Organocatalyzed diastereo- and enantioselective synthesis of N-N atropisomeric isoindolinones bearing central chirality.

ABSTRACT: Methods for catalytically constructing of N-N axially chiral scaffolds have garnered significant attention since such compounds are widely present in natural products, bioactive molecules, and organic materials. Herein, we report a highly diastereoselective and enantioselective organocatalyzed [4 + 1] annulation method for synthesizing diverse valuable isoindolinones that possessing N-N axial and central chiralities. This methodology uses a chiral phosphoric acid as a bifunctional catalyst to promote a cascade sequence involving two nucleophilic additions, dehydration, and dearomatization processes. Control experiments and DFT calculations revealed a possible mechanism in which the stereoselectivity-determining step is likely to involve the irreversible formation of a hydroxy biaryl interm

SUBMITTER: Li X 

PROVIDER: S-EPMC11830031 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature