Enantioselective formal [3+2]-cycloadditions to access spirooxindoles bearing four contiguous stereocenters through synergistic catalysis
Jun‐An Xiao, Jinlian Li, Xiuliang Cheng, Kai Chen, Hai Peng, Wenqiang Chen, Wei‐Fang Su, Yanmin Huang, Hua Yang
Abstract
An enantioselective ring-opening formal [3+2]-cycloaddition of spirovinylcyclopropyl oxindoles with enals via synergistic catalysis of palladium(0) and a chiral organocatalyst has been developed, affording spirooxindoles bearing four contiguous stereocenters in good yields with excellent enantioselectivities. The generality and utility of the protocol were also demonstrated through scale-up experiments and synthetic transformation of the resulting cycloadduct.
Topics & Concepts
StereocenterEnantioselective synthesisCycloadditionChemistryCatalysisAmine gas treatingRing (chemistry)Combinatorial chemistryStereochemistryOrganic chemistryCyclopropane Reaction MechanismsOxidative Organic Chemistry ReactionsAsymmetric Synthesis and Catalysis