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Highly asymmetric aldol reaction of isatins and ketones catalyzed by chiral bifunctional primary-amine organocatalyst on water
Lv, Xiao-Xiong1; Liu, Ning1; Chen, Fei1; Zhang, Hao1; Du, Zhi-Hong1; Wang, Pei2; Yuan, Meng3; Da, Chao Shan3
2023-11-08
Online publication date2023-10
Source PublicationORGANIC & BIOMOLECULAR CHEMISTRY   Impact Factor & Quartile
ISSN1477-0520 ; 1477-0539
EISSN1477-0539
Volume21Issue:43Pages:8695-8701
page numbers7
AbstractHerein, we have reported an environmentally friendly asymmetric aldol reaction between isatins and ketones catalyzed by double-hydrogen-bonded primary amine organocatalysts on water under mild conditions. Enantioenriched 3-hydroxy-2-oxindoles were obtained in high yields (up to 99%) and excellent stereoselectivities (up to 99 : 1 dr and 99% ee) under optimal conditions. Furthermore, the model reaction involving isatin and cyclohexanone was successfully scaled to 10 mmol with no reduction in yield or stereoselectivity. In addition, the catalyst was recovered via simple filtration and was subsequently reused on water, which highlights its good application potential.
PublisherROYAL SOC CHEMISTRY
DOI10.1039/d3ob01227a
Indexed BySCIE ; IC
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:001086275300001
Original Document TypeArticle
PMID 37861676
Citation statistics
Document Type期刊论文
Identifierhttps://ir.lzu.edu.cn/handle/262010/568850
Collection兰州大学
Corresponding AuthorLiu, Ning; Du, Zhi-Hong
Affiliation
1.Shihezi Univ, Sch Chem & Chem Engn, State Key Lab Incubat Base Green Proc Chem Engn, North 4th Rd, Shihezi 832003, Xinjiang, Peoples R China;
2.Ningxia Med Univ, Sch Basic Med Sci, Yinchuan, Peoples R China;
3.Lanzhou Univ, Inst Biochem & Mol Biol, Sch Life Sci, Lanzhou 730000, Peoples R China
Recommended Citation
GB/T 7714
Lv, Xiao-Xiong,Liu, Ning,Chen, Fei,et al. Highly asymmetric aldol reaction of isatins and ketones catalyzed by chiral bifunctional primary-amine organocatalyst on water[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2023,21(43):8695-8701.
APA Lv, Xiao-Xiong.,Liu, Ning.,Chen, Fei.,Zhang, Hao.,Du, Zhi-Hong.,...&Da, Chao Shan.(2023).Highly asymmetric aldol reaction of isatins and ketones catalyzed by chiral bifunctional primary-amine organocatalyst on water.ORGANIC & BIOMOLECULAR CHEMISTRY,21(43),8695-8701.
MLA Lv, Xiao-Xiong,et al."Highly asymmetric aldol reaction of isatins and ketones catalyzed by chiral bifunctional primary-amine organocatalyst on water".ORGANIC & BIOMOLECULAR CHEMISTRY 21.43(2023):8695-8701.
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