Enantioselective Dearomative Cyclization Enabled by Asymmetric Cooperative Gold Catalysis.
Ke ZhaoPhilip KohnkeZiguang YangXinpeng ChengShu-Li YouLiming ZhangPublished in: Angewandte Chemie (International ed. in English) (2022)
A gold(I)-catalyzed enantioselective dearomatization is achieved via metal-chiral ligand cooperation. A new and divergent synthesis of chiral bifunctional binaphthyl-2-ylphosphines is developed to allow rapid access to these ligands, which in turn facilitate the application of this chemistry to a broad substrate scope including 1-naphthols, 2-naphthols, and phenols. Enantiomeric excesses up to 98 % are achieved via selective acceleration of one enantiomer formation enabled by hydrogen bonding between substrate and ligand remote basic group. DFT calculations lend support to the cooperative catalysis and substantiate the reaction stereochemical outcomes.
Keyphrases
- capillary electrophoresis
- density functional theory
- ionic liquid
- mass spectrometry
- molecular dynamics
- silver nanoparticles
- room temperature
- fluorescent probe
- molecular dynamics simulations
- sensitive detection
- amino acid
- structural basis
- living cells
- drug discovery
- solid state
- weight loss
- monte carlo
- glycemic control
- single molecule