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Synlett 1991; 1991(3): 147-150
DOI: 10.1055/s-1991-20657
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Transition Metal-Diene Complexes in Organic Synthesis; Part 6.1 Stereoselective Synthesis of Iron-Complexed 4b,8a-Dihydrocarbazol-3-ones: A Novel Route to 4a,9a-Dihydro-9H-carbazoles and Highly Chemo-, Regio-, and Stereoselective Sakurai Reactions

Hans-Joachim Knölker* , Peter G. Jones, Jörn-Bernd Pannek, Andreas Weinkauf
  • *Institut für Organische Chemie der Universität, Schneiderberg 1 B, D-3000 Hannover 1, Germany
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Publication Date:
07 March 2002 (online)

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The reactivity of iron-complexed 4b,8a-dihydrocarbazol-3-ones, prepared from tricarbonyl(cyclohexadienylium)-iron tetrafluoroborate with 4-methoxy-2-methyl- or 4-methoxy-2,3-dimethylaniline and subsequent chemoselective oxidation, has been investigated. Using the tricarbonyliron group as a protecting group for this ring system allows a novel access to the 4a,9a-dihydro-9H-carbazoles and the chemo-, regio-, and stereoselective introduction of an allyl group at C4a of the carbazole nucleus via the Sakurai reaction.

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