title: Ag- and Au-catalyzed addition of alcohols to ynimides: β-regioselective carbonylation and production of oxazoles.
abstract: Metal-catalyzed reactions of ynimides with alcohols to afford β-ketoimides and oxazoles are demonstrated. The triple bond of ynamides is generally activated by mineral acids or metal salts to lead to the regioselective addition of nucleophiles at the α-C-atom, because of the inherent electronic bias. In contrast, the two neighboring carbonyl groups of ynimides decrease the electron density of the triple bond and the nucleophiles attack the carbonyl C-atom.
authors.affiliation: Faculty of Pharmaceutical of Sciences, Hiroshima International University, 5-1-1 Hirokoshingai, Kure City, Hiroshima 737-0112, Japan. t-sueda@ps.hirokoku-u.ac.jp
authors.forename: Takuya
authors.initials: T
authors.lastname: Sueda
authors.forename: Arisa
authors.initials: A
authors.lastname: Kawada
authors.forename: Yumi
authors.initials: Y
authors.lastname: Urashi
authors.forename: Naoki
authors.initials: N
authors.lastname: Teno
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D007094:Imides / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D012834:Silver / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D007094:Imides; D010080:Oxazoles; D012834:Silver; D006046:Gold