Catalytic Asymmetric Hydrogenation of Polycyclic Aromatic Compounds

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Hydrogenations of 2,6- or 2,7-disubstituted naphthalenes proceeded in high yields with high enantioselectivity in the presence of the ruthenium complex which was chelated with the optically active bisphosphine, PhTRAP. The catalytic asymmetric hydrogenation produced optically active tetralines with up to 92% ee. The chiral ruthenium catalyst is also effective for the hydrogenation of quinolines to give 5,6,7,8-tetrahydroquinolines selectively. The asymmetric hydrogenation proceeded with up to 84% ee.