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Nucleophile-dependent regio- and stereoselective ring opening of 1-azoniabicyclo[3.1.0]hexane tosylate

(2014) CHEMISTRY-AN ASIAN JOURNAL. 9(4). p.1060-1067
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Abstract
1-[(1R)-(1-Phenylethyl)]-1-azoniabicyclo[3.1.0]hexane tosylate was generated as a stable bicyclic aziridinium salt from the corresponding 2-(3-hydroxypropyl)aziridine upon reaction with p-toluenesulfonyl anhydride. This bicyclic aziridinium ion was then treated with various nucleophiles including halides, azide, acetate, and cyanide in CH3CN to afford either piperidines or pyrrolidines through regio- and stereoselective ring opening, mediated by the characteristics of the applied nucleophile. On the basis of DFT calculations, ring-opening reactions under thermodynamic control yield piperidines, whereas reactions under kinetic control can yield both piperidines and pyrrolidines depending on the activation energies for both pathways.
Keywords
TRANSFORMATION, SALTS, REACTIVITY, CYCLIC AMINES, PIPERIDINES, EXPANSION, THEORETICAL RATIONALIZATION, CHIRAL AZIRIDINES, ring opening, ELECTROPHILE-INDUCED CYCLIZATION, SUBSTITUTED 3-FLUOROPIPERIDINES, ring expansion, nucleophilic substitution, heterocycles, density functional theory calculations, aziridines

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Citation

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MLA
Ji, Mi-Kyung, Dietmar Hertsen, Doo-Ha Yoon, et al. “Nucleophile-dependent Regio- and Stereoselective Ring Opening of 1-azoniabicyclo[3.1.0]hexane Tosylate.” CHEMISTRY-AN ASIAN JOURNAL 9.4 (2014): 1060–1067. Print.
APA
Ji, M.-K., Hertsen, D., Yoon, D.-H., Eum, H., Goossens, H., Waroquier, M., Van Speybroeck, V., et al. (2014). Nucleophile-dependent regio- and stereoselective ring opening of 1-azoniabicyclo[3.1.0]hexane tosylate. CHEMISTRY-AN ASIAN JOURNAL, 9(4), 1060–1067.
Chicago author-date
Ji, Mi-Kyung, Dietmar Hertsen, Doo-Ha Yoon, Heesung Eum, Hannelore Goossens, Michel Waroquier, Veronique Van Speybroeck, Matthias D’hooghe, Norbert De Kimpe, and Hyun-Joon Ha. 2014. “Nucleophile-dependent Regio- and Stereoselective Ring Opening of 1-azoniabicyclo[3.1.0]hexane Tosylate.” Chemistry-an Asian Journal 9 (4): 1060–1067.
Chicago author-date (all authors)
Ji, Mi-Kyung, Dietmar Hertsen, Doo-Ha Yoon, Heesung Eum, Hannelore Goossens, Michel Waroquier, Veronique Van Speybroeck, Matthias D’hooghe, Norbert De Kimpe, and Hyun-Joon Ha. 2014. “Nucleophile-dependent Regio- and Stereoselective Ring Opening of 1-azoniabicyclo[3.1.0]hexane Tosylate.” Chemistry-an Asian Journal 9 (4): 1060–1067.
Vancouver
1.
Ji M-K, Hertsen D, Yoon D-H, Eum H, Goossens H, Waroquier M, et al. Nucleophile-dependent regio- and stereoselective ring opening of 1-azoniabicyclo[3.1.0]hexane tosylate. CHEMISTRY-AN ASIAN JOURNAL. 2014;9(4):1060–7.
IEEE
[1]
M.-K. Ji et al., “Nucleophile-dependent regio- and stereoselective ring opening of 1-azoniabicyclo[3.1.0]hexane tosylate,” CHEMISTRY-AN ASIAN JOURNAL, vol. 9, no. 4, pp. 1060–1067, 2014.
@article{5712490,
  abstract     = {1-[(1R)-(1-Phenylethyl)]-1-azoniabicyclo[3.1.0]hexane tosylate was generated as a stable bicyclic aziridinium salt from the corresponding 2-(3-hydroxypropyl)aziridine upon reaction with p-toluenesulfonyl anhydride. This bicyclic aziridinium ion was then treated with various nucleophiles including halides, azide, acetate, and cyanide in CH3CN to afford either piperidines or pyrrolidines through regio- and stereoselective ring opening, mediated by the characteristics of the applied nucleophile. On the basis of DFT calculations, ring-opening reactions under thermodynamic control yield piperidines, whereas reactions under kinetic control can yield both piperidines and pyrrolidines depending on the activation energies for both pathways.},
  author       = {Ji, Mi-Kyung and Hertsen, Dietmar and Yoon, Doo-Ha and Eum, Heesung and Goossens, Hannelore and Waroquier, Michel and Van Speybroeck, Veronique and D'hooghe, Matthias and De Kimpe, Norbert and Ha, Hyun-Joon},
  issn         = {1861-4728},
  journal      = {CHEMISTRY-AN ASIAN JOURNAL},
  keywords     = {TRANSFORMATION,SALTS,REACTIVITY,CYCLIC AMINES,PIPERIDINES,EXPANSION,THEORETICAL RATIONALIZATION,CHIRAL AZIRIDINES,ring opening,ELECTROPHILE-INDUCED CYCLIZATION,SUBSTITUTED 3-FLUOROPIPERIDINES,ring expansion,nucleophilic substitution,heterocycles,density functional theory calculations,aziridines},
  language     = {eng},
  number       = {4},
  pages        = {1060--1067},
  title        = {Nucleophile-dependent regio- and stereoselective ring opening of 1-azoniabicyclo[3.1.0]hexane tosylate},
  url          = {http://dx.doi.org/10.1002/asia.201301551},
  volume       = {9},
  year         = {2014},
}

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