Ag- and Au-catalyzed addition of alcohols to ynimides: β-regioselective carbonylation and production of oxazoles.

Takuya Sueda, Arisa Kawada, Yumi Urashi, Naoki Teno

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

Organic letters 2013 Apr 5

filter terms:

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.

Citation

Takuya Sueda, Arisa Kawada, Yumi Urashi, Naoki Teno. Ag- and Au-catalyzed addition of alcohols to ynimides: β-regioselective carbonylation and production of oxazoles. Organic letters. 2013 Apr 5;15(7):1560-3