Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/162373
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dc.contributor.authorLi, Shuangqingen_US
dc.contributor.authorWang, Shuangshuangen_US
dc.contributor.authorLi, Juanen_US
dc.contributor.authorQi, Yueen_US
dc.contributor.authorWang, Chaoen_US
dc.contributor.authorZong, Lilien_US
dc.contributor.authorTan, Choon-Hongen_US
dc.date.accessioned2022-10-17T04:26:08Z-
dc.date.available2022-10-17T04:26:08Z-
dc.date.issued2021-
dc.identifier.citationLi, S., Wang, S., Li, J., Qi, Y., Wang, C., Zong, L. & Tan, C. (2021). Monocationic cinchoninium catalyzed asymmetric oxohydroxylation of enoates. ACS Catalysis, 11(24), 15141-15148. https://dx.doi.org/10.1021/acscatal.1c04849en_US
dc.identifier.issn2155-5435en_US
dc.identifier.urihttps://hdl.handle.net/10356/162373-
dc.description.abstractAsymmetric dihydroxylation and epoxidation are well-developed and widely used approaches to introduce chiral oxygenated functional groups with an alkene substrate. However, oxohydroxylation of an alkene, furnishing adjacent oxo and hydroxy groups, is less explored. In this paper, asymmetric oxohydroxylation of α-alkyl enoates with potassium permanganate catalyzed by monocationic quaternary ammonium salts derived from cinchona alkaloid is reported. A series of α-hydroxy-β-keto esters were obtained in up to 96% yield and 98% ee under user-friendly conditions. Synthetic application of oxohydroxylation was demonstrated in the synthesis of key chiral building blocks for thapsigargin and camptothecin synthesis. Control experiments indicated that, compared with tetrabutylammonium, monocationic chiral cinchoninium has a dramatic rate acceleration effect on catalytic permanganate oxidation.en_US
dc.language.isoenen_US
dc.relation.ispartofACS Catalysisen_US
dc.rights© 2021 American Chemical Society. All rights reserved.en_US
dc.subjectScience::Chemistryen_US
dc.titleMonocationic cinchoninium catalyzed asymmetric oxohydroxylation of enoatesen_US
dc.typeJournal Articleen
dc.contributor.schoolSchool of Physical and Mathematical Sciencesen_US
dc.identifier.doi10.1021/acscatal.1c04849-
dc.identifier.scopus2-s2.0-85121045994-
dc.identifier.issue24en_US
dc.identifier.volume11en_US
dc.identifier.spage15141en_US
dc.identifier.epage15148en_US
dc.subject.keywordsAsymmetric Oxohydroxylationen_US
dc.subject.keywordsOxidationen_US
dc.description.acknowledgementWe gratefully acknowledge the financial support from Nanjing Tech University (Start-up Grant No. 38274017100), National Natural Science Foundation of China (Nos. 21901115 and 21802018), Natural Science Foundation of Jiangsu Province (No. BK20190663), High-level Innovation and Entrepreneurship Talents Introduction Program of Jiangsu Province of China.en_US
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