Synthesis of gem -difluoromethylenated polycyclic cage compounds
© 2015 American Chemical Society. The synthesis of gem-difluoromethylenated polycyclic cage compounds, utilizing PhSCF2SiMe3 as a gem-difluoromethylene building block, is described. The fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 to both maleic anhydride-cyclopentadiene and maleic anhydr...
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| Main Authors: | , , , , , , , |
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| 格式: | Article |
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2018
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| 在線閱讀: | https://repository.li.mahidol.ac.th/handle/123456789/35758 |
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| 機構: | Mahidol University |
| 總結: | © 2015 American Chemical Society. The synthesis of gem-difluoromethylenated polycyclic cage compounds, utilizing PhSCF2SiMe3 as a gem-difluoromethylene building block, is described. The fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 to both maleic anhydride-cyclopentadiene and maleic anhydride-cyclohexadiene adducts was accomplished with high stereoselectivity to provide the corresponding adducts that were treated with Grignard reagents, followed by acid-catalyzed lactonization to afford the corresponding γ-butyrolactones, each as a single isomer. These γ-butyrolactones underwent intramolecular radical cyclization to give the corresponding tetracyclic cage γ-butyrolactones, which were employed as precursors for the synthesis of gem-difluoromethylenated tetracyclic cage lactols or tetracyclic cage furans, upon treatment with Grignard reagents. |
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