Inorganic-Base-Mediated Hydroamination of Alkenyl Oximes for the Synthesis of Cyclic Nitrones

摘要

A method based on hydroamination mediated by inorganic base was developed for the synthesis of cyclic Snitrones from alkenyl oximes. DFTcalculations 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.