Organocopper triggered cyclization of conjugated dienynes via tandem S N 2′/Alder-ene reaction - Archive ouverte HAL Access content directly
Journal Articles Organic Chemistry Frontiers Year : 2018

Organocopper triggered cyclization of conjugated dienynes via tandem S N 2′/Alder-ene reaction

(1) , (1) , (2) , (2) , (1) , (1) , (1)
1
2

Abstract

Propargylic carbonates were converted to indenes through a S N 2'/Alder-ene cascade triggered by organocopper reagents. The reaction tolerates different organocopper species generated either from organolithiums or Grignard reagents. A catalytic version of this strategy could be devised using either copper or iron catalysts. Attempts to transfer chirality from an enantioenriched substrate revealed a moderate chirality conversion because of a low discrimination between the two faces of the internal olefinic partner with these typical substrates. The theoretical investigation supports a concerted closed-shell mechanism and highlights the influence of the substituents on the activation parameters and on the synchronicity of C-H bond breaking and CC bond forming during the Alder-ene step.
Fichier principal
Vignette du fichier
2018-MN.pdf (375.59 Ko) Télécharger le fichier
Origin : Files produced by the author(s)
Loading...

Dates and versions

hal-02053476 , version 1 (07-04-2019)

Identifiers

Cite

Tanzeel Arif, Cyril Borie, Marion Jean, Nicolas Vanthuyne, Michèle Bertrand, et al.. Organocopper triggered cyclization of conjugated dienynes via tandem S N 2′/Alder-ene reaction. Organic Chemistry Frontiers, 2018, 5 (5), pp.769-776. ⟨10.1039/c7qo00288b⟩. ⟨hal-02053476⟩
15 View
123 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More