Skip to Main content Skip to Navigation
Theses

Agrandissement de cycle de propinols optiquement actifs - Application à la synthèse de composés biologiquement actifs

Abstract : Prolinols can be transformed into 3-hydroxypiperidines by a stereoselective ring expansion induced by trifluoroacetic anhydride. This rearrangement proceed via an aziridinium intermediate. This reaction was used in the formal synthesis of Ro 67-8867 from α-methylbenzylamine, a zinc- enolate cyclization and the ring expansion were used as key-steps. Two formal syntheses of (-)-swainsonine have also been achieved from L-proline by using a diastereoselective addition of an organometallic species onto a prolinal, a ring-closing metathesis, a diastereoselective dihydroxylation and the ring expansion of prolinols. By analogy with the ring expansion induced by trifluoroacetic anhydride, the ring enlargement of prolinols in the presence of DAST was envisaged. In general, a mixture of 3-fluoropiperidines and fluorométhylpyrrolidines is obtained. When prolinols were substituted by a bulkygroup at C4, C2 or on the nitrogen, a selective ring expansion was observed.
Document type :
Theses
Complete list of metadatas

Cited literature [39 references]  Display  Hide  Download

https://pastel.archives-ouvertes.fr/pastel-00002248
Contributor : Ecole Espci Paristech <>
Submitted on : Friday, April 20, 2007 - 8:00:00 AM
Last modification on : Wednesday, October 14, 2020 - 3:42:57 AM
Long-term archiving on: : Thursday, September 30, 2010 - 7:58:11 PM

Identifiers

  • HAL Id : pastel-00002248, version 1

Citation

Ingrid Déchamps. Agrandissement de cycle de propinols optiquement actifs - Application à la synthèse de composés biologiquement actifs. Chimie. Université Pierre et Marie Curie - Paris VI, 2007. Français. ⟨pastel-00002248⟩

Share

Metrics

Record views

393

Files downloads

1121