Atroposelective synthesis of N–N axially chiral pyrrolyl(aza)-quinolinone by de novo ring formation

Abstract

A chiral phosphoric acid-catalyzed Paal–Knorr reaction was achieved for constructing axially chiral pyrrolyl(aza)quinolinones with ‘6–5’-membered rings as a new family member of N–N atropisomers.

Synthesis of N–N Axially Chiral Pyrrolyl-oxoisoindolin via Isothiourea-Catalyzed Acylative Dynamic Kinetic Resolution

“…Despite its great potential, it was not until 2021 that the first reported atroposelective synthesis of N–N axially chiral . Subsequently, Liu, Shi, Sparr, Hong, Yang, Teng, Niu, Zhao, Wang, and Li synthesized atropisomeric N–N bispyrroles, indole pyrroles, bisindoles, and nonbiaryl via de novo construction using palladium-catalysis, NHC catalysis and chiral phosphoric acid catalysis (Scheme b). Lu, Bencivenni, Chi and our group also realized the construction of N–N atropisomers via selective N–H functionalization such as allylation, alkylation, and acylation.…”