Atroposelective Brønsted Acid-Catalyzed Photocyclization to Access Chiral N‑Aryl Quinolones with Low Rotational Barriers

Herein, a novel route to atropisomeric N-aryl quinolones with low rotational barriers is demonstrated, leveraging a dual photochemical/organocatalytic approach to the required ring closure in up to 94% yield and up to >99% ee. The use of a continuous flow system allows for impurity suppression an...

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Veröffentlicht in:Organic letters 2023-08, Vol.25 (31), p.5856-5861
Hauptverfasser: Arunachalampillai, Athimoolam, Chandrappa, Prashantha, Cherney, Alan, Crockett, Richard, Doerfler, Jaika, Johnson, Gregory, Kommuri, Venkata Chandrasekhar, Kyad, Ali, McManus, Joshua, Murray, James, Myren, Tessa, Fine Nathel, Noah, Ndukwe, Ikenna, Ortiz, Adrian, Reed, Margaret, Rui, Huan, Silva Elipe, Maria Victoria, Tedrow, Jason, Wells, Shane, Yacoob, Suha, Yamamoto, Kumiko
Format: Artikel
Sprache:eng
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Zusammenfassung:Herein, a novel route to atropisomeric N-aryl quinolones with low rotational barriers is demonstrated, leveraging a dual photochemical/organocatalytic approach to the required ring closure in up to 94% yield and up to >99% ee. The use of a continuous flow system allows for impurity suppression and enables rapid scale-up to a decagram scale.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c02117