TY - JOUR
T1 - Inorganic-base-mediated hydroamination of alkenyl oximes for the synthesis of cyclic nitrones
AU - Peng, Xingao
AU - Tong, Benny Meng Kiat
AU - Hirao, Hajime
AU - Chiba, Shunsuke
PY - 2014/2/10
Y1 - 2014/2/10
N2 - 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. Basic ring building: A method for the synthesis of cyclic nitrones by using alkenyl oximes was developed based on hydroamination mediated by an inorganic base. DFT calculations for the reaction pathway suggested that this hydroamination could proceed through nucleophilic amination of the unactivated alkene by the oxime nitrogen atom, with the transition state stabilized by ionic interaction with a metal cation such as K+. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
AB - 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. Basic ring building: A method for the synthesis of cyclic nitrones by using alkenyl oximes was developed based on hydroamination mediated by an inorganic base. DFT calculations for the reaction pathway suggested that this hydroamination could proceed through nucleophilic amination of the unactivated alkene by the oxime nitrogen atom, with the transition state stabilized by ionic interaction with a metal cation such as K+. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
KW - 1,3-dipoles
KW - density functional calculations
KW - hydroamination
KW - nitrones
KW - oximes
UR - http://www.scopus.com/inward/record.url?scp=84893597055&partnerID=8YFLogxK
UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-84893597055&origin=recordpage
U2 - 10.1002/anie.201308617
DO - 10.1002/anie.201308617
M3 - RGC 21 - Publication in refereed journal
SN - 1433-7851
VL - 53
SP - 1959
EP - 1962
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 7
ER -