(<i>Z</i>)-5-Benzylidene-4-phenyl-2-(<i>p</i>-tolyl)-4,5-dihydrooxazole

Abstract

By strategic use of the valence difference between hard gold(III) and soft gold(I) catalysts, one-pot synthesis of (Z)-5-benzylidene-4-phenyl-2-(p-tolyl)-4,5-dihydrooxazole (15) from propargylic alcohol (9) and p-toluamide (13) was achieved via gold(III)-catalyzed propargylic substitution followed by gold(I)-catalyzed cyclization. The structure of 15 was confirmed by X-ray crystallographic analysis.

Keywords

• gold catalysts
• propargylic substitution
• cyclization