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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.
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Yuheng Liu
Hangzhou Normal University
Lutong Yuan
Hangzhou Normal University
Linlong Dai
Shanghai Jiao Tong University
The Journal of Organic Chemistry
Hangzhou Normal University
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Liu et al. (Mon,) studied this question.
synapsesocial.com/papers/68e6a4f8b6db643587628296 — DOI: https://doi.org/10.1021/acs.joc.4c00330