Accéder directement au contenu Accéder directement à la navigation
Article dans une revue

Zirconocene-Mediated Selective C–C Bond Cleavage of Strained Carbocycles: Scope and Mechanism

Abstract : Several approaches using organozirconocene species for the remote cleavage of strained three-membered ring carbocycles are described. ω-Ene polysubstituted cyclopropanes, alkylidenecyclopropanes, ω-ene spiro[2.2]pentanes, and ω-ene cyclopropyl methyl ethers were successfully transformed into stereodefined organometallic intermediates, allowing an easy access to highly stereoenriched acyclic scaffolds in good yields and, in most cases, excellent selectivities. DFT calculations and isotopic labeling experiments were performed to delineate the origin of the obtained chemo- and stereoselectivities, demonstrating the importance of microreversibility.
Type de document :
Article dans une revue
Domaine :
Liste complète des métadonnées

https://hal.umontpellier.fr/hal-01767301
Contributeur : Anthony Herrada Connectez-vous pour contacter le contributeur
Soumis le : lundi 16 avril 2018 - 10:03:56
Dernière modification le : lundi 11 octobre 2021 - 13:23:19

Identifiants

Citation

Jeffrey Bruffaerts, Alexandre Vasseur, Sukhdev Singh, Ahmad Masarwa, Dorian Didier, et al.. Zirconocene-Mediated Selective C–C Bond Cleavage of Strained Carbocycles: Scope and Mechanism. Journal of Organic Chemistry, American Chemical Society, 2018, 83 (7), pp.3497 - 3515. ⟨10.1021/acs.joc.7b03115⟩. ⟨hal-01767301⟩

Partager

Métriques

Consultations de la notice

173