Efficient intermolecular 3+2 trapping of the Nazarov intermediate with vinyl sulfides |
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Authors: | Bahja Mahmoud |
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Institution: | Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB, Canada T6G 2G2 |
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Abstract: | Cross-conjugated 1,4-pentadien-3-ones undergo electrocyclization to 2-oxidocyclopentenyl cations upon treatment with BF3·OEt2. When these reactions are carried out in the presence of electron-rich vinyl sulfides, nucleophilic trapping followed by ring-closure furnishes bridged bicyclic products that can be viewed as formal 3+2 cycloadducts. This process results in three new carbon-carbon bonds and establishes up to five new stereocenters. |
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