Organocopper triggered cyclization of conjugated dienynes via tandem SN2′/Alder-ene reaction. Issue 5 (24th November 2017)

• Record Type: Journal Article
• Authors: Arif, Tanzeel; Borie, Cyril; Jean, Marion; Vanthuyne, Nicolas; Bertrand, Michèle P.; Siri, Didier; Nechab, Malek
• Is Part Of: Organic chemistry frontiers. Volume 5:Issue 5(2018)
• Page Start: 769
• Page End: 776
• Publication Date: 2017-11-24
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c7qo00288b
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Propargylic carbonates were converted to indenes through a SN 2′/Alder-ene cascade triggered by organocopper reagents. Abstract : Propargylic carbonates were converted to indenes through a SN 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 C–C bond forming during the Alder-ene step.