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

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2025

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Zhang, Miaomiao
Yang, Yue
Li, Tong
Qiu, Yongshun
Li, Tianlu

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https://doi.org/10.1021/acs.orglett.5c02580
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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.5c02580

Zusammenfassung

Herein, 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.

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ISO 690ZHANG, 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.5c02580
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}
}
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    <dcterms:abstract>Herein, 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.</dcterms:abstract>
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