ArticleNature communications2021
Metal-free oxidative cross-coupling enabled practical synthesis of atropisomeric QUINOL and its derivatives.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Control of axial stereochemistry for the enantioselective construction of a QUINAP library.Chemical science · 2026Article
- Photoinduced polarity-mismatched transformations of isoquinolines into naphthalenes.Nature communications · 2026Article
- Asymmetric synthesis of chiral boronic esters featuring nonadjacent axial and flexible, acyclic central chirality.Science advances · 2025Article
- Atroposelective Synthesis of Biaryl N-Oxides via Cu-Catalyzed De Novo Heteroaromatic N-Oxide Ring Formation.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Atroposelective catalysis.Nature reviews. Chemistry · 2024Review
- CspChemical science · 2024Review
- Diversely functionalized isoquinolines and their core-embedded heterocyclic frameworks: a privileged scaffold for medicinal chemistry.RSC medicinal chemistry · 2023Review
- On the Ability of the N-O Bond to Support a Stable Stereogenic Axis: Peptide-Catalyzed AtroposelectiveThe Journal of organic chemistry · 2023Article
- Advances in Atroposelectively De Novo Synthesis of Axially Chiral Heterobiaryl Scaffolds.Molecules (Basel, Switzerland) · 2022Review
- Organocatalytic atroposelective construction of axially chiral N, N- and N, S-1,2-azoles through novel ring formation approach.Nature communications · 2022Article
- Practical synthesis of 3-aryl anthranilsChemical science · 2022Article
- Brønsted acid-enhanced copper-catalyzed atroposelective cycloisomerization to axially chiral arylquinolizones via dearomatization of pyridine.Nature communications · 2022Article
- Organocatalytic atroposelective heterocycloaddition to access axially chiral 2-arylquinolines.Communications chemistry · 2021Article
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Authors and funding
5 authors.
Funding
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Abstract
As an important platform molecule, atropisomeric QUINOL plays a crucial role in the development of chiral ligands and catalysts in asymmetric catalysis. However, efficient approaches towards QUINOL remain scarce, and the resulting high production costs greatly impede the related academic research as well as downstream industrial applications. Here we report a direct oxidative cross-coupling reaction between isoquinolines and 2-naphthols, providing a straightforward and scalable route to acquire the privileged QUINOL scaffolds in a metal-free manner. Moreover, a NHC-catalyzed kinetic resolution of QUINOL N-oxides with high selectivity factor is established to access two types of promising axially chiral Lewis base catalysts in optically pure forms. The utility of this methodology is further illustrated by facile transformations of the products into QUINAP, an iconic ligand in asymmetric catalysis.
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