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Nucleophile-directed selective transformation of cis-1-tosyl-2-toxyloxymethyl-3-(trifluoromethyl)aziridine into aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines

(2013) CHEMISTRY-A EUROPEAN JOURNAL. 19(19). p.5966-5971
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Abstract
A five-step procedure for the synthesis of cis-1-tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine was developed, starting from 1-ethoxy-2,2,2-trifluoroethanol, involving imination, aziridination, ester reduction, hydrogenation, and N-, O-ditosylation steps. Further synthetic elaborations revealed a remarkable difference in the reactivity of cis-1-tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine with respect to aromatic sulfur and oxygen nucleophiles, thus enabling the selective deployment of this versatile substrate as a building block for the synthesis of functionalized aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines.
Keywords
ALPHA(1)-ADRENORECEPTOR SUBTYPES, STEREOSELECTIVE-SYNTHESIS, ORGANOFLUORINE CHEMISTRY, AMINO ACIDS, FLUORINE, DERIVATIVES, DESIGN, aziridines, heterocycles, oxygen, ring expansion, sulfur, RING-OPENING REACTIONS, ASYMMETRIC-SYNTHESIS, MEDICINAL CHEMISTRY

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Chicago
Kenis, Sara, Matthias D’hooghe, Guido Verniest, Maaike Reybroeck, Tuyet Anh Dang Thi, Chinh Pham The, Tham Thi Pham, Karl W Törnroos, Nguyen Van Tuyen, and Norbert De Kimpe. 2013. “Nucleophile-directed Selective Transformation of Cis-1-tosyl-2-toxyloxymethyl-3-(trifluoromethyl)aziridine into Aziridines, Azetidines, and Benzo-fused Dithianes, Oxathianes, Dioxanes, and (thio)morpholines.” Chemistry-a European Journal 19 (19): 5966–5971.
APA
Kenis, S., D’hooghe, M., Verniest, G., Reybroeck, M., Thi, T. A. D., The, C. P., Pham, T. T., et al. (2013). Nucleophile-directed selective transformation of cis-1-tosyl-2-toxyloxymethyl-3-(trifluoromethyl)aziridine into aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines. CHEMISTRY-A EUROPEAN JOURNAL, 19(19), 5966–5971.
Vancouver
1.
Kenis S, D’hooghe M, Verniest G, Reybroeck M, Thi TAD, The CP, et al. Nucleophile-directed selective transformation of cis-1-tosyl-2-toxyloxymethyl-3-(trifluoromethyl)aziridine into aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines. CHEMISTRY-A EUROPEAN JOURNAL. 2013;19(19):5966–71.
MLA
Kenis, Sara, Matthias D’hooghe, Guido Verniest, et al. “Nucleophile-directed Selective Transformation of Cis-1-tosyl-2-toxyloxymethyl-3-(trifluoromethyl)aziridine into Aziridines, Azetidines, and Benzo-fused Dithianes, Oxathianes, Dioxanes, and (thio)morpholines.” CHEMISTRY-A EUROPEAN JOURNAL 19.19 (2013): 5966–5971. Print.
@article{4173486,
  abstract     = {A five-step procedure for the synthesis of cis-1-tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine was developed, starting from 1-ethoxy-2,2,2-trifluoroethanol, involving imination, aziridination, ester reduction, hydrogenation, and N-, O-ditosylation steps. Further synthetic elaborations revealed a remarkable difference in the reactivity of cis-1-tosyl-2-tosyloxymethyl-3-(trifluoromethyl)aziridine with respect to aromatic sulfur and oxygen nucleophiles, thus enabling the selective deployment of this versatile substrate as a building block for the synthesis of functionalized aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines.},
  author       = {Kenis, Sara and D'hooghe, Matthias and Verniest, Guido and Reybroeck, Maaike and Thi, Tuyet Anh Dang and The, Chinh Pham and Pham, Tham Thi and T{\"o}rnroos, Karl W and Tuyen, Nguyen Van and De Kimpe, Norbert},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  language     = {eng},
  number       = {19},
  pages        = {5966--5971},
  title        = {Nucleophile-directed selective transformation of cis-1-tosyl-2-toxyloxymethyl-3-(trifluoromethyl)aziridine into aziridines, azetidines, and benzo-fused dithianes, oxathianes, dioxanes, and (thio)morpholines},
  url          = {http://dx.doi.org/10.1002/chem.201204485},
  volume       = {19},
  year         = {2013},
}

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