fr
Article scientifique
Anglais

Copper-catalyzed asymmetric allylic alkylation of racemic cyclic substrates: application of dynamic kinetic asymmetric transformation (DYKAT)

Publié dansAdvanced synthesis & catalysis, vol. 352, no. 2-3, p. 447-457
Date de publication2010
Résumé

The copper-catalyzed asymmetric allylic alkylation (AAA) is of great interest in organic synthesis. This reaction was extensively studied using a broad range of substrates, ligands and organometallic reagents. However, the use of racemic substrates was still limited. Although some processes of kinetic resolution are reported in the literature, no examples of quantitative deracemization are described as is the case for the Pd-catalyzed allylic alkylation. We present here a full account of our investigations through the development of the first example of such a process in copper-catalyzed AAA. High enantioselectivities (up to 99% ee), scope of the reaction and mechanistic considerations are reported herein.

Mots-clés
  • Allylic alkylation
  • Allylic compounds
  • Asymmetric catalysis
  • Copper
  • Nucleophilic substitution
Citation (format ISO)
LANGLOIS, Jean-Baptiste, ALEXAKIS, Alexandre. Copper-catalyzed asymmetric allylic alkylation of racemic cyclic substrates: application of dynamic kinetic asymmetric transformation (DYKAT). In: Advanced synthesis & catalysis, 2010, vol. 352, n° 2-3, p. 447–457. doi: 10.1002/adsc.200900790
Fichiers principaux (1)
Article (Published version)
accessLevelRestricted
Identifiants
ISSN du journal1615-4150
604vues
0téléchargements

Informations techniques

Création22.02.2010 17:32:00
Première validation22.02.2010 17:32:00
Heure de mise à jour14.03.2023 15:24:20
Changement de statut14.03.2023 15:24:20
Dernière indexation15.01.2024 19:34:10
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack