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The Catalytic Asymmetric Fischer Indolization

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Müller,  Steffen
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Webber,  Matthew J.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Müller, S., Webber, M. J., & List, B. (2011). The Catalytic Asymmetric Fischer Indolization. Journal of the American Chemical Society, 133(46), 18534-18537. doi:10.1021/ja2092163.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002A-54A6-D
Abstract
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.