Jump to main content
Jump to site search


Organocopper triggered cyclization of conjugated dienynes via tandem SN2′/Alder-ene reaction

Author affiliations

Abstract

Propargylic carbonates were converted to indenes through a SN2′/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 C–C bond forming during the Alder-ene step.

Graphical abstract: Organocopper triggered cyclization of conjugated dienynes via tandem SN2′/Alder-ene reaction

Back to tab navigation

Supplementary files

Publication details

The article was received on 12 Apr 2017, accepted on 15 Nov 2017 and first published on 24 Nov 2017


Article type: Research Article
DOI: 10.1039/C7QO00288B
Citation: Org. Chem. Front., 2018, Advance Article
  •   Request permissions

    Organocopper triggered cyclization of conjugated dienynes via tandem SN2′/Alder-ene reaction

    T. Arif, C. Borie, M. Jean, N. Vanthuyne, M. P. Bertrand, D. Siri and M. Nechab, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00288B

Search articles by author

Spotlight

Advertisements