Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 5, Pages 2520-2531Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02421
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- Ministry of Science and Technology, Taiwan [109-2113-M-005-018, 110-2113-M-005-024]
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This study reports a new method for a hydrogen-bond-donor-directed enantiodivergent vinylogous aldol-cyclization cascade reaction using thiourea or squaramide cinchona alkaloid catalysts. The results also reveal the kinetic mechanism of the reaction and the enantioselectivity determined by the geometry of the pronucleophile.
In this study, we reported a hydrogen-bond-donor-directed enantiodivergent vinylogous aldol-cyclization cascade reaction of 3-alkylidene oxindoles with isatins and o-quinones. Both enantiomers can be prepared by thiourea or squaramide cinchona alkaloid bifunctional organocatalysts with the same quinine scaffold. Kinetic study data provided the possible reaction mechanism for the vinylogous aldol-cyclization cascade reaction. The DFT calculation data showed the geometry of the generated dienolates from pronucleophiles dominated the observed switch of enantioselectivity.
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