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Sulfoxydes : novel strategy for the asymmetric C(sp3)-H activation

Abstract : Over the decades, non-activated C-H bonds have been considered as dormant functionalities, hardly exploitable in the context of multistep synthesis of complex scaffolds. The main challenge is to select one C-H bond among all contained in one molecule. To answer to this problem bicoordinating directing groups allowing directed C(sp3)-H activation have been developed. Following the work of Daugulis and Babu, we developed our own chiral bicoordinating directing group, (S)-2-(p-tolylsulfinyl)aniline. This chiral auxiliary allowed us to realise various diastereoselective transformations on aliphatic chains such as arylation, olefination oracetoxylation. We also used it to develop a brand-new methodology for the total synthesis ofcyclopropane-bearing natural products. Moreover we developed a new chiral sulfinyl ligand, N-((S)-1-(4-(tert-butyl)phenyl)-2-((R)-p-tolylsulfinyl)ethyl)acetamide, that has been used for the enantioselective arylation and alkynylation of cycloalkanes.
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Submitted on : Tuesday, December 3, 2019 - 3:26:03 AM
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  • HAL Id : tel-02390309, version 1



Soufyan Jerhaoui. Sulfoxydes : novel strategy for the asymmetric C(sp3)-H activation. Organic chemistry. Université de Strasbourg, 2018. English. ⟨NNT : 2018STRAF025⟩. ⟨tel-02390309⟩



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