Asymmetric Intramolecular O -Hydroximation of Alkynes

Open AccessCCS ChemistryRESEARCH ARTICLES27 May 2024Asymmetric Intramolecular O-Hydroximation of Alkynes Chao Ma, Liang Chen and Zhi-Tao He Chao Ma , Liang Chen and Zhi-Tao He https://doi.org/10.31635/ccschem.024.202404296 SectionsSupplemental MaterialAboutPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail Asymmetric hydrofunctionalization of alkynes has developed into a powerful method to construct stereogenic centers. However, the corresponding hydroximation reaction is unexplored. Here we report the development of asymmetric hydroximation reaction of alkynes via rhodium catalyst and α-hydroxyl carboxylic acid as a synergistic Bronsted acid catalyst. A series of privileged aryl isoxazoline skeletons are achieved in high yields and excellent enantioselectivities through exclusively O-addition instead of typical N-addition. This protocol represents a general synthetic model and is applied to the enantioselective concise synthesis of seven biologically active molecules, most of which are prepared through a catalytic asymmetric route for the first time. Mechanistic studies suggest the C-O bond formation as rate-determining step through an inner-sphere substitution process. Download figure Download PowerPoint Previous articleNext article FiguresReferencesRelatedDetails Issue AssignmentNot Yet AssignedSupporting Information Copyright & Permissions© 2024 Chinese Chemical Society Downloaded 0 times PDF downloadLoading ...