Various aryl propargylic amines were well tolerated in the reaction, regardless of the position of the substituents on the phenyl ring, as well as their electronic and steric properties (Scheme 3, 4, 6-14). The geometry of the olefin can be switched by just exchanging the aryl group on the alkyne and the aryl iodide (4 vs 6). The reaction tolerates heterocycles such as pyridine and thiophene on the alkyne, although an erosion of the enantioselectivity was observed (15 and 16). Alkyl propargylic amines delivered products 17-19 bearing a methyl, a benzyl and a cyclopropyl group. The reaction could be performed on a 5 mmol scale providing 2.0 grams of 4 (quantitative yield) without erosion of the optical purity. The absolute configuration of the products were assigned by X-ray analysis of 4, confirming in addition that the aryl group coming from the iodide is incorporated in trans position to the oxygen. Scheme 2. (A) X-ray crystal structure of the product 4. (B). Optimized conditions for the diastereoselective hydrogenation.