Vinylindoles undergo Ni (II)-catalyzed asymmetric hydrovinylation under very mild conditions (− 78° C, 1 atm ethylene, 4 mol% catalyst) to give the corresponding 2-but-3-enyl derivatives in excellent yields and enantioselectivities. Hydroboration of the alkene and oxidation to an acid, followed by Friedel–Crafts annulation, gives an indole-annulated cyclopentanone that is a suitable precursor for the syntheses of cis-trikentrins and all ...