Organocopper-Triggered Cyclisation of Conjugated Diene-ynes: Diastereo- and Enantioselective Synthesis of Indenes - Aix-Marseille Université Accéder directement au contenu
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2015

Organocopper-Triggered Cyclisation of Conjugated Diene-ynes: Diastereo- and Enantioselective Synthesis of Indenes

Tanzeel Arif
  • Fonction : Auteur
Cyril Borie
  • Fonction : Auteur
Aura Tintaru
  • Fonction : Auteur
Nicolas Vanthuyne
Michèle P. Bertrand
  • Fonction : Auteur
Malek Nechab

Résumé

Organocopper reagents react with readily available chiral conjugated diene-ynes to give indene derivatives bearing two stereogenic centres. The investigation of this original reaction in optically pure series demonstrates that a double transfer of chirality is operating. A stereocontrolled cascade involving S(N)2' followed by carbocupration and conjugate addition reactions accounts for the total recovery of the initial chirality. The scope and limitations of the reaction were investigated. The high diastereofacial discrimination in the cyclisation step allowed the construction of the quaternary stereocentre with excellent dr and ee, with the opposite configuration depending on the E- or Z-configuration of the alkene in the starting material. Post-functionalisation of indenes allowed the synthesis of indanyl derivatives containing four contiguous stereocentres.

Domaines

Chimie organique

Dates et versions

hal-01406322 , version 1 (01-12-2016)

Identifiants

Citer

Tanzeel Arif, Cyril Borie, Aura Tintaru, Jean-Valère Naubron, Nicolas Vanthuyne, et al.. Organocopper-Triggered Cyclisation of Conjugated Diene-ynes: Diastereo- and Enantioselective Synthesis of Indenes. Advanced Synthesis and Catalysis, 2015, 357 (16-17), pp.3611 - 3616. ⟨10.1002/adsc.201500556⟩. ⟨hal-01406322⟩
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