Carbene-Catalyzed Atroposelective Construction of Chiral Diaryl Ethers

Atropoisomeric chemotypes of diaryl ethers-related scaffolds are prevalent in naturally active compounds. Nevertheless, there remains considerable research to be carried out on the catalytic asymmetric synthesis of these axially chiral molecules. In this instance, we disclose an N-heterocyclic carbe...

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Veröffentlicht in:Journal of organic chemistry 2024-06, Vol.89 (11), p.7630-7643
Hauptverfasser: Liu, Yuheng, Yuan, Lutong, Dai, Linlong, Zhu, Qiaohong, Zhong, Guofu, Zeng, Xiaofei
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Sprache:eng
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Zusammenfassung:Atropoisomeric chemotypes of diaryl ethers-related scaffolds are prevalent in naturally active compounds. Nevertheless, there remains considerable research to be carried out on the catalytic asymmetric synthesis of these axially chiral molecules. In this instance, we disclose an N-heterocyclic carbene (NHC)-catalyzed synthesis of axially chiral diaryl ethers via atroposelective esterification of dialdehyde-containing diaryl ethers. NHC desymmetrization produces axially chiral diaryl ether atropisomers with high yields and enantioselectivities in moderate circumstances. Chiral diaryl ether compounds may be precursors for highly functionalized diaryl ethers with bioactivity and chiral ligands for asymmetric catalysis.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c00330