Atropselective synthesis of N -aryl pyridones via dynamic kinetic resolution enabled by non-covalent interactions.
Jamie S T SweetRuichen WangPanagiotis ManesiotisPaul DingwallPeter Clarke KnipePublished in: Organic & biomolecular chemistry (2022)
The dynamic kinetic resolution of C-N atropisomeric pyridones was achieved via asymmetric phase-transfer catalysis, exploiting a rotational barrier-lowering hydrogen bond in the starting materials. X-ray and NMR experiments revealed the presence of a barrier-raising ground state CH⋯π interaction in the product, supported by DFT calculations. A co-crystal of the quinidine-derived phase-transfer catalyst and substrate reveals key substrate-catalyst non-covalent interactions.
Keyphrases
- room temperature
- visible light
- density functional theory
- solid state
- high resolution
- ionic liquid
- highly efficient
- reduced graphene oxide
- single molecule
- magnetic resonance
- carbon dioxide
- metal organic framework
- molecular dynamics
- single cell
- electron transfer
- molecular docking
- structural basis
- magnetic resonance imaging
- computed tomography
- dual energy
- monte carlo