TY - JOUR
T1 - An Iridium-Catalyzed Reductive Approach to Nitrones from N-Hydroxyamides
AU - Katahara, Seiya
AU - Kobayashi, Shoichiro
AU - Fujita, Kanami
AU - Matsumoto, Tsutomu
AU - Sato, Takaaki
AU - Chida, Noritaka
N1 - Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/4/27
Y1 - 2016/4/27
N2 - An Ir-catalyzed reductive formation of functionalized nitrones from N-hydroxyamides was reported. The reaction took place through two types of iridium-catalyzed reactions including dehydrosilylation and hydrosilylation. The method showed high chemoselectivity in the presence of sensitive functional groups, such as methyl esters, and was successfully applied to the synthesis of cyclic and macrocyclic nitrones, which are known to be challenging compounds to access by conventional methods. 1H NMR studies strongly supported generation of an N-siloxyamide and an N,O-acetal as the actual intermediates.
AB - An Ir-catalyzed reductive formation of functionalized nitrones from N-hydroxyamides was reported. The reaction took place through two types of iridium-catalyzed reactions including dehydrosilylation and hydrosilylation. The method showed high chemoselectivity in the presence of sensitive functional groups, such as methyl esters, and was successfully applied to the synthesis of cyclic and macrocyclic nitrones, which are known to be challenging compounds to access by conventional methods. 1H NMR studies strongly supported generation of an N-siloxyamide and an N,O-acetal as the actual intermediates.
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U2 - 10.1021/jacs.6b02324
DO - 10.1021/jacs.6b02324
M3 - Article
AN - SCOPUS:84966440656
SN - 0002-7863
VL - 138
SP - 5246
EP - 5249
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 16
ER -