An efficient gold-catalyzed synthesis of substituted 3-methylene-3,4-dihydrobenzo[b]oxepinones from ortho-O-propargyl substituted aryl enaminones has been achieved. In this transformation a new C-C bond formation occurred regioselectively via 7-exo-dig cyclization. Benzooxepinone derivatives were obtained in good to excellent yields in a one-pot synthesis at ambient temperature.

A gold(I) catalysed reaction between N-propargylic β-enaminones and arynes was developed to access 3-methylene-1-pyrrolines. The title compounds were obtained in 57-78% yields. This reaction is useful for the generation of substituted 1-pyrrolines exhibiting significant molecular complexity.

An efficient gold-catalyzed intramolecular cyclization of ortho-O-propargyl-1-one substituted arylaldehydes has been achieved for the generation of substituted aroylbenzo[b]oxepin-3-one derivatives in moderate to good yields. This synthetic transformation proceeds via gold-catalysed oxidation of the internal alkyne moiety followed by an intramolecular condensation leading to seven-membered oxacycles.