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Couplage croisé d’éthers d’énol méthyliques par activation de liaisons C(sp2)-OCH3 catalysée par le nickel et Synthèse d’amines α-trifluorométhylées acycliques optiquement activespar réarrangement de β-aminoalcools α-trifluorométhylés

Abstract : In organic chemistry, the development of robust and sustainable synthetic methods has always been a challenge. Moreover, in medicinal chemistry, the development of fluorinated building blocks synthetic methods with high value is important to access bioactive compounds. In this manuscript, we report efficient and easy to carry methods for the formation of carbon-carbon bonds catalyzed by nickel and the formation of carbon-heteroatom bonds by a rearrangement of α-trifluoromethyl-β aminoalcools.We demonstrated that it is possible to perform a cross-coupling reaction of an alkenyl methy ether with a Grignard reagent using a simple catalytic system based on Ni(OAc)2/(O)PPh3 under mild conditions (40°C) via the insertion of nickel into C-OMe bond. This method has been applied to the synthesis of an antitumoral agent, DMU-212.The synthesis of enantioenriched linear α-trifluoromethylamine derivatives is reported consisting in a rearrangement of α-trifluoromethyl-β aminoalcool based on an established strategy in our group via an aziridinium intermediate. We have shown that the synthesized compounds can be involved in post-functionalization reactions.
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Zeïna Neouchy. Couplage croisé d’éthers d’énol méthyliques par activation de liaisons C(sp2)-OCH3 catalysée par le nickel et Synthèse d’amines α-trifluorométhylées acycliques optiquement activespar réarrangement de β-aminoalcools α-trifluorométhylés. Chimie organique. Université Paris sciences et lettres, 2018. Français. ⟨NNT : 2018PSLET016⟩. ⟨tel-03456308⟩

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