A series of substituted nitrogen-containing 9-membered epoxy vinyl ethers has been constructed from easily available 5-aza-2,3-epoxy-7-yn-1-ols. Attack of the hydroxyl group onto the gold(I)-activated alkyne gave the postulated 9-membered allylic vinyl ether gold intermediate which underwent protodeauration affording the 9-membered epoxy vinyl ethers.Scheme I Gold-catalyzed Claisen-type rearrangements of nitrogen-containing 2-en-7-yn-1ols Scheme II A Postulated reaction path for the formation of cis-3-aroyl-4-vinylpyrrolidine (3) from (Z)-8-aryl-5-azaoct-2-en-7-yn-1-ol (1)