Atroposelective Brønsted Acid-Catalyzed Photocyclization to Access Chiral N -Aryl Quinolones with Low Rotational Barriers.
Athimoolam ArunachalampillaiPrashantha ChandrappaAlan CherneyRichard CrockettJaika DoerflerGregory JohnsonVenkata Chandrasekhar KommuriAli KyadJoshua McManusJames MurrayTessa MyrenNoah Fine NathelIkenna NdukweAdrian OrtizMargaret ReedHuan RuiMaria Victoria Silva ElipeJason TedrowShane WellsSuha YacoobKumiko YamamotoPublished in: Organic letters (2023)
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.