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Concise synthesis of 3-(aminomethyl)pyrrolizidines via an In(OTf)3-mediated ring rearrangement of 2-[2-(1-pyrrolin-2-yl)-alkyl]aziridines

Jeroen Dolfen (UGent) and Matthias D'hooghe (UGent)
(2017) SYNTHESIS-STUTTGART. 49(10). p.2215-2222
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Abstract
In this study, an efficient ring rearrangement of 2-[2-(1-pyrrolin-2-yl)alkyl]aziridines, prepared from 2-(bromomethyl) aziridines, toward novel trans-and cis-3-aminomethyl-substituted pyrrolizidines was developed. To that end, addition of In(OTf)(3) as an appropriate Lewis acid catalyst resulted in the formation of intermediate pyrrolizidinium salts via regioselective aziridine ring opening, which were then trapped by a hydride or cyanide nucleophile. Column chromatographic purification allowed the isolation of the major trans-isomers, exclusively.
Keywords
pyrrolizidines, aziridines, ring rearrangement, alpha-aminonitriles, In(OTf)(3), PYRROLIZIDINE ALKALOIDS, 1, 3-DIPOLAR CYCLOADDITIONS, TOXICITY

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Chicago
Dolfen, Jeroen, and Matthias D’hooghe. 2017. “Concise Synthesis of 3-(aminomethyl)pyrrolizidines via an In(OTf)3-mediated Ring Rearrangement of 2-[2-(1-pyrrolin-2-yl)-alkyl]aziridines.” Synthesis-stuttgart 49 (10): 2215–2222.
APA
Dolfen, J., & D’hooghe, M. (2017). Concise synthesis of 3-(aminomethyl)pyrrolizidines via an In(OTf)3-mediated ring rearrangement of 2-[2-(1-pyrrolin-2-yl)-alkyl]aziridines. SYNTHESIS-STUTTGART, 49(10), 2215–2222.
Vancouver
1.
Dolfen J, D’hooghe M. Concise synthesis of 3-(aminomethyl)pyrrolizidines via an In(OTf)3-mediated ring rearrangement of 2-[2-(1-pyrrolin-2-yl)-alkyl]aziridines. SYNTHESIS-STUTTGART. 2017;49(10):2215–22.
MLA
Dolfen, Jeroen, and Matthias D’hooghe. “Concise Synthesis of 3-(aminomethyl)pyrrolizidines via an In(OTf)3-mediated Ring Rearrangement of 2-[2-(1-pyrrolin-2-yl)-alkyl]aziridines.” SYNTHESIS-STUTTGART 49.10 (2017): 2215–2222. Print.
@article{8541115,
  abstract     = {In this study, an efficient ring rearrangement of 2-[2-(1-pyrrolin-2-yl)alkyl]aziridines, prepared from 2-(bromomethyl) aziridines, toward novel trans-and cis-3-aminomethyl-substituted pyrrolizidines was developed. To that end, addition of In(OTf)(3) as an appropriate Lewis acid catalyst resulted in the formation of intermediate pyrrolizidinium salts via regioselective aziridine ring opening, which were then trapped by a hydride or cyanide nucleophile. Column chromatographic purification allowed the isolation of the major trans-isomers, exclusively.},
  author       = {Dolfen, Jeroen and D'hooghe, Matthias},
  issn         = {0039-7881},
  journal      = {SYNTHESIS-STUTTGART},
  keywords     = {pyrrolizidines,aziridines,ring rearrangement,alpha-aminonitriles,In(OTf)(3),PYRROLIZIDINE ALKALOIDS,1,3-DIPOLAR CYCLOADDITIONS,TOXICITY},
  language     = {eng},
  number       = {10},
  pages        = {2215--2222},
  title        = {Concise synthesis of 3-(aminomethyl)pyrrolizidines via an In(OTf)3-mediated ring rearrangement of 2-[2-(1-pyrrolin-2-yl)-alkyl]aziridines},
  url          = {http://dx.doi.org/10.1055/s-0036-1588404},
  volume       = {49},
  year         = {2017},
}

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