Stereoselective Synthesis of CF<sub>3</sub>‐Containing Spirooxindoles via 1,3‐Dipolar Cycloaddition by Dipeptide‐Based Phosphonium Salt Catalysis
Xin Liu, Dongming Lu, Jia‐Hong Wu, Jian‐Ping Tan, Chunhui Jiang, Guowei Gao, Tianli Wang
Abstract
Abstract Reported here is an alternative method for asymmetric synthesis of the CF 3 ‐substituted 3,2′‐pyrrolidinyl spirooxindoles via 1,3‐dipolar cycloaddition by employing dipeptide‐based chiral phosphonium salt as a phase‐transfer catalyst. Under the optimal reaction conditions, a variety of CF 3 ‐substituted 3,2′‐pyrrolidinyl spirooxindole derivatives were readily prepared in high yields as a single diastereomer with high enantiomeric access (>20:1 dr and up to 94% ee). magnified image
Topics & Concepts
ChemistryCycloadditionDiastereomerDipeptideStereoselectivityPhosphonium1,3-Dipolar cycloadditionSalt (chemistry)CatalysisPhosphonium saltEnantiomerEnantioselective synthesisCombinatorial chemistryEnantiomeric excessOrganic chemistryStereochemistryAmino acidBiochemistryFluorine in Organic ChemistryChemical Synthesis and AnalysisCarbohydrate Chemistry and Synthesis