Premium
Inorganic‐Base‐Mediated Hydroamination of Alkenyl Oximes for the Synthesis of Cyclic Nitrones
Author(s) -
Peng Xingao,
Tong Benny Meng Kiat,
Hirao Hajime,
Chiba Shunsuke
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201308617
Subject(s) - hydroamination , amination , oxime , chemistry , alkene , nucleophile , moiety , base (topology) , nitrogen atom , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , alkyl , mathematics , mathematical analysis
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.