Chemistry Program, Faculty of Education, Chiangrai Rajabhat University , Mueang Chiang Rai, Chiang Rai 57100, Thailand.
Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University , Rama VI Road, Bangkok 10400, Thailand.
J Org Chem. 2018 Jan 5;83(1):388-402. doi: 10.1021/acs.joc.7b02777. Epub 2017 Dec 21.
A synthesis of symmetrical gem-difluoromethylenated angular triquinanes is described. The synthetic strategy involved sequential fluoride-catalyzed nucleophilic addition of PhSCFSiMe (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 C-symmetric gem-difluoromethylenated angular triquinanes 6 in good yields with high stereoselectivity.
描述了一种对称的全氟亚甲基角三嗪的合成方法。该合成策略包括顺序氟催化亲核加成 PhSCFSiMe（1）到 2,2-二烯丙基化或 2,2-二炔丙基化茚-1,3-二酮 2，然后对得到的加成物 3进行立体选择性自由基环化，得到作为立体异构体混合物的环化全氟亚甲基二嗪 4。重复添加 1 到 4 并进行环化反应，以高产率和高立体选择性得到所需的 C-对称全氟亚甲基角三嗪 6。
