Highly Enantioselective\nSynthesis of 3,3-Diarylpropyl\nAmines and 4‑Aryl Tetrahydroquinolines via Ir-Catalyzed Asymmetric\nHydrogenation

Chiral nitrogen-containing compounds are crucial for\nthe chemical,\npharmaceutical, and agrochemical industries. Nevertheless, the synthesis\nof certain valuable scaffolds remains underdeveloped due to the vast\nchemical space available. In this work, we present a diastereoselective\nmethodology for synthesizing 3,3-diarylallyl phthalimides, which,\nfollowing iridium-catalyzed asymmetric hydrogenation using Ir–UbaPHOX,\nyield 3,3-diarylpropyl amines with high enantioselectivity (98–99%\nee). The importance of alkene purity to achieve high enantioselectivity\nis discussed. The synthetic utility of the chiral propylamines obtained\nis demonstrated through the preparation of medicinally useful bioactive\ncompounds like the drugs tolterodine and tolpropamine and 4-aryl tetrahydroquinolines.\nThis strategy enables the synthesis of these compounds with the highest\nenantioselectivity reported to date.