Catalytic Asymmetric Synthesis of Tetrahydrofuran Spirooxindoles via a Dinuclear Zinc Catalyst
Yajun Guo, Xin Guo, Dezhi Kong, Huijie Lü, Lantao Liu, Yuan‐Zhao Hua, Min‐Can Wang
Abstract
An asymmetric Michael/hemiketalization and Fridel-Crafts reaction has been reported through a one-pot reaction. A number of structurally novel tetrahydrofuran spirooxindoles are synthesized in the presence of a 10 mol % dinuclear zinc catalyst with diastereomer ratios (dr) of 3:1-13:1 and an enantiomeric excess (ee) of 75-99%. The reaction can be performed on a gram scale without impacting its efficiency. The absolute configuration of products is confirmed by X-ray single crystal structure analysis, and a possible mechanism is proposed.
Topics & Concepts
TetrahydrofuranZincDiastereomerCatalysisChemistryEnantiomeric excessEnantiomerEnantioselective synthesisAbsolute configurationCombinatorial chemistryMedicinal chemistryOrganic chemistrySolventAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry MethodsOxidative Organic Chemistry Reactions