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

文献情報

出版日 2017-11-24

DOI 10.1039/C7QO00288B

インパクトファクター 5.281

著者

Tanzeel Arif, Cyril Borie, Marion Jean, Nicolas Vanthuyne, Michèle P. Bertrand, Didier Siri, Malek Nechab

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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

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