Counterion-Mediated Enantioconvergent Synthesis of Axially Chiral Medium Rings.

ABSTRACT: There are few enantioconvergent reactions in which racemic substrates bearing multiple stereochemical features are converted into products with high levels of diastereo- and enantiocontrol. Here, we disclose a process for the highly enantio- and diastereoselective syntheses of medium ring lactams via an intramolecular counterion-directed C-alkylation reaction. The treatment of racemic biaryl anilides that exist as a complex mixture of enantiomers and diastereoisomeric conformers by virtue of multiple axes of restricted rotation with a quinidine-derived ammonium salt under basic conditions affords medium ring lactams bearing elements of both axial and point chirality via an enolate-driven configurational relaxation process. Thermal equilibration of the syn- and anti-pro

SUBMITTER: Du JY 

PROVIDER: S-EPMC9394463 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature