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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

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α-Verzweigung erforderlich: Die erste hoch enantioselektive Aktivierung von α-substituierten α,β-ungesättigten Aldehyden mit einem Aminkatalysator wird vorgestellt. Das chirale primäre Amin 1 aktiviert selektiv α-verzweigte Enale für eine Iminiumion/Enamin-Sequenz in Reaktionskaskaden aus Friedel-Crafts- oder Sulfa-Michael-Reaktion und Aminierung. Die hoch funktionalisierten Produkte mit zwei benachbarten Stereozentren werden mit hohen Enantiomerenüberschüssen isoliert.

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