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Synthesis of Novel Cyclic Nitrones withgem-Difluoroalkyl Side Chains Through Cascade Reactions

Authors
  • Soulieman, Ali
  • Ibrahim, Rima
  • Barakat, Zeinab
  • Gouault, Nicolas
  • Roisnel, Thierry
  • Boustie, Joël
  • Grée, René
  • Hachem, Ali
Publication Date
Jan 01, 2020
Identifiers
DOI: 10.1002/ejoc.202000972
OAI: oai:HAL:hal-02957740v1
Source
HAL-Descartes
Keywords
Language
English
License
Unknown
External links

Abstract

New five-membered cyclic nitrones withgem-difluoroalkyl groups in gamma-position have been prepared by a 3-step sequence starting from propargylic alcohols. This domino process involves a base-mediated isomerization reaction to enones, which are trapped in situ by nitroalkane anions. In a final step, starting from these key precursors, a reduction-cyclization process affords the target molecules. Mono- and bicyclic nitrones have been prepared by this route which allows, as well, the synthesis of nitrones with functional groups in terminal position of the side chain.

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