Access to Atropisomerically Enriched Biaryls by the Coupling of Aryllithiums with Arynes under Control by Homochiral Oxazolines
| Pas de texte intégral | |
|---|---|
| Auteurs |
Boubacar Yalcouye Anaïs Brehier David Augros Armen Panossian Sabine Choppin Matthieu Chessé Francoise Colobert-leuenberger Frederic Leroux |
| Unité de recherche du site |
Laboratoire de Chimie Moléculaire - LCM - UMR7509 |
| Langue |
en |
| Volume |
2016 |
| Numéro |
4 |
| Page de début |
725 |
| Page de fin |
732 |
| Date de première publication |
2016 |
| ISSN |
1099-0690 |
| Titre de la source (revue, livre…) |
European Journal of Organic Chemistry |
| Résumé |
We report the preparation of axially stereoenriched biphenyls by the coupling of in situ generated aryllithiums and arynes using chiral oxazoline auxiliaries. The design of the aryne precursors, the choice of oxazoline and the reaction conditions Show moreWe report the preparation of axially stereoenriched biphenyls by the coupling of in situ generated aryllithiums and arynes using chiral oxazoline auxiliaries. The design of the aryne precursors, the choice of oxazoline and the reaction conditions were key to accessing the desired, highly substituted, atropisomerically enriched biarylic products. In one case, the two atropo-diastereomers could be obtained in isomerically pure form by column chromatographic separation and their absolute configurations established by X-ray crystallography. The stereoselectivity of the reaction seems to be governed by subtle parameters. Show less |
| DOI | 10.1002/ejoc.201501503 |
| Éditeur |
Wiley-VCH Verlag |
| Éditeur |
WILEY-VCH Verlag |
| URL éditeur |
http://dx.doi.org/10.1002/ejoc.201501503 |
| Type de publication |
journal article |
| Type de publication |
ACL |
| Domaine |
Chimie/Chimie organique |
| Fonction |
ctb |
| Audience |
Non spécifiée |
| Envoyer vers HAL |
5 |
| URL | https://univoak.eu/islandora/object/islandora:54696 |