Journal articles
Organocopper triggered cyclization of conjugated dienynes via tandem S N 2′/Alder-ene reaction
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.
Cited literature [30 references]
https://hal-amu.archives-ouvertes.fr/hal-02053476
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Submitted on : Sunday, April 7, 2019 - 6:20:39 AM
Last modification on : Tuesday, January 4, 2022 - 5:06:54 AM
Contributor : Didier Siri Connect in order to contact the contributor
Submitted on : Sunday, April 7, 2019 - 6:20:39 AM
Last modification on : Tuesday, January 4, 2022 - 5:06:54 AM
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