Titanium catalyzed [2σ + 2π] cycloaddition of bicyclo[1.1.0]-butanes with 1,3-dienes for efficient synthesis of stilbene bioisosteres
Yonghong Liu, Zhixian Wu, Jing‐Ran Shan, Huaipu Yan, Er‐Jun Hao, Lei Shi
Abstract
Natural stilbenes have shown significant potential in the prevention and treatment of diseases due to their diverse pharmacological activities. Here we present a mild and effective Ti-catalyzed intermolecular radical-relay [2σ + 2π] cycloaddition of bicyclo[1.1.0]-butanes and 1,3-dienes. This transformation enables the synthesis of bicyclo[2.1.1]hexane (BCH) scaffolds containing aryl vinyl groups with excellent regio- and trans-selectivity and broad functional group tolerance, thus offering rapid access to structurally diverse stilbene bioisosteres.
Topics & Concepts
CycloadditionBicyclic moleculeChemistryCatalysisSelectivityCombinatorial chemistryArylFunctional groupIntermolecular forceStereochemistryMedicinal chemistryOrganic chemistryMoleculeAlkylPolymerRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions