Enantioselective Copper-Catalyzed Radical Cyanation of Propargylic C–H Bonds: Easy Access to Chiral Allenyl Nitriles
Ronghua Lu, Tilong Yang, Xin Chen, Wenzheng Fan, Pinhong Chen, Zhenyang Lin, Guosheng Liu
Abstract
The first enantioselective copper-catalyzed cyanation of propargylic C–H bonds via radical relay was established using novel BoxOTMS 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.
Topics & Concepts
CyanationChemistryEnantioselective synthesisAlleneCatalysisCombinatorial chemistryAxial chiralityChirality (physics)Functional groupCopperStereochemistryMedicinal chemistryOrganic chemistryChiral symmetry breakingPhysicsPolymerQuarkNambu–Jona-Lasinio modelQuantum mechanicsCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques