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Selective synthesis of cis- and trans-2-(methyl/phenyl)-3-(trifluoromethyl)aziridines and their regio- and stereospecific ring opening

Matthias Moens (UGent) , Norbert De Kimpe (UGent) and Matthias D'hooghe (UGent)
(2014) JOURNAL OF ORGANIC CHEMISTRY. 79(12). p.5558-5568
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Abstract
A convenient and stereoselective approach toward cis- and trans-1-alkyl-2-(methyl/phenyl)-3-(trifluoromethyl)aziridines was developed starting from the corresponding alpha,alpha,alpha-trifluoroketones via imination, a-chlorination, and hydride-induced ring closure. The reactivity of these newly synthesized nonactivated alpha-CF3-aziridines was evaluated by applying N-protonation or N-alkylation to effect regio- and stereospecific aziridine ring opening by oxygen, halogen, sulfur, and nitrogen nucleophiles. Furthermore, nonactivated alpha-CF3-aziridines were easily transformed into their activated analogues by replacing the N-benzyl protecting group with a N-tosyl group, rendering.
Keywords
MEDICINAL CHEMISTRY, N-TOSYL AZIRIDINES, STEREOSELECTIVE-SYNTHESIS, CF3-SUBSTITUTED AZIRIDINES, SUBSTITUTED AZIRIDINES, EFFICIENT SYNTHESIS, FLUORINE, DERIVATIVES, HALOGENATED IMINO COMPOUNDS, ALPHA-AMINO-ACIDS

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Citation

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MLA
Moens, Matthias, Norbert De Kimpe, and Matthias D’hooghe. “Selective Synthesis of Cis- and Trans-2-(methyl/phenyl)-3-(trifluoromethyl)aziridines and Their Regio- and Stereospecific Ring Opening.” JOURNAL OF ORGANIC CHEMISTRY 79.12 (2014): 5558–5568. Print.
APA
Moens, Matthias, De Kimpe, N., & D’hooghe, M. (2014). Selective synthesis of cis- and trans-2-(methyl/phenyl)-3-(trifluoromethyl)aziridines and their regio- and stereospecific ring opening. JOURNAL OF ORGANIC CHEMISTRY, 79(12), 5558–5568.
Chicago author-date
Moens, Matthias, Norbert De Kimpe, and Matthias D’hooghe. 2014. “Selective Synthesis of Cis- and Trans-2-(methyl/phenyl)-3-(trifluoromethyl)aziridines and Their Regio- and Stereospecific Ring Opening.” Journal of Organic Chemistry 79 (12): 5558–5568.
Chicago author-date (all authors)
Moens, Matthias, Norbert De Kimpe, and Matthias D’hooghe. 2014. “Selective Synthesis of Cis- and Trans-2-(methyl/phenyl)-3-(trifluoromethyl)aziridines and Their Regio- and Stereospecific Ring Opening.” Journal of Organic Chemistry 79 (12): 5558–5568.
Vancouver
1.
Moens M, De Kimpe N, D’hooghe M. Selective synthesis of cis- and trans-2-(methyl/phenyl)-3-(trifluoromethyl)aziridines and their regio- and stereospecific ring opening. JOURNAL OF ORGANIC CHEMISTRY. 2014;79(12):5558–68.
IEEE
[1]
M. Moens, N. De Kimpe, and M. D’hooghe, “Selective synthesis of cis- and trans-2-(methyl/phenyl)-3-(trifluoromethyl)aziridines and their regio- and stereospecific ring opening,” JOURNAL OF ORGANIC CHEMISTRY, vol. 79, no. 12, pp. 5558–5568, 2014.
@article{5757778,
  abstract     = {A convenient and stereoselective approach toward cis- and trans-1-alkyl-2-(methyl/phenyl)-3-(trifluoromethyl)aziridines was developed starting from the corresponding alpha,alpha,alpha-trifluoroketones via imination, a-chlorination, and hydride-induced ring closure. The reactivity of these newly synthesized nonactivated alpha-CF3-aziridines was evaluated by applying N-protonation or N-alkylation to effect regio- and stereospecific aziridine ring opening by oxygen, halogen, sulfur, and nitrogen nucleophiles. Furthermore, nonactivated alpha-CF3-aziridines were easily transformed into their activated analogues by replacing the N-benzyl protecting group with a N-tosyl group, rendering.},
  author       = {Moens, Matthias and De Kimpe, Norbert and D'hooghe, Matthias},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {MEDICINAL CHEMISTRY,N-TOSYL AZIRIDINES,STEREOSELECTIVE-SYNTHESIS,CF3-SUBSTITUTED AZIRIDINES,SUBSTITUTED AZIRIDINES,EFFICIENT SYNTHESIS,FLUORINE,DERIVATIVES,HALOGENATED IMINO COMPOUNDS,ALPHA-AMINO-ACIDS},
  language     = {eng},
  number       = {12},
  pages        = {5558--5568},
  title        = {Selective synthesis of cis- and trans-2-(methyl/phenyl)-3-(trifluoromethyl)aziridines and their regio- and stereospecific ring opening},
  url          = {http://dx.doi.org/10.1021/jo5007448},
  volume       = {79},
  year         = {2014},
}

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