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.
Document type :
Theses
Complete list of metadatas

Cited literature [904 references]  Display  Hide  Download

https://tel.archives-ouvertes.fr/tel-02390309
Contributor : Abes Star <>
Submitted on : Tuesday, December 3, 2019 - 3:26:03 AM
Last modification on : Wednesday, December 4, 2019 - 1:38:58 AM

File

JERHAOUI_Soufyan_2018_ED222.pd...
Version validated by the jury (STAR)

Identifiers

  • HAL Id : tel-02390309, version 1

Collections

Citation

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

Share

Metrics

Record views

123

Files downloads

7