Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized Cycloalkenes to Access Chiral 2-Aryl Tetralins.

The transition-metal catalyzed asymmetric hydrogenation of unfunctionalized alkenes is challenging. Herein, we report an efficient iridium-catalyzed asymmetric hydrogenation of unfunctionalized cycloalkenes, delivering chiral 2-aryl tetralins in excellent yields and with moderate to excellent enantioselectivities. The reaction can be performed on a gram-scale with a low catalyst loading (S/C = 1000), and the reduced product was obtained without erosion of the enantioselectivity. Deuterium experiments indicated that the C═C bond in the substrate is hydrogenated directly without isomerization.