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Synthesis of Enaminones by Rhodium-Catalyzed Denitrogenative Rearrangement of 1‑(<i>N</i>‑Sulfonyl-1,2,3-triazol-4-yl)alkanols

By Tomoya Miura (1600264), Yuuta Funakoshi (1600273), Masao Morimoto (1928023), Tsuneaki Biyajima (1939186) and Masahiro Murakami (8477)


Enaminones are synthesized by the rhodium­(II)-catalyzed denitrogenative rearrangement reaction of 1-(<i>N</i>-sulfonyl-1,2,3-triazol-4-yl)­alkanols, which are readily prepared from propargylic alcohols and <i>N</i>-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 <i>N</i>-sulfonyl group

Topics: Genetics, Molecular Biology, Evolutionary Biology, Ecology, Mental Health, Mathematical Sciences not elsewhere classified, propargylic alcohols, carbenoid, hydride, migration, Enaminone, intermediary, Denitrogenative, azide, imino, denitrogenation, species, rhodium, Synthesi, heterocycle, enaminone, Rearrangement, alkyl, moiety, denitrogenative, triazol, Intramolecular, rearrangement, replacement
Year: 2012
DOI identifier: 10.1021/ja308285r.s001
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Provided by: FigShare
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