title: Conformation-induced regioselective and divergent opening of epoxides by fluoride: facile access to hydroxylated fluoro-piperidines.
abstract: Utilizing molecular conformation as a controlling factor, epoxide-containing 2-aryl-piperidines can be ring-opened with the reagent combination of tetrabutylammonium fluoride (TBAF) and potassium bifluoride (KHF2) in a regioselective and divergent fashion. Four different types of hydroxylated fluoro-piperidines, valuable building blocks in drug development, were readily synthesized using this method. The basic nature of the reagent combination allowed a one-pot deprotection/ring opening process, which increased the efficacy of this transformation.
authors.affiliation: National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, China. huxiangg@iccas.ac.cn.
authors.forename: Nan
authors.initials: N
authors.lastname: Yan
authors.forename: Zheng
authors.initials: Z
authors.lastname: Fang
authors.forename: Qing-Quan
authors.initials: QQ
authors.lastname: Liu
authors.forename: Xiao-Hong
authors.initials: XH
authors.lastname: Guo
authors.forename: Xiang-Guo
authors.initials: XG
authors.lastname: Hu