title: Inorganic-base-mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones.
abstract: A method based on hydroamination mediated by inorganic base was developed for the synthesis of cyclic nitrones from alkenyl oximes. DFT calculations of the reaction pathway suggested that this hydroamination could proceed through an unprecedented nucleophilic amination of the unactivated alkene by the oxime nitrogen atom. The transition state of this reaction is stabilized by an ionic interaction between a metal cation such as K(+) and the oxime oxygen and negatively charged alkene moiety.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore).
authors.forename: Xingao
authors.initials: X
authors.lastname: Peng
authors.forename: Benny Meng Kiat
authors.initials: BM
authors.lastname: Tong
authors.forename: Hajime
authors.initials: H
authors.lastname: Hirao
authors.forename: Shunsuke
authors.initials: S
authors.lastname: Chiba
keywords: 1,3-dipoles; density functional calculations; hydroamination; nitrones; oximes