Palladium-Catalyzed Ring Opening of Vinyl Oxetanes Enables Asymmetric Dearomative [6 + 2] Cycloaddition of 3-Nitroindoles to Access Indoline-Fused Oxa-Eight-Membered Rings
Yan Chen, Xinhua Zhang, Zhen‐Hua Wang, Yang Lei, Yong You, Jian‐Qiang Zhao, Ming‐Qiang Zhou, Jihong Lu, Junqing Yin, Wei‐Cheng Yuan
Abstract
, which enables the ring opening of vinyl oxetanes to drive asymmetric dearomatization of 3-nitroindoles for the enantioselective [6 + 2] cycloaddition, leading to the construction of indoline-fused oxa-eight-membered rings in good yields with high to excellent stereoselectivities (up to 96% yield, >95:5 dr, and 98% ee). This work represents the first example of asymmetric dearomatization of electron-deficient nitroindoles triggered by oxa-π-allylpalladium 1,6-dipoles.
Topics & Concepts
Ring (chemistry)ChemistryCycloadditionEnantioselective synthesisCatalysisLigand (biochemistry)Combinatorial chemistryPolymer chemistryStereochemistryWork (physics)Chiral ligandStereoisomerismSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis