Publication: Synthesis of C<inf>2</inf>-Symmetric gem-Difluoromethylenated Angular Triquinanes
Issued Date
2018-01-05
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ISSN
15206904
00223263
00223263
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2-s2.0-85042004179
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Mahidol University
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SCOPUS
Bibliographic Citation
Journal of Organic Chemistry. Vol.83, No.1 (2018), 388-402
Suggested Citation
Watcharaporn Thaharn, Darunee Soorukram, Chutima Kuhakarn, Vichai Reutrakul, Manat Pohmakotr Synthesis of C<inf>2</inf>-Symmetric gem-Difluoromethylenated Angular Triquinanes. Journal of Organic Chemistry. Vol.83, No.1 (2018), 388-402. doi:10.1021/acs.joc.7b02777 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/45516
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Title
Synthesis of C<inf>2</inf>-Symmetric gem-Difluoromethylenated Angular Triquinanes
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Abstract
© 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.