In summary, we have developed an innovative strategy to control the stereoselectivity of asymmetric transformations. Our approach first capitalizes on the tools of asymmetric catalysis to forge a chiral oxazolidine from broadly available propargylic amines. This stereogenic element is then used to control the selectivity of the asymmetric hydrogenation of the tetrasubstituted double bond, giving access to valuable chiral amino alcohol precursors. Key for success was the first use of a "truncated" monophosphine Trost-type ligand to induce high enantioselectivity in an unprecedented DYKAT process. Combined with a Sonogashira cross-coupling, our approach gives a stereodivergent access to the four stereoisomers of protected diaryl amino alcohols in high yield and enantioselectivity. New opportunities for the design and development of asymmetric functionalizations of olefins can be expected based on the combination of the enantioselective introduction of a transient chiral auxiliary followed by a diastereoselective transformation. Such processes are currently under investigation in our laboratory. Scheme 5. Diastereo-and enantiodivergent access to chiral aminoalcohol precursors. See SI for detailed reaction conditions. Supporting Information. Experimental procedures and characterization data for starting materials, ligands and products. Proposed reaction mechanism. Copy of HPLC and NMR spectra. Crystallographic data for the product 4 and 5 have been deposited at the Cambridge Crystallographic Data Centre, accession numbers CCDC 2020478 and 2020479, respectively. This material is available free of charge via the Internet at .