mild conditions, and the chiral allene products can be easily converted to other chiral compounds via axis-to-center chirality transfer.