Palladium-Catalyzed Strain-Enabled [2π + 2σ] Cycloadditions of Vinyl Bicyclo[1.1.0]butanes with Methyleneindolinones
Lan Zheng, Yumin Yang, Zhiping Liu, Wei Wang, Wenjie Liang, Hai-Lian Jiang, Yang Liu, Chenxiang Lin, Wei‐Fang Su, Jun‐An Xiao
Abstract
A palladium-catalyzed [2π + 2σ] cycloaddition of vinyl bicyclo[1.1.0]butanes with methyleneindolinones has been developed. The reaction enables the construction of spirobicyclo[2.1.1]hexanes bearing an all-carbon quaternary center in moderate to good yields with excellent diastereoselectivities. This method features a broad substrate scope with good functional group compatibility. The practical utility of this protocol was further demonstrated by gram-scale synthesis and postsynthetic transformations of desired product.
Topics & Concepts
ChemistryPalladiumBicyclic moleculeCycloadditionCatalysisCompatibility (geochemistry)Combinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistryComposite materialMaterials scienceOxidative Organic Chemistry ReactionsAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization Methods