Chiral Bicyclic Imidazole-Catalyzed Acylative Dynamic Kinetic Resolution for the Synthesis of Chiral Phthalidyl Esters was written by Zhou, Muxing;Gridneva, Tatiana;Zhang, Zhenfeng;He, Ende;Liu, Yangang;Zhang, Wanbin. And the article was included in Angewandte Chemie, International Edition in 2021.Electric Literature of C9H8O3 This article mentions the following:
Utilizing a chiral bicyclic imidazole organocatalyst, I, and adopting a continuous injection process, an alternative route has been developed for the efficient synthesis of chiral phthalidyl ester prodrugs via dynamic kinetic resolution of 3-hydroxyphthalides through enantioselective acylation (up to 99% ee). The computational studies suggest a general base catalytic mechanism differing from the widely accepted nucleophilic catalytic mechanism. The structure anal. of the key transition states shows that the CH-π interaction, and not the previously considered cation/π-π interactions between the catalyst and substrate, is the dominant factor giving rise to the observed stereocontrol. In the experiment, the researchers used many compounds, for example, 5-Methoxyisobenzofuran-1(3H)-one (cas: 4741-62-2Electric Literature of C9H8O3).
5-Methoxyisobenzofuran-1(3H)-one (cas: 4741-62-2) belongs to benzofurans derivatives. Benzofuran derivatives have shown many biological activities, including antifungal and antimicrobial properties, and acting as antagonists of H3 receptors and angiotensin II. They are also prone to polymerisation in the presence of concentrated mineral acids and Lewis acids.Electric Literature of C9H8O3
Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem