Convenient synthesis and useful application of a series of Josiphos-type binaphane ligands were described. The iridium complexes of these chiral diphosphines displayed excellent enantioselectivity and good reactivity in the asymmetric hydrogenation of challenging 1-aryl-substituted dihydroisoquinoline substrates (full conversions, up to >99% ee, 4000 TON). The use of 40% HBr (aqueous solution) as an additive dramatically improved the asymmetric induction of these catalysts. This transformation provided a highly efficient and enantioselective access to chiral 1-aryl-substituted tetrahydroisoquinolines, which were of great importance and common in natural products and biologically active molecules.

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As a cross-cutting and comprehensive subject, medicinal chemistry involves the knowledge of chemical, biological, medical, and pharmaceutical sciences. A comprehensive medicinal chemistry experience for undergraduates is expected to train various experimental skills and enhance their scientific research ability. Herein, a series of laboratory and computational experiments performed by undergraduate students were described, including synthesis, acetylation, and activity testing of an acetylcholinesterase inhibitor, tacrine. The inhibition activities of tacrine and acetylated tacrine were discussed based on the results of computer simulations. Moreover, representative student-generated data, methods of the experiments, and an interpretation of student feedback on the project are presented.