Résumé
We report efficient stereoselective and high yielding syntheses of each of the four enantiomers of phenylcyclopentanes bearing a quaternary center and a E-propenyl chain on the adjacent carbon that involves intramolecular allylic substitution reactions. In complement to its synthetic value, this process models the SN' reaction and allows prediction of its stereochemical outcome.
| langue originale | Anglais |
|---|---|
| Pages (de - à) | 308-333 |
| Nombre de pages | 26 |
| journal | ARKIVOC |
| Volume | 2018 |
| Numéro de publication | 5 |
| Les DOIs | |
| Etat de la publication | Publié - 7 juil. 2018 |
Financement
The work presented in this paper was initiated in 2004 by Francois Adam (FA) assistant and enrolled as a PhD student, then carried out in 2007 by Hélène Vanderhauwaer (HV) a PhD student supported by the FRIA Belgium (Laboratoire de Chimie Organique de Synthèse, Facultés N.D de la Paix, Namur). Both of them decided to stop their work for personal reasons. Their fragmentary results have been consigned in their progress reports (a) January-July 2005 and (b) January-July 2007 respectively. All the results reported here, except those involving the transformation of 4cE to 11 and 4a (FA, research report 2005) have been carried out by Dr Adrian Kremer in the laboratory of Prof. D. Bonifazi. The Authors thanks Prof. Davide Bonifazi for strongly supporting this work and Prof. Guillaume Berionni for helpful discussions.
Empreinte digitale
Examiner les sujets de recherche de « Formalizing the mechanism of the allylic substitution reaction (SN'): Application to the highly enantio- and diastereo-selective syntheses of 1-phenyl-2-vinylcyclopentanes ». Ensemble, ils forment une empreinte digitale unique.Équipement
-
Physico-chimie et caractérisation (PC2)
Wouters, J. (!!Manager), Aprile, C. (!!Manager) & Fusaro, L. (!!Manager)
Plateforme technologique Caracterisation physico-chimiquesEquipement/installations: Plateforme technolgique
Ensembles de données
-
CCDC 923100: Experimental Crystal Structure Determination
Krief, A. (Contributeur), Wouters, J. (Contributeur), Norberg, B. (Contributeur) & Kremer, A. (Contributeur), University of Namur, 7 juil. 2018
DOI: 10.5517/ccdc.csd.cczzkfx, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cczzkfx&sid=DataCite
Ensemble de données
-
CCDC 923101: Experimental Crystal Structure Determination
Krief, A. (Contributeur), Wouters, J. (Contributeur), Norberg, B. (Contributeur) & Kremer, A. (Contributeur), University of Namur, 7 juil. 2018
DOI: 10.5517/ccdc.csd.cczzkgy, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cczzkgy&sid=DataCite
Ensemble de données
-
CCDC 923102: Experimental Crystal Structure Determination
Krief, A. (Contributeur), Wouters, J. (Contributeur), Norberg, B. (Contributeur) & Kremer, A. (Contributeur), University of Namur, 7 juil. 2018
DOI: 10.5517/ccdc.csd.cczzkhz, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cczzkhz&sid=DataCite
Ensemble de données