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palladium-catalyzed asymmetric allylic alkylation : control of all-carbon quaternary centers in nitrogen-containing heterocycles

Abstract : The development of new synthetic tools allowing to create quaternary stereogenic centers remains an important challenge in synthetic organic chemistry. In this context, the palladium-catalyzed asymmetric allylic alkylation has become a particularly effective tool. The first chapter of this thesis is focused on the application of this key reaction to succinimide type compounds. This convergent method has allowed us to access a number of succinimide derivatives bearing a quaternary stereogenic center in high yields and excellent enantioselectivities. Moreover, in order to demonstrate the synthetic utility of the method, the resulting alpha-quaternary succinimides were converted to various useful building block including pyrrolidines and spirocyclic frameworks. The second chapter is focused on the application of the palladium-catalyzed asymmetric allylic alkylation to alpha,gamma-disubstituted 2-siloxypyrroles in order to access gamma-lactams bearing an alpha-quaternary stereogenic center in high yields and enantioselectivities. The latter were eventually converted to the corresponding pyrrolidines and pipéridinesKeywords: asymmetric catalysis, allylic alkylation, palladium, succinimides, lactams, all-carbon quaternary stereogenic centers
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Tao Song. palladium-catalyzed asymmetric allylic alkylation : control of all-carbon quaternary centers in nitrogen-containing heterocycles. Organic chemistry. Université Paris sciences et lettres, 2018. English. ⟨NNT : 2018PSLET012⟩. ⟨tel-02496962⟩

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