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An Asymmetric Organocatalytic One-Pot Strategy to Octahydroacridines

Authors

  • Gustav Dickmeiss,

    1. Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C (Denmark), Fax: (+45) 8919-6199
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  • Kim L. Jensen,

    1. Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C (Denmark), Fax: (+45) 8919-6199
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  • Dr. Dennis Worgull,

    1. Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C (Denmark), Fax: (+45) 8919-6199
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  • Dr. Patrick T. Franke,

    1. Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C (Denmark), Fax: (+45) 8919-6199
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  • Prof. Dr. Karl Anker Jørgensen

    Corresponding author
    1. Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C (Denmark), Fax: (+45) 8919-6199
    • Center for Catalysis, Department of Chemistry, Aarhus University, 8000 Aarhus C (Denmark), Fax: (+45) 8919-6199
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  • This work was supported by OChemSchool, the Carlsberg Foundation, and the Deutsche Forschungsgemeinschaft (D.W.). We thank Dr. Jacob Overgaard for performing X-ray analysis.

Abstract

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An elegant sequence: An efficient method for the formation of octahydroacridines provides high yields and a high level of stereogenic control, and displays great tolerance towards different aldehydes, anilines, and nucleophiles (see scheme; TMS=trimethylsilyl; EWG=electron-withdrawing group). The use of different nucleophiles verifies an endo transition state in which π–π overlap of the aromatic rings plays an important role in the reactivity and selectivity.

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