Watcharaporn ThaharnDarunee SoorukramChutima KuhakarnVichai ReutrakulManat PohmakotrRajabhat UniversityMahidol University2019-08-232019-08-232018-01-05Journal of Organic Chemistry. Vol.83, No.1 (2018), 388-40215206904002232632-s2.0-85042004179https://repository.li.mahidol.ac.th/handle/20.500.14594/45516© 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.Mahidol UniversityChemistryArticleSCOPUS10.1021/acs.joc.7b02777