Gold Catalysis: Mild Conditions for the Synthesis of Oxazoles from N-Propargylcarboxamides and Mechanistic Aspects
Organic Letters2004Vol. 6(23), pp. 4391–4394
Citations Over TimeTop 1% of 2004 papers
Abstract
2,5-Disubstituted oxazoles are synthesized from the corresponding propargylcarboxamides under mild reaction conditions via homogeneous catalysis by AuCl(3). While monitoring the conversion via (1)H 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 degrees C for several weeks. Deuteration experiments show a stereospecific mode of the two first steps of the reaction.
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