Atroposelective Brønsted Acid-Catalyzed Photocyclization to Access Chiral <i>N</i>-Aryl Quinolones with Low Rotational Barriers
A. Arunachalampillai, Prashantha Chandrappa, Alan H. Cherney, Richard Crockett, Jaika Doerfler, Gregory D. Johnson, Venkata Chandrasekhar Kommuri, Ali Kyad, Joshua McManus, James I. Murray, Tessa Myren, Noah F. Fine Nathel, Ikenna E. Ndukwe, Adrian Ortiz, Margaret A. Reed, Huan Rui, Maria Victoria Silva Elipe, Jason S. Tedrow, Shane Wells, Suha Yacoob, Kumiko Yamamoto
Abstract
-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.
Topics & Concepts
ChemistryAtropisomerYield (engineering)CatalysisArylBrønsted–Lowry acid–base theoryRing (chemistry)Combinatorial chemistryScale (ratio)Medicinal chemistryStereochemistryOrganic chemistryPhysicsThermodynamicsQuantum mechanicsAlkylAxial and Atropisomeric Chirality SynthesisBiological and pharmacological studies of plantsPlant and Fungal Species Descriptions