ArticleJACS Au2024
Deracemization of Atropisomeric Biaryls Enabled by Copper Catalysis.
Article in JACS Au, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Control of axial stereochemistry for the enantioselective construction of a QUINAP library.Chemical science · 2026Article
- Chiral Brønsted acid-catalyzed kinetic resolution of radical additions.Nature communications · 2026Article
- Cooperative Copper/Lipase Catalysis for the Chemoenzymatic Dynamic Kinetic Resolution (DKR) of Bis(hetero)arenols.JACS Au · 2025Article
- Article
- Synthetic, Computational, and Experimental Studies of a Class 3 Atropisomeric α-Naphthyl Tropone.The Journal of organic chemistry · 2025Article
- Azapeptide Atropisomers From Late-StageThe Journal of organic chemistry · 2025Article
- Overcoming the Limitations of Transition-Metal Catalysis in the Chemoenzymatic Dynamic Kinetic Resolution (DKR) of Atropisomeric Bisnaphthols.ACS central science · 2024Article
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Authors and funding
3 authors.
Funding
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Abstract
Atropisomeric biaryls have found crucial applications in versatile chiral catalysts as well as in ligands for transition metals. Herein, we have developed an efficient crystallization-induced deracemization (CID) method to access chiral biaryls from their racemates with a chiral ammonium salt under copper catalysis including BINOL, NOBIN, and BINAM derivatives. After being significantly accelerated by its bidentate diamine ligand, the copper catalyst exhibits high efficiency and selectivity in racemizing biaryl skeletons, and the cocrystal complex would be enantioselectively formed together with chiral ammonium salt, which on acid-quenching would directly deliver chiral biaryl without further chromatographic purification. This CID process is easily scalable, and the chiral ammonium salt was nicely recoverable. Ligand effect studies showed that bulky alkyl substitution was an indispensable element to ensure efficient racemization, which probably proceeds via a radical-cation intermediate and further allows axial rotation by forming a delocalized radical.
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Registered trials
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