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Direct Regio-, Diastereo-, and Enantioselective Vinylogous Michael Addition of Prochiral 3-Alkylideneoxindoles to Nitroolefins

Authors

  • Gloria Rassu,

    Corresponding author
    1. Istituto di Chimica Biomolecolare del CNR, Traversa La Crucca 3, I-07100 Li Punti Sassari, Italy, Fax: (+39)-079-2841299; phone: (+39)-079-2841226
    • Istituto di Chimica Biomolecolare del CNR, Traversa La Crucca 3, I-07100 Li Punti Sassari, Italy, Fax: (+39)-079-2841299; phone: (+39)-079-2841226
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  • Vincenzo Zambrano,

    1. Istituto di Chimica Biomolecolare del CNR, Traversa La Crucca 3, I-07100 Li Punti Sassari, Italy, Fax: (+39)-079-2841299; phone: (+39)-079-2841226
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  • Luigi Pinna,

    1. Dipartimento di Chimica e Farmacia, Università degli Studi di Sassari, Via Vienna 2, I-07100 Sassari, Italy
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  • Claudio Curti,

    Corresponding author
    1. Dipartimento di Farmacia, Università degli Studi di Parma, Parco Area delle Scienze 27A, I-43124 Parma, Italy, Fax: (+39)-0521-905006; phone: (+39)-0521-905079
    • Dipartimento di Farmacia, Università degli Studi di Parma, Parco Area delle Scienze 27A, I-43124 Parma, Italy, Fax: (+39)-0521-905006; phone: (+39)-0521-905079
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  • Lucia Battistini,

    1. Dipartimento di Farmacia, Università degli Studi di Parma, Parco Area delle Scienze 27A, I-43124 Parma, Italy, Fax: (+39)-0521-905006; phone: (+39)-0521-905079
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  • Andrea Sartori,

    1. Dipartimento di Farmacia, Università degli Studi di Parma, Parco Area delle Scienze 27A, I-43124 Parma, Italy, Fax: (+39)-0521-905006; phone: (+39)-0521-905079
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  • Giorgio Pelosi,

    1. Dipartimento di Chimica, Università degli Studi di Parma, Parco Area delle Scienze 17A, I-43124 Parma, Italy
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  • Franca Zanardi,

    1. Dipartimento di Farmacia, Università degli Studi di Parma, Parco Area delle Scienze 27A, I-43124 Parma, Italy, Fax: (+39)-0521-905006; phone: (+39)-0521-905079
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  • Giovanni Casiraghi

    Corresponding author
    1. Dipartimento di Farmacia, Università degli Studi di Parma, Parco Area delle Scienze 27A, I-43124 Parma, Italy, Fax: (+39)-0521-905006; phone: (+39)-0521-905079
    • Dipartimento di Farmacia, Università degli Studi di Parma, Parco Area delle Scienze 27A, I-43124 Parma, Italy, Fax: (+39)-0521-905006; phone: (+39)-0521-905079
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Abstract

3-Alkylidene-2-oxindoles represent a simple, yet enabling subfamily of indole alkaloids, and their ability to react as electron-poor acceptors has largely been investigated. In contrast, their utility as pronucleophilic synthons remains elusive. In this context, the present article describes the successful execution of the direct, organocatalytic asymmetric Michael addition of prochiral 3-alkylideneoxindoles to nitroolefins. A variety of γ-substituted alkylideneoxindoles carrying two stereocenters at both the γ- and δ-carbon sites was assembled with excellent stereoselectivity and without olefin isomerization or stereochemical ablation.

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