The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Enantioselective Ring Opening of Epoxides by Fluoride Anion Promoted by a Cooperative Dual-Catalyst System
Abstract
An enantioselective method for the synthesis of beta-fluoroalcohols by catalytic nucleophilic fluorination of epoxides is described. Mild reaction conditions and high selectivity are made possible by the use of benzoyl fluoride as a soluble, latent source of fluoride anion. A chiral amine and chiral Lewis acid serve as cooperative catalysts for desymmetrizations of five- through eight-membered cyclic epoxides, affording products in up to 95% ee. The cocatalytic protocol is also effective for kinetic resolutions of racemic terminal epoxides, which proceed with k(rel) values as high as 300.
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Citations
Cites
Asymmetric Catalysis of Epoxide Ring-Opening Reactions
Jacobsen, E. N. (2000) · Accounts of Chemical Research · doi:10.1021/ar960061v · Cited by 1,261
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Motiwala, H. F., Armaly, A. M., Cacioppo, J. G., Coombs, T. C., Koehn, K. R. K., Norwood, V. M., & Aubé, J. (2022) · Chemical Reviews · doi:10.1021/acs.chemrev.1c00749 · Cited by 593
Transition-Metal-Catalyzed C–H Bond Activation for the Formation of C–C Bonds in Complex Molecules
Docherty, J. H., Lister, T. M., Mcarthur, G., Findlay, M. T., Domingo-Legarda, P., Kenyon, J., Choudhary, S., & Larrosa, I. (2023) · Chemical Reviews · doi:10.1021/acs.chemrev.2c00888 · Cited by 593
Oxidative Aliphatic C-H Fluorination with Fluoride Ion Catalyzed by a Manganese Porphyrin
Liu, W., Huang, X., Cheng, M.-J., Nielsen, R. J., Goddard, W. A., & Groves, J. T. (2012) · Science · doi:10.1126/science.1222327 · Cited by 566
Xia, J.-B., Zhu, C., & Chen, C. (2013) · Journal of the American Chemical Society · doi:10.1021/ja410815u · Cited by 560
Ford, D. D., Nielsen, L. P. C., Zuend, S. J., Musgrave, C. B., & Jacobsen, E. N. (2013) · Journal of the American Chemical Society · doi:10.1021/ja408027p · Cited by 138
Metadata
- Authors
- Kalow, J. A., & Doyle, A. G.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-02-17
- Volume
- 132
- Issue
- 10
- Pages
- 3268-3269
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1977024991
- Cited by
- 281
- References
- 1
- FWCI
- 16.44
- Type
- journal article
- Language
- en
- Open access
- closed
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
