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Agrandissement de cycle de pyrrolidines et de pipéridines : Synthèse d’alpha-fluoroalkyl-azépanes et azocanes

Abstract : The synthesis of medium sized heterocycles synthesis has always been challenging in organic chemistry. Moreover, in medicinal chemistry, nitrogen containing heterocycles are important as they are present in a variety of bioactive molecules. As the fluorine atom can improve the biological properties of a molecule, the development of new methods to access medium-size fluorinated heterocycles could be of interest. In this manuscript, we report an efficient method to accessα-fluoroalkyl-azepanes and azocanes by a ring-expansion. The key step of this method is the regioselective ring-opening of a bicyclic azétidinium intermediate, which can be achieved using a variety of nucleophiles.
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Guillaume Masson. Agrandissement de cycle de pyrrolidines et de pipéridines : Synthèse d’alpha-fluoroalkyl-azépanes et azocanes. Chimie organique. Université Paris sciences et lettres, 2019. Français. ⟨NNT : 2019PSLET041⟩. ⟨tel-03591986⟩

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