Manganese-Catalyzed Asymmetric Hydrogenation of Quinolines Enabled by π-π Interaction.

The first example of non-noble metal-catalyzed asymmetric hydrogenation of N-heteroaromatics is reported. A new chiral pincer manganese catalyst showed outstanding catalytic activity in the asymmetric hydrogenation of quinolines, affording high yields and enantioselectivities (up to 97% ee). A turnover number of 3840 was reached at a low catalyst loading (S/C=4000), which was competitive with the activity of most effective noble metal catalysts for this reaction. The precise regulation of the enantioselectivity were ensured by a π-π interaction.