Chiral Bis(oxazoline)-Copper Complex Catalyzed Asymmetric Alkenylation of Isatin Imines and 3-Vinylindoles for Construction of Optically Active 3-Alkenyl-3-aminooxindoles.

The first catalytic asymmetric alkenylation of isatin imines is described. The reaction, which is promoted by a chiral bis(oxazoline)-copper complex, gives structurally diverse 3-alkenyl-3-aminooxindole derivatives in excellent yields, and with excellent diastereoselectivities and high-to-excellent enantioselectivities. The products can be readily converted to polycyclic indole derivatives without loss of enantioselectivity. A plausible chirality-induced mechanism is proposed to explain the observed stereoselective control.