Catalytic Asymmetric 1,4‐Hydrocarbonation of 1,3‐Enynes via Photoredox/Cobalt/Chromium Triple Catalysis
Ju‐Song Yang, Xingyu Wang, Yong-Yao Li, Fu‐Min Zhang, Fu‐Min Zhang, Xiao‐Ming Zhang, Yong‐Qiang Tu
Abstract
A synergistic photoredox/cobalt/chromium triple catalysis system for regioselective, enantioselective, and diastereoselective 1,4-hydrocarbonation of readily available 1,3-enyne precursors was explored, providing a modular synthetic platform for various trisubstituted axially chiral allenes bearing an extra central chirality. The protocol features a broad substrate scope, good functional group tolerance, excellent selectivity, and mild reaction conditions. Furthermore, a possible reaction mechanism is proposed based on numerous control experiments and density functional theory calculations.
Topics & Concepts
CobaltCatalysisEnantioselective synthesisRegioselectivityChemistryAlleneSubstrate (aquarium)Combinatorial chemistrySelectivityDensity functional theoryChirality (physics)Functional groupTriple bondReagentTriple helixChromiumOrganic chemistryStereochemistryComputational chemistrySymmetry breakingPhysicsPolymerQuantum mechanicsGeologyDouble bondNambu–Jona-Lasinio modelChiral symmetry breakingOceanographyCatalytic C–H Functionalization MethodsSynthesis of Indole DerivativesAxial and Atropisomeric Chirality Synthesis