Diastereodivergent Formal 1,3‐Dipolar Cycloaddition of 5‐alkenyl thiazolones to Access Stereochemically Diverse Pyrrolidinyl Spirooxindoles
Yu He, Yue Liu, Yu Liu, Xin‐Xin Kou, Qing‐Zhu Li, Jiahong Li, Jiahong Li, Hezhong Jiang, Hai‐Jun Leng, Cheng Peng, Jun‐Long Li, Jun‐Long Li
Abstract
Abstract We report here a stereoselective [3+2] cyclization of 5‐alkenyl thiazolones and ketimines that allows the assembly of three diastereoisomers through the combination of stereodivergent organocatalysis and the following diastereoselective transformation of products. A broad spectrum of pyrrolidinyl spirooxindoles featuring stereochemical diversity has been synthesized through organocatalytic formal 1,3‐dipolar cycloadditions with up to 98% yield, >20:1 dr and 99:1 er. magnified image
Topics & Concepts
ChemistryDiastereomerStereoselectivityOrganocatalysisYield (engineering)StereochemistryCycloadditionEnantioselective synthesisTransformation (genetics)Combinatorial chemistryCatalysisOrganic chemistryGeneMetallurgyMaterials scienceBiochemistryAsymmetric Synthesis and CatalysisFluorine in Organic ChemistrySynthesis and Catalytic Reactions