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Phosphine-Catalyzed Asymmetric Dearomative [3+2] Annulation Reaction of Benzimidazoles with Cyclopropenones

Shan‐Shan Zhang, Ruixiang Wang, Qing Gu, Shu‐Li You

2024CCS Chemistry21 citationsDOIOpen Access PDF

Abstract

Open AccessCCS ChemistryRESEARCH ARTICLES28 Mar 2024Phosphine-Catalyzed Asymmetric Dearomative [3+2] Annulation Reaction of Benzimidazoles with Cyclopropenones Shan-Shan Zhang, Rui-Xiang Wang, Qing Gu and Shu-Li You Shan-Shan Zhang , Rui-Xiang Wang , Qing Gu and Shu-Li You https://doi.org/10.31635/ccschem.024.202403981 SectionsSupplemental MaterialAboutPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail A phosphine-catalyzed intermolecular asymmetric dearomatization reaction of benzimidazoles with cyclopropenones has been developed. In the presence of 5 mol% of commercially available chiral phosphine catalyst, the dearomative [3+2] annulation reaction proceeds smoothly to afford the corresponding dearomatized heterocycles in excellent yields (up to 98%) and enantioselectivity (up to 99% ee). Meanwhile, this reaction features mild reaction conditions, excellent functional group tolerance, and the compatibility with gram-scale synthesis. Download figure Download PowerPoint Previous articleNext article FiguresReferencesRelatedDetails Issue AssignmentNot Yet AssignedSupporting Information Copyright & Permissions© 2024 Chinese Chemical Society Downloaded 0 times PDF downloadLoading ...

Topics & Concepts

AnnulationPhosphineCatalysisChemistryMedicinal chemistryOrganic chemistryCyclopropane Reaction MechanismsAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods