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Selective synthesis of functionalized trifluoromethylated pyrrolidines, piperidines, and azepanes starting from 1-tosyl-2-(trifluoromethyl)aziridine

Jeroen Dolfen (UGent) , Sara Kenis (UGent) , Kristof Van Hecke (UGent) , Norbert De Kimpe (UGent) and Matthias D'hooghe (UGent)
(2014) CHEMISTRY-A EUROPEAN JOURNAL. 20(34). p.10650-10653
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Abstract
This paper reports on the generation and alkylation of the 1-tosyl-2-(trifluoromethyl)aziridin-2-yl anion with omega,omega'-dihaloalkanes, followed by a novel ring-expansion protocol toward 2-CF3-pyrrolidines, 2-CF3-piperidines, and 3-CF3-azepanes. A variety of halogen, oxygen, nitrogen, sulfur, and carbon nucleophiles was used to trigger this ring rearrangement, resulting in CF3-azaheterocycles bearing different types of functionalized side chains.
Keywords
GENERATION, REACTIVITY, CONSTRUCTION, TRANSFORMATION, CYCLOADDITION, FLUORINE, AZIRIDINYL ANIONS, AMINO-ACIDS, RING-OPENING REACTIONS, MEDICINAL CHEMISTRY, trifluoromethyl, piperidines, pyrrolidines, aziridines, aziridinyl anions, azepanes

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MLA
Dolfen, Jeroen, Sara Kenis, Kristof Van Hecke, et al. “Selective Synthesis of Functionalized Trifluoromethylated Pyrrolidines, Piperidines, and Azepanes Starting from 1-tosyl-2-(trifluoromethyl)aziridine.” CHEMISTRY-A EUROPEAN JOURNAL 20.34 (2014): 10650–10653. Print.
APA
Dolfen, J., Kenis, S., Van Hecke, K., De Kimpe, N., & D’hooghe, M. (2014). Selective synthesis of functionalized trifluoromethylated pyrrolidines, piperidines, and azepanes starting from 1-tosyl-2-(trifluoromethyl)aziridine. CHEMISTRY-A EUROPEAN JOURNAL, 20(34), 10650–10653.
Chicago author-date
Dolfen, Jeroen, Sara Kenis, Kristof Van Hecke, Norbert De Kimpe, and Matthias D’hooghe. 2014. “Selective Synthesis of Functionalized Trifluoromethylated Pyrrolidines, Piperidines, and Azepanes Starting from 1-tosyl-2-(trifluoromethyl)aziridine.” Chemistry-a European Journal 20 (34): 10650–10653.
Chicago author-date (all authors)
Dolfen, Jeroen, Sara Kenis, Kristof Van Hecke, Norbert De Kimpe, and Matthias D’hooghe. 2014. “Selective Synthesis of Functionalized Trifluoromethylated Pyrrolidines, Piperidines, and Azepanes Starting from 1-tosyl-2-(trifluoromethyl)aziridine.” Chemistry-a European Journal 20 (34): 10650–10653.
Vancouver
1.
Dolfen J, Kenis S, Van Hecke K, De Kimpe N, D’hooghe M. Selective synthesis of functionalized trifluoromethylated pyrrolidines, piperidines, and azepanes starting from 1-tosyl-2-(trifluoromethyl)aziridine. CHEMISTRY-A EUROPEAN JOURNAL. 2014;20(34):10650–3.
IEEE
[1]
J. Dolfen, S. Kenis, K. Van Hecke, N. De Kimpe, and M. D’hooghe, “Selective synthesis of functionalized trifluoromethylated pyrrolidines, piperidines, and azepanes starting from 1-tosyl-2-(trifluoromethyl)aziridine,” CHEMISTRY-A EUROPEAN JOURNAL, vol. 20, no. 34, pp. 10650–10653, 2014.
@article{4443118,
  abstract     = {This paper reports on the generation and alkylation of the 1-tosyl-2-(trifluoromethyl)aziridin-2-yl anion with omega,omega'-dihaloalkanes, followed by a novel ring-expansion protocol toward 2-CF3-pyrrolidines, 2-CF3-piperidines, and 3-CF3-azepanes. A variety of halogen, oxygen, nitrogen, sulfur, and carbon nucleophiles was used to trigger this ring rearrangement, resulting in CF3-azaheterocycles bearing different types of functionalized side chains.},
  author       = {Dolfen, Jeroen and Kenis, Sara and Van Hecke, Kristof and De Kimpe, Norbert and D'hooghe, Matthias},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keywords     = {GENERATION,REACTIVITY,CONSTRUCTION,TRANSFORMATION,CYCLOADDITION,FLUORINE,AZIRIDINYL ANIONS,AMINO-ACIDS,RING-OPENING REACTIONS,MEDICINAL CHEMISTRY,trifluoromethyl,piperidines,pyrrolidines,aziridines,aziridinyl anions,azepanes},
  language     = {eng},
  number       = {34},
  pages        = {10650--10653},
  title        = {Selective synthesis of functionalized trifluoromethylated pyrrolidines, piperidines, and azepanes starting from 1-tosyl-2-(trifluoromethyl)aziridine},
  url          = {http://dx.doi.org/10.1002/chem.201304759},
  volume       = {20},
  year         = {2014},
}

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