Synthesis of chiral [2,3]-fused indolines through enantioselective dearomatization inverse-electron-demand Diels–Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone
Sihan Zhao, Shaobing Cheng, Hui Liu, Jiayan Zhang, Min Liu, Wei‐Cheng Yuan, Xiaomei Zhang
Abstract
Enantioselective dearomatization inverse-electron-demand Diels-Alder reaction/oxidation of indoles with 2-(2-nitrovinyl)-1,4-benzoquinone was realised using a chiral bisoxazoline/zinc complex as a catalyst. This transformation allowed for the synthesis of enantioenriched six-membered [2,3]-fused indolines (up to 99% yield and 88% ee).
Topics & Concepts
Enantioselective synthesisChemistryBenzoquinoneYield (engineering)Diels–Alder reactionInverseCatalysisOrganic chemistryMaterials scienceMathematicsMetallurgyGeometryOxidative Organic Chemistry ReactionsAlkaloids: synthesis and pharmacologyCatalytic C–H Functionalization Methods