The unique physico-chemical properties of the fluorine atom provide compounds with excellent pharmacokinetic properties, which make them important for drug design. Moreover, organofluorine compounds are also frequently encountered in agrochemicals and materials. Propargylic ethers and amines are synthetically important, as they combine the rigidity, electronic properties and easy post-functionalization of alkynes with the nucleophilic and hydrogen bonding properties of the heteroatoms. Combined with a trifluoromethyl group, valuable building blocks for synthetic and medicinal chemistry are therefore obtained. Due to the different bioactivity of enantiomeric compounds, the synthesis of enantioenriched trifluoromethylated carbinols and anilines has attracted especially attention recently (Scheme 1A). Traditional approaches to these compounds are based on the use of chiral catalysts in (a) the addition of CF3-based nucleophiles to ynones (e.g. Rupert-Prakash reagent), the addition of acetylides onto carbonyl compounds or imines, 9,10 (c) the addition of carbon nucleophiles to trifluoromethylated alkynyl ketones and the reduction of the corresponding trifluoromethylated propargyl imines or (d) via kinetic resolution of the propargyl alcohols. 6a Nevertheless, in some cases stoichiometric amounts of strong bases, lower or higher temperatures, expensive catalysts (Rh, Pd, among others), and/or additives are needed. Furthermore, these protocols often present a narrow scope. Finally, most methods give access only to alcohols, requiring extra synthetic steps if the ethers are targeted. Therefore, the development of new stereoselective strategies for the synthesis of trifluoromethylated propargylic compounds is needed.