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Design, Synthesis, and Evaluation of a Novel Class of Enantioselective Electrophilic Fluorinating Agents: N-Fluoro Ammonium Salts of cinchona Alkaloids (F-CA-BF4)
Abstract
The first enantiopure N-fluoro quaternary ammonium salts of cinchona alkaloids as enantioselective fluorinating agents are reported. A one-step transfer-fluorination on the naturally occurring cinchona alkaloids gave the fluorinating agents F-CA-BF(4). This new generation of fluorinating agents exhibited asymmetric induction up to 61% on fluorination of enolates and silyl enol ethers of 2-methyl-1-tetralone.
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Citations
Cited by
The Many Roles for Fluorine in Medicinal Chemistry
Hagmann, W. K. (2008) · Journal of Medicinal Chemistry · doi:10.1021/jm800219f · Cited by 3,578
Update 1 of: Asymmetric Fluorination, Trifluoromethylation, and Perfluoroalkylation Reactions
Ma, J.-A., & Cahard, D. (2008) · Chemical Reviews · doi:10.1021/cr800221v · Cited by 892
Self-citationZhu, Y., Han, J., Wang, J., Shibata, N., Sodeoka, M., Soloshonok, V. A., Coelho, J. A. S., & Toste, F. D. (2018) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00778 · Cited by 640
Asymmetric Electrophilic Fluorination Using an Anionic Chiral Phase-Transfer Catalyst
Rauniyar, V., Lackner, A. D., Hamilton, G. L., & Toste, F. D. (2011) · Science · doi:10.1126/science.1213918 · Cited by 503
More Sustainable Approaches for the Synthesis of N-Based Heterocycles
Candeias, N. R., Branco, L. C., Gois, P. M. P., Afonso, C. A. M., & Trindade, A. F. (2009) · Chemical Reviews · doi:10.1021/cr800462w · Cited by 403
Metadata
- Authors
- Cahard, D., Audouard, C., Plaquevent, J.-C., & Roques, N.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2000-10-24
- Volume
- 2
- Issue
- 23
- Pages
- 3699-3701
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2951953897
- Cited by
- 179
- References
- 0
- FWCI
- 8.53
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Design, Synthesis, and Evaluation of a Novel Class of Enantioselective Electrophilic Fluorinating Agents: N-Fluoro Ammonium Salts of cinchona Alkaloids (F-CA-BF4). https://app.cochat.ai/papers/10.1021/ol006610l
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- Cahard, D., Audouard, C., Plaquevent, J.-C., & Roques, N. (2000). Design, Synthesis, and Evaluation of a Novel Class of Enantioselective Electrophilic Fluorinating Agents: N-Fluoro Ammonium Salts of cinchona Alkaloids (F-CA-BF4). Organic Letters. https://doi.org/10.1021/ol006610l
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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