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LiAlH4-Induced selective ring rearrangement of 2-(2-cyanoethyl)aziridines toward 2-(aminomethyl)pyrrolidines and 3-aminopiperidines as eligible heterocyclic building blocks

Jeroen Dolfen (UGent) , Karel Vervisch (UGent) , Norbert De Kimpe (UGent) and Matthias D'hooghe (UGent)
(2016) CHEMISTRY-A EUROPEAN JOURNAL. 22(14). p.4945-4951
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Abstract
2-(2-Cyanoethyl)aziridines and 2-aryl-3-(2-cyanoethyl)aziridines were deployed as substrates for an In(OTf)(3)-mediated regio- and stereoselective ring rearrangement upon treatment with LiAlH4, affording a variety of novel 2-(aminomethyl)pyrrolidines and 3-aminopiperidines, respectively. Further synthetic elaboration of the obtained 3-aminopiperidines resulted in the formation of a peculiar and unexplored conformationally constrained imidazolidinone and diketopiperazine scaffold.
Keywords
aziridines, bicyclic systems, Lewis acids, piperidines, pyrrolidines, ANDROGEN RECEPTOR MODULATORS, ASYMMETRIC-SYNTHESIS, CHIRAL AZIRIDINES, GAMMA-LACTONES, PIPERIDINES, PRECURSORS, EPOXIDES, SCAFFOLD, POTENT, TRANSFORMATION

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Citation

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MLA
Dolfen, Jeroen et al. “LiAlH4-Induced Selective Ring Rearrangement of 2-(2-cyanoethyl)aziridines Toward 2-(aminomethyl)pyrrolidines and 3-aminopiperidines as Eligible Heterocyclic Building Blocks.” CHEMISTRY-A EUROPEAN JOURNAL 22.14 (2016): 4945–4951. Print.
APA
Dolfen, J., Vervisch, K., De Kimpe, N., & D’hooghe, M. (2016). LiAlH4-Induced selective ring rearrangement of 2-(2-cyanoethyl)aziridines toward 2-(aminomethyl)pyrrolidines and 3-aminopiperidines as eligible heterocyclic building blocks. CHEMISTRY-A EUROPEAN JOURNAL, 22(14), 4945–4951.
Chicago author-date
Dolfen, Jeroen, Karel Vervisch, Norbert De Kimpe, and Matthias D’hooghe. 2016. “LiAlH4-Induced Selective Ring Rearrangement of 2-(2-cyanoethyl)aziridines Toward 2-(aminomethyl)pyrrolidines and 3-aminopiperidines as Eligible Heterocyclic Building Blocks.” Chemistry-a European Journal 22 (14): 4945–4951.
Chicago author-date (all authors)
Dolfen, Jeroen, Karel Vervisch, Norbert De Kimpe, and Matthias D’hooghe. 2016. “LiAlH4-Induced Selective Ring Rearrangement of 2-(2-cyanoethyl)aziridines Toward 2-(aminomethyl)pyrrolidines and 3-aminopiperidines as Eligible Heterocyclic Building Blocks.” Chemistry-a European Journal 22 (14): 4945–4951.
Vancouver
1.
Dolfen J, Vervisch K, De Kimpe N, D’hooghe M. LiAlH4-Induced selective ring rearrangement of 2-(2-cyanoethyl)aziridines toward 2-(aminomethyl)pyrrolidines and 3-aminopiperidines as eligible heterocyclic building blocks. CHEMISTRY-A EUROPEAN JOURNAL. 2016;22(14):4945–51.
IEEE
[1]
J. Dolfen, K. Vervisch, N. De Kimpe, and M. D’hooghe, “LiAlH4-Induced selective ring rearrangement of 2-(2-cyanoethyl)aziridines toward 2-(aminomethyl)pyrrolidines and 3-aminopiperidines as eligible heterocyclic building blocks,” CHEMISTRY-A EUROPEAN JOURNAL, vol. 22, no. 14, pp. 4945–4951, 2016.
@article{8500760,
  abstract     = {2-(2-Cyanoethyl)aziridines and 2-aryl-3-(2-cyanoethyl)aziridines were deployed as substrates for an In(OTf)(3)-mediated regio- and stereoselective ring rearrangement upon treatment with LiAlH4, affording a variety of novel 2-(aminomethyl)pyrrolidines and 3-aminopiperidines, respectively. Further synthetic elaboration of the obtained 3-aminopiperidines resulted in the formation of a peculiar and unexplored conformationally constrained imidazolidinone and diketopiperazine scaffold.},
  author       = {Dolfen, Jeroen and Vervisch, Karel and De Kimpe, Norbert and D'hooghe, Matthias},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keywords     = {aziridines,bicyclic systems,Lewis acids,piperidines,pyrrolidines,ANDROGEN RECEPTOR MODULATORS,ASYMMETRIC-SYNTHESIS,CHIRAL AZIRIDINES,GAMMA-LACTONES,PIPERIDINES,PRECURSORS,EPOXIDES,SCAFFOLD,POTENT,TRANSFORMATION},
  language     = {eng},
  number       = {14},
  pages        = {4945--4951},
  title        = {LiAlH4-Induced selective ring rearrangement of 2-(2-cyanoethyl)aziridines toward 2-(aminomethyl)pyrrolidines and 3-aminopiperidines as eligible heterocyclic building blocks},
  url          = {http://dx.doi.org/10.1002/chem.201504853},
  volume       = {22},
  year         = {2016},
}

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