2024/12/30 by Philip Freund, Mike Pauls, Daria Babushkina +3 · 1 voice · 1 citation
Pharmacology, Toxicology and Pharmaceutics · Chemistry · #Fluorine in Organic Chemistry #Synthesis and pharmacology of benzodiazepine derivatives #Chemical Reactions and Mechanisms
paper · pdf · doi:10.1021/jacs.4c16053
openalex publication_date 2024/12/30 · openalex created_date 2024/12/31 · openalex updated_date 2026/06/15
High Resolution Image Download MS PowerPoint Slide By coupling a photochemical and a thermal step, a single chiral catalyst can establish a photostationary state in which the enantiopure form of a chiral compound is favored over its racemate. Following this strategy, 3-substituted 4,7-diaza-1-isoindolones were successfully deracemized (74–98% yield, 86–99% ee ) employing 2.5 mol % of a photocatalyst. Key to the success of the reaction is the fact that a chiral benzophenone recruits selectively one enantiomer of the substrate for a photoinduced hydrogen atom transfer. A combination of computational and experimental studies suggests that the hydrogen atom is shuttled via the oxygen atom of the catalyst to the 4-nitrogen atom of the substrate.