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New entries toward 3,3-difluoropiperidines

(2008) JOURNAL OF ORGANIC CHEMISTRY. 73(14). p.5458-5461
Author
Organization
Abstract
Difluoropiperidines attract considerable interest from organic and medicinal chemists, but their synthesis is often problematic. This paper describes a new synthetic pathway toward valuable 3,3-difluoropiperidines starting from suitable 6-chloro-alpha,alpha-difluoroimines. The latter imines can be synthesized via electrophilic fluorination of the corresponding delta-chloroimines using NFSI (N-fluorodibenzenesulfonimide) in acetonitrile. After hydride reduction of the imino bond and subsequent intramolecular substitution of the chloride atom, new 3,3-difluoropiperidines were obtained in good yields. In addition, this methodology was applied to establish the first synthesis of N-protected 3,3-difluoropipecolic acid, a new fluorinated amino acid.
Keywords
MEDICINAL CHEMISTRY, BIOLOGICAL EVALUATION, EFFICIENT SYNTHESIS, FLUORINE, PYRIDINES, IMINES, ANIONS, ACIDS

Citation

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MLA
Verniest, Guido, et al. “New Entries toward 3,3-Difluoropiperidines.” JOURNAL OF ORGANIC CHEMISTRY, vol. 73, no. 14, 2008, pp. 5458–61, doi:10.1021/jo800768q.
APA
Verniest, G., Surmont, R., Van Hende, E., Deweweire, A., Deroose, F., Thuring, J. W., & De Kimpe, N. (2008). New entries toward 3,3-difluoropiperidines. JOURNAL OF ORGANIC CHEMISTRY, 73(14), 5458–5461. https://doi.org/10.1021/jo800768q
Chicago author-date
Verniest, Guido, Riccardo Surmont, Eva Van Hende, Arvid Deweweire, Frederik Deroose, Jan Willen Thuring, and Norbert De Kimpe. 2008. “New Entries toward 3,3-Difluoropiperidines.” JOURNAL OF ORGANIC CHEMISTRY 73 (14): 5458–61. https://doi.org/10.1021/jo800768q.
Chicago author-date (all authors)
Verniest, Guido, Riccardo Surmont, Eva Van Hende, Arvid Deweweire, Frederik Deroose, Jan Willen Thuring, and Norbert De Kimpe. 2008. “New Entries toward 3,3-Difluoropiperidines.” JOURNAL OF ORGANIC CHEMISTRY 73 (14): 5458–5461. doi:10.1021/jo800768q.
Vancouver
1.
Verniest G, Surmont R, Van Hende E, Deweweire A, Deroose F, Thuring JW, et al. New entries toward 3,3-difluoropiperidines. JOURNAL OF ORGANIC CHEMISTRY. 2008;73(14):5458–61.
IEEE
[1]
G. Verniest et al., “New entries toward 3,3-difluoropiperidines,” JOURNAL OF ORGANIC CHEMISTRY, vol. 73, no. 14, pp. 5458–5461, 2008.
@article{631206,
  abstract     = {{Difluoropiperidines attract considerable interest from organic and medicinal chemists, but their synthesis is often problematic. This paper describes a new synthetic pathway toward valuable 3,3-difluoropiperidines starting from suitable 6-chloro-alpha,alpha-difluoroimines. The latter imines can be synthesized via electrophilic fluorination of the corresponding delta-chloroimines using NFSI (N-fluorodibenzenesulfonimide) in acetonitrile. After hydride reduction of the imino bond and subsequent intramolecular substitution of the chloride atom, new 3,3-difluoropiperidines were obtained in good yields. In addition, this methodology was applied to establish the first synthesis of N-protected 3,3-difluoropipecolic acid, a new fluorinated amino acid.}},
  author       = {{Verniest, Guido and Surmont, Riccardo and Van Hende, Eva and Deweweire, Arvid and Deroose, Frederik and Thuring, Jan Willen and De Kimpe, Norbert}},
  issn         = {{0022-3263}},
  journal      = {{JOURNAL OF ORGANIC CHEMISTRY}},
  keywords     = {{MEDICINAL CHEMISTRY,BIOLOGICAL EVALUATION,EFFICIENT SYNTHESIS,FLUORINE,PYRIDINES,IMINES,ANIONS,ACIDS}},
  language     = {{eng}},
  number       = {{14}},
  pages        = {{5458--5461}},
  title        = {{New entries toward 3,3-difluoropiperidines}},
  url          = {{http://dx.doi.org/10.1021/jo800768q}},
  volume       = {{73}},
  year         = {{2008}},
}

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