To implement our concept, we considered the palladium-catalyzed carboetherification of propargylic amines, based on the use of trifluoroacetaldehyde-derived tethers (Scheme 1D). The stereocenter formed in this step could direct a subsequent functionalization of the double bond, acting de facto as a chiral auxiliary. The rigid nature of the oxazolidine scaffold containing the stereocenter should secure high level of diasteroselectivity to the following transformations. Concerning the following diastereoselective functionalization, we found the hydrogenation of the formed double bond particularly attractive. Indeed, the enantioselective hydrogenation of alkyl-or heteroatom-tetrasubstituted olefins is highly challenging, with only few limited catalytic enantioselective systems reported. After removal of the tether molecule, this process would provide amino alcohols, key building blocks in synthetic and medicinal chemistry, which have been the focus of intensive methodology development recently. In particular, the diaryl-substituted amino alcohols obtained using this strategy can be found in antidepressants and have served as intermediates for the synthesis of antimycotic, antibacterials and antiviral molecules. However, the selective synthesis of one of the four possible stereoisomers of the amino alcohols generally requires multi-step processes.