Asymmetric palladium (0)-catalyzed C(sp³)-H arylation and natural product synthesis

Melot, Romain. Asymmetric palladium (0)-catalyzed C(sp³)-H arylation and natural product synthesis. 2019, Doctoral Thesis, University of Basel, Faculty of Science.


Official URL: http://edoc.unibas.ch/diss/DissB_13480

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Over the last decades, C(sp3)-H activation has emerged as a powerful tool for building structural complexity in a step-economical manner. In this context, our group developed diverse methodologies and applied them to the synthesis of natural products, bioactive molecules and valuable building blocks.
More recently, our group was attracted, as others, by the development of asymmetric versions of such reactions. In this regard, the synthesis of enantioenriched indanes through asymmetric palladium-catalyzed C(sp3)-H arylation was described using a chiral binepine ligand for chiral induction. This work motivated us to develop other asymmetric reactions and apply them to the synthesis of interesting compounds.
In this optic, we first investigated the use of a chiral anion as an alternative to the classic approach using chiral NHC or phosphorylated ligands. This led to the development of a new methodology for the synthesis of enantioenriched indolines.
We then elaborated a divergent asymmetric synthesis of three (nor)illudalanes sesquiterpenes using C(sp3)-H arylation as the key step, which demonstrates the potential of such transformations to access chiral natural products.
Finally, we are actually developing a new methodology for the asymmetric C(sp3)-H arylation of unactivated methylene positions to prepare valuable indanes related to potential natural product targets.
Advisors:Baudoin, Olivier and Cramer, Nicolai
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische Chemie (Baudoin)
UniBasel Contributors:Melot, Romain and Baudoin, Olivier
Item Type:Thesis
Thesis Subtype:Doctoral Thesis
Thesis no:13480
Thesis status:Complete
Number of Pages:1 Online-Ressource (507 Seiten)
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edoc DOI:
Last Modified:01 Jan 2021 02:30
Deposited On:18 Mar 2020 10:10

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