TY - JOUR
T1 - Synthesis of enaminones by rhodium-catalyzed denitrogenative rearrangement of 1-(N -Sulfonyl-1,2,3-triazol-4-yl)alkanols
AU - Miura, Tomoya
AU - Funakoshi, Yuuta
AU - Morimoto, Masao
AU - Biyajima, Tsuneaki
AU - Murakami, Masahiro
PY - 2012/10/24
Y1 - 2012/10/24
N2 - Enaminones are synthesized by the rhodium(II)-catalyzed denitrogenative rearrangement reaction of 1-(N-sulfonyl-1,2,3-triazol-4-yl)alkanols, which are readily prepared from propargylic alcohols and N-sulfonyl azides. Intramolecular 1,2-hydride (or -alkyl) migration occurs with an intermediary α-imino rhodium(II) carbenoid species generated through denitrogenation of the 1,2,3-triazol-4-yl moiety. The resulting enaminones is converted into various heterocycles with replacement of the N-sulfonyl group.
AB - Enaminones are synthesized by the rhodium(II)-catalyzed denitrogenative rearrangement reaction of 1-(N-sulfonyl-1,2,3-triazol-4-yl)alkanols, which are readily prepared from propargylic alcohols and N-sulfonyl azides. Intramolecular 1,2-hydride (or -alkyl) migration occurs with an intermediary α-imino rhodium(II) carbenoid species generated through denitrogenation of the 1,2,3-triazol-4-yl moiety. The resulting enaminones is converted into various heterocycles with replacement of the N-sulfonyl group.
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U2 - 10.1021/ja308285r
DO - 10.1021/ja308285r
M3 - Article
C2 - 23043352
AN - SCOPUS:84867833006
VL - 134
SP - 17440
EP - 17443
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 42
ER -