title: Cycloaddition of Fluorenone N-Aryl Nitrones with Methylenecyclopropanes and Sequential 1,3-Rearrangement: An Entry to Synthesis of Spirofluorenylpiperidin-4-ones.
abstract: A facile synthesis of various spirofluorenylpiperidin-4-ones has been achieved in good yields from fluorenone N-aryl nitrones and methylenecyclopropanes. This method involved an initial cycloaddition to form a 5-spirocyclopropane-isoxazoline, which underwent a highly selective 1,3-rearrangement to give the desired product. The stereochemistry of the spirofluorenylpiperidin-4-one could be controlled by the cycloaddition and sequential rearrangement strategy. Furthermore, the spirofluorenylpiperidin-4-ones could be not only prepared in one-pot procedure but also converted to useful scaffolds by reduction or oxidation conditions.
authors.affiliation: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China; School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, China.
authors.forename: Xiao-Pan
authors.initials: XP
authors.lastname: Ma
authors.affiliation: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China; School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, China.
authors.forename: Jie-Feng
authors.initials: JF
authors.lastname: Zhu
authors.affiliation: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China; School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, China.
authors.forename: Si-Yi
authors.initials: SY
authors.lastname: Wu
authors.affiliation: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China; School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, China.
authors.forename: Chun-Hua
authors.initials: CH
authors.lastname: Chen
authors.affiliation: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China; School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, China.
authors.forename: Ning
authors.initials: N
authors.lastname: Zou
authors.affiliation: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China; School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, China.
authors.forename: Cui
authors.initials: C
authors.lastname: Liang
authors.affiliation: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China; School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, China.
authors.forename: Gui-Fa
authors.initials: GF
authors.lastname: Su
authors.affiliation: State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Science and Technology of China; School of Chemistry & Pharmaceutical Sciences, Guangxi Normal University , 15 Yu Cai Road, Guilin 541004, China.
authors.forename: Dong-Liang
authors.identifier: 0000-0002-4005-2249
authors.initials: DL
authors.lastname: Mo