Gold Catalysis:  Mild Conditions for the Synthesis of Oxazoles from N-Propargylcarboxamides and Mechanistic Aspects

Autor: Hashmi, A. S. K., Weyrauch, J. P., Frey, W., Bats, J. W.
Zdroj: Organic Letters; November 2004, Vol. 6 Issue: 23 p4391-4394, 4p
Abstrakt: 2,5-Disubstituted oxazoles are synthesized from the corresponding propargylcarboxamides under mild reaction conditions via homogeneous catalysis by AuCl3. While monitoring the conversion via 1H NMR spectroscopy, an intermediate 5-methylene-4,5-dihydrooxazole can be observed and accumulated up to 95%, being the first direct and catalytic preparative access to such alkylidene oxazolines. The intermediate was fully characterized and can be trapped at −25 °C for several weeks. Deuteration experiments show a stereospecific mode of the two first steps of the reaction.
Databáze: Supplemental Index