Fluoride-Effect-Directed Catalyst-Controlled Regioselective Acylation of Carbohydrate Diols and Triols

Kurzanzeige
dc.contributor.authorZhang, Miaomiao
dc.contributor.authorYang, Yue
dc.contributor.authorLi, Tong
dc.contributor.authorQiu, Yongshun
dc.contributor.authorLi, Tianlu
dc.contributor.authorSchmidt, Richard R.
dc.contributor.authorPeng, Peng
dc.date.accessioned2025-10-07T10:46:10Z
dc.date.available2025-10-07T10:46:10Z
dc.date.issued2025-07-27
dc.description.abstractHerein, we report that acyl fluorides enable the switchable selective acylation of vicinal 1,2-cis-diol motifs in carbohydrates. While DMAP as a catalyst directs equatorial acylation, DBU highly promotes the thermodynamically unfavorable axial O-acylation, reversing conventional preferences. NMR studies and DFT calculations indicate that triple hydrogen bonding governs this unusual regioselectivity. This method eliminates the need for metal salts, elaborate catalysts, or complex ligands, offering a practical and efficient platform for regioselective carbohydrate transformation and synthesis.
dc.description.versionpublisheddeu
dc.identifier.doi10.1021/acs.orglett.5c02580
dc.identifier.urihttps://kops.uni-konstanz.de/handle/123456789/74704
dc.language.isoeng
dc.subject.ddc540
dc.titleFluoride-Effect-Directed Catalyst-Controlled Regioselective Acylation of Carbohydrate Diols and Triolseng
dc.typeJOURNAL_ARTICLE
dspace.entity.typePublication
kops.citation.bibtex
@article{Zhang2025-07-27Fluor-74704,
  title={Fluoride-Effect-Directed Catalyst-Controlled Regioselective Acylation of Carbohydrate Diols and Triols},
  year={2025},
  doi={10.1021/acs.orglett.5c02580},
  number={31},
  volume={27},
  issn={1523-7060},
  journal={Organic Letters},
  pages={8624--8630},
  author={Zhang, Miaomiao and Yang, Yue and Li, Tong and Qiu, Yongshun and Li, Tianlu and Schmidt, Richard R. and Peng, Peng}
}
kops.citation.iso690ZHANG, Miaomiao, Yue YANG, Tong LI, Yongshun QIU, Tianlu LI, Richard R. SCHMIDT, Peng PENG, 2025. Fluoride-Effect-Directed Catalyst-Controlled Regioselective Acylation of Carbohydrate Diols and Triols. In: Organic Letters. American Chemical Society (ACS). 2025, 27(31), S. 8624-8630. ISSN 1523-7060. eISSN 1523-7052. Verfügbar unter: doi: 10.1021/acs.orglett.5c02580deu
kops.citation.iso690ZHANG, Miaomiao, Yue YANG, Tong LI, Yongshun QIU, Tianlu LI, Richard R. SCHMIDT, Peng PENG, 2025. Fluoride-Effect-Directed Catalyst-Controlled Regioselective Acylation of Carbohydrate Diols and Triols. In: Organic Letters. American Chemical Society (ACS). 2025, 27(31), pp. 8624-8630. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.5c02580eng
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kops.sourcefield.plainOrganic Letters. American Chemical Society (ACS). 2025, 27(31), pp. 8624-8630. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.5c02580eng
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