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  • Title: Catalytic asymmetric construction of 3,3'-spirooxindoles fused with seven-membered rings by enantioselective tandem reactions.
    Author: Wang Y, Shi F, Yao XX, Sun M, Dong L, Tu SJ.
    Journal: Chemistry; 2014 Nov 10; 20(46):15047-52. PubMed ID: 25255976.
    Abstract:
    The first catalytic asymmetric construction of a spirooxindole scaffold incorporated with a seven-membered benzodiazepine moiety has been established by a three-component (isatin, 1,2-phenylenediamine, cyclohexane-1,3-dione) tandem reaction catalyzed by a chiral phosphoric acid. Structurally complex spirobenzodiazepine oxindoles with one quaternary stereogenic center are obtained in high yield with excellent enantioselectivity (up to 99% yield, enantiomeric ratio>99.5:0.5). This approach takes advantage of organocatalytic asymmetric tandem reactions to efficiently construct the structurally rigid spirobenzodiazepine oxindole architecture with high enantiopurity in a single transformation, which involves a cascade enamine-imine formation/intramolecular Mannich reaction sequence.
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