ja308285r_si_001.pdf (5.99 MB)
Synthesis of Enaminones by Rhodium-Catalyzed Denitrogenative Rearrangement of 1‑(N‑Sulfonyl-1,2,3-triazol-4-yl)alkanols
journal contribution
posted on 2012-10-24, 00:00 authored by Tomoya Miura, Yuuta Funakoshi, Masao Morimoto, Tsuneaki Biyajima, Masahiro MurakamiEnaminones 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.