Nitrogen atoms play a key role in many biologically active compounds including natural products and pharmaceuticals, and this has encouraged the development of new synthetic strategies to construct C-N bonds. Hydroamination of alkenes or alkynes is an atom economical and direct method to generate C-N bonds which has attracted considerable interest. Although alkenes yield amines directly, the transformation has often proved challenging. On the other hand, the hydroamination of alkynes can be mediated by a range of catalysts based on elements from across the periodic table. This offers an alternative strategy which yields imines or enamines which can be further transformed through sequential reactions to access useful products. A key limitation of the hydroamination of alkynes is the low reactivity of internal alkynes and the poor regioselectivity usually observed with these substrates in intermolecular reactions (Scheme 1). Catalyst design has allowed improved regiocontrol for hydroamination of terminal alkynes, with late transition catalysts usually affording Markovnikov products, whereas early transition-metal catalysts predominantly afford anti-Markovnikov products. Internal alkyne hydroamination selectivity has proved to be more challenging, with reactions usually giving mixtures of isomers. A rare exception is the hydroamination of alkynes bearing strongly electron withdrawing groups, which give high regioselectivities favoring amine attack on the less electron rich atom of the πsystem. In this paper, we describe a highly regioselective hydroamination of propargylic alcohols which can be controlled to provide three different products by varying the reaction conditions.