Asymmetric Hydrovinylation of Vinylindoles. A Facile Route to Cyclopenta [g] indole Natural Products (+)-cis-Trikentrin A and (+)-cis-Trikentrin B

W Liu, HJ Lim, TV RajanBabu

Index: Liu, Wang; Lim, Hwan Jung; Rajanbabu Journal of the American Chemical Society, 2012 , vol. 134, # 12 p. 5496 - 5499

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Citation Number: 34

Abstract

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 ...