Skip to Main content Skip to Navigation
Theses

Cycloaddition [3+2] de cétènes avec des aziridines

Abstract : This thesis work focuses on a new type of [3+2] cycloaddition of ketenes with aziridines. Aziridines are good precursors of zwitterionic 1,3-aza-dipoles, by selective C-N bond cleavage catalyzed by Lewis acid. We have found that ketenes react with the 1,3-dipole generated by addition of lithium iodide to the aziridine, efficiently providing the gamma-lactams. This new cycloaddition could be extended to a one-pot simple transformation of imines to gamma-lactams. The synthesis is compatible with a wide range of aromatic imines and stable ketenes. Finally, a one-pot catalytic asymmetric synthesis of enantioenrichied gamma-lactams have been developed starting from olefins, involving an asymmetric nitrene aziridination.
Document type :
Theses
Complete list of metadatas

Cited literature [98 references]  Display  Hide  Download

https://tel.archives-ouvertes.fr/tel-01686116
Contributor : Abes Star :  Contact
Submitted on : Wednesday, January 17, 2018 - 9:05:08 AM
Last modification on : Friday, July 17, 2020 - 8:34:05 AM
Long-term archiving on: : Monday, May 7, 2018 - 1:32:54 PM

File

VICERIAT_2015_archivage.pdf
Version validated by the jury (STAR)

Identifiers

  • HAL Id : tel-01686116, version 1

Collections

Citation

Audrey Viceriat. Cycloaddition [3+2] de cétènes avec des aziridines. Chimie organique. Université Grenoble Alpes, 2015. Français. ⟨NNT : 2015GREAV049⟩. ⟨tel-01686116⟩

Share

Metrics

Record views

419

Files downloads

1678