title: Synthesis of enaminones by rhodium-catalyzed denitrogenative rearrangement of 1-(N-sulfonyl-1,2,3-triazol-4-yl)alkanols.
abstract: 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.
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan. tmiura@sbchem.kyoto-u.ac.jp
authors.forename: Tomoya
authors.initials: T
authors.lastname: Miura
authors.forename: Yuuta
authors.initials: Y
authors.lastname: Funakoshi
authors.forename: Masao
authors.initials: M
authors.lastname: Morimoto
authors.forename: Tsuneaki
authors.initials: T
authors.lastname: Biyajima
authors.forename: Masahiro
authors.initials: M
authors.lastname: Murakami
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000588:Amines; D009942:Organometallic Compounds; D012238:Rhodium