The alcohol moiety in the propargylic alcohol appears to play an important role in terms of accelerating the hydroamination reaction (Scheme 6). Protection of the propargylic alcohol as a benzyl or trimethylsilyl ether completely inhibits the hydroamination reaction, suggesting that hydrogen bonding between the attacking aryl amine and the OH group of the substrate plays a key role in delivery of the nucleophile to the activated alkyne. The regioselectivity of the nucleophilic attack is probably largely controlled by the electronic effect of the adjacent C-O bond, which disfavors the build-up of positive charge on the adjacent alkyne carbon. After hydroamination and protodeauration, the resulting enamine can tautomerise to the imine which undergoes hydrolysis to yield the hydroxyketone when water is present. Under anhydrous conditions, the imine is stable and can be subsequently reduced to the syn aminoalcohol. The aminoketone product can be obtained via hydroamination of the enone which is formed readily via Meyer-Schuster rearrangement under conditions similar to those we have previously reported. Scheme 6 Plausible reaction mechanisms for the formation of the three different products.