Propargylic alcohols are readily available alkynes with an adjacent alcohol group which are versatile building blocks due to their diverse reactivity. Through a wide array of different catalytic transformations, using transition metals or organocatalysis, important synthetic targets can be accessed including enones, furans, carbonates, oxazolidinones or geminal dihalides. Our group ) has developed a range of methodologies to valorize these molecules, using the Gagosz catalyst (PPh3AuNTf2) under mild conditions. This same catalyst is also known to catalyze hydration reactions of propargylic alcohols containing terminal alkynes to yield α-hydroxy ketones. Scheme 1 Hydroamination of alkynes As we had previously observed that propargylic alcohols often show high regioselectivity in a range of gold-catalysed reactions, we set out to investigate a general protocol for the hydroamination of propargylic alcohols. Our first approach was to examine the catalytic activity of PPh3AuNTf2 ([Au]) for hydroamination of a model propargylic alcohol (1a). In an initial experiment, reaction of propargylic alcohol, aniline and 2 mol% of [Au] catalyst at room temperature in CH2Cl2 complete conversion of starting material was observed in 24 h, with the formation of three products: 3-hydroxyimine 1b, 3-hydroxyketone 1c and 3-aminoketone 1d in a ratio of 47:47:6 (1b:1c:1d). Pleasingly, no trace of the regioisomeric products (β-hydroxyimine, β-hydroxyketone) resulting from addition of the aniline to the other carbon of the alkyne were detected. We then decided to explore the reation conditions to determine if it was possible to selectively obtain each of the three products.