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Feraldi-Xypolia A, Gomez Pardo D, Cossy J. Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines. Chemistry. 2015;21(37):12876-80doi: 10.1002/chem.201502084.
Feraldi-Xypolia, A., Gomez Pardo, D., & Cossy, J. (2015). Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines. Chemistry (Weinheim an der Bergstrasse, Germany), 21(37), 12876-80. https://doi.org/10.1002/chem.201502084
Feraldi-Xypolia, Alexandra, et al. "Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,37 (2015): 12876-80. doi: https://doi.org/10.1002/chem.201502084
Feraldi-Xypolia A, Gomez Pardo D, Cossy J. Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines. Chemistry. 2015 Sep 07;21(37):12876-80. doi: 10.1002/chem.201502084. Epub 2015 Jul 23. PMID: 26218227.
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Chemistry. 2015 Sep 07;21(37):12876-80. doi: 10.1002/chem.201502084. Epub 2015 Jul 23.

Ring Contraction of 3-Hydroxy-3-(trifluoromethyl)piperidines: Synthesis of 2-Substituted 2-(Trifluoromethyl)pyrrolidines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Alexandra Feraldi-Xypolia, Domingo Gomez Pardo, Janine Cossy

Affiliations

  1. Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), UMR 8231 ESPCI ParisTech/CNRS/PSL Research University, 10 rue Vauquelin, 75231-Paris Cedex 05 (France).
  2. Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), UMR 8231 ESPCI ParisTech/CNRS/PSL Research University, 10 rue Vauquelin, 75231-Paris Cedex 05 (France). [email protected].
  3. Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation (CBI), UMR 8231 ESPCI ParisTech/CNRS/PSL Research University, 10 rue Vauquelin, 75231-Paris Cedex 05 (France). [email protected].

PMID: 26218227 DOI: 10.1002/chem.201502084

Abstract

A ring contraction of 3-hydroxy-3-(trifluoromethyl)piperidines was achieved via an aziridinium intermediate. This contraction facilitates the synthesis of a series of 2-substituted 2-(trifluoromethyl)pyrrolidines incorporating a quaternary center at the C2 position.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: aziridines; heterocycles; reactive intermediates; ring contraction; synthetic methods

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