Synthesis of C<inf>2</inf>-Symmetric gem-Difluoromethylenated Angular Triquinanes
© 2017 American Chemical Society. A synthesis of symmetrical gem-difluoromethylenated angular triquinanes is described. The synthetic strategy involved sequential fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 (1) to 2,2-diallylated or 2,2-dipropargylated indane-1,3-diones 2 followed by ste...
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| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | Article |
| Published: |
2019
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| Subjects: | |
| Online Access: | https://repository.li.mahidol.ac.th/handle/123456789/45516 |
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| Institution: | Mahidol University |
| Summary: | © 2017 American Chemical Society. A synthesis of symmetrical gem-difluoromethylenated angular triquinanes is described. The synthetic strategy involved sequential fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 (1) to 2,2-diallylated or 2,2-dipropargylated indane-1,3-diones 2 followed by stereoselective radical cyclization of the resulting adducts 3 to provide the cyclized gem-difluoromethylenated diquinanes 4 as a mixture of stereoisomers. Repeated addition of 1 to 4 followed by cyclization resulted in the stereoselective synthesis of the desired C2-symmetric gem-difluoromethylenated angular triquinanes 6 in good yields with high stereoselectivity. |
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