2025/07/10 by Chao Zhou, Thorsten Bach · 1 voice
Chemistry · Pharmacology, Toxicology and Pharmaceutics · #Asymmetric Hydrogenation and Catalysis #Chemical Reactions and Isotopes #Synthesis and Catalytic Reactions
paper · pdf · doi:10.1021/jacs.5c07524
openalex publication_date 2025/07/10 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/02
Chiral heterocyclic lactams have been kinetically resolved in a photochemical process that involves selective hydrogen abstraction by a chiral benzophenone catalyst. Recognition of one enantiomer is achieved by a two-point hydrogen bonding interaction that directs the reactive carbonyl group of the photocatalyst to the C-H bond at the stereogenic center within the lactam. The generated radical is converted to an oxidized product in a cobaloxime-catalyzed dehydrogenation reaction. The unreactive enantiomer is retained and isolated in enantiomerically enriched form (21 examples, 31-56% yield, 90-99% ee).