Journal of the American Chemical Society, Vol.133, No.46, 18534-18537, 2011
The Catalytic Asymmetric Fischer Indolization
The first catalytic asymmetric Fischer indolization is reported. In the presence of a 5 mol % loading of a novel spirocyclic chiral phosphoric acid, 4-substituted cyclohexanone-derived phenylhydrazones undergo a highly enantioselective indolization. Efficient catalyst turnover was achieved by the addition of a weakly acidic cation exchange resin, which removes the generated ammonia. The reaction. can be conducted under mild conditions and gives various 3-substituted tetrahydrocarbazoles in generally high yields.