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

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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Submitted on : Thursday, October 8, 2020 - 3:13:19 PM
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Ali Soulieman, Rima Ibrahim, Zeinab Barakat, Nicolas Gouault, Thierry Roisnel, et al.. Synthesis of Novel Cyclic Nitrones withgem-Difluoroalkyl Side Chains Through Cascade Reactions. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2020, 2020 (35), pp.5741-5751. ⟨10.1002/ejoc.202000972⟩. ⟨hal-02957740⟩

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