Asymmetric Organocatalytic Cascade Reactions with α-Substituted α,β-Unsaturated Aldehydes

Authors

  • Patrizia Galzerano,

    1. Dipartimento di Chimica Organica “A. Mangini”, Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy)
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    • These authors contributed equally to this work.

  • Fabio Pesciaioli,

    1. Dipartimento di Chimica Organica “A. Mangini”, Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy)
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    • These authors contributed equally to this work.

  • Andrea Mazzanti Dr.,

    1. Dipartimento di Chimica Organica “A. Mangini”, Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy)
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  • Giuseppe Bartoli Prof.,

    1. Dipartimento di Chimica Organica “A. Mangini”, Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy)
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  • Paolo Melchiorre Prof. Dr.

    1. Dipartimento di Chimica Organica “A. Mangini”, Alma Mater Studiorum—Università di Bologna, Viale Risorgimento 4, 40136 Bologna (Italy)
    2. ICREA Research Prof. at the Institute of Chemical Research of Catalonia (ICIQ), Avda. Països Catalans 16, 43007 Tarragona (Spain)
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  • This work was supported by Bologna University and by MIUR National Project “Stereoselezione in Sintesi Organica”.

Abstract

original image

Time to α-branch out! The first highly enantioselective aminocatalytic activation of α-substituted α,β-unsaturated aldehydes is presented. The chiral primary amine 1 selectively activates α-branched enals toward a well-defined iminium ion/enamine reaction sequence for both Friedel–Crafts/amination and sulfa-Michael/amination cascades. The valuable multifunctional products, having two contiguous sterocenters, are isolated in high enantiomeric purity.

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