Synergy, Compatibility, and Innovation: Merging Lewis Acids with Stereoselective Enamine Catalysis

Authors

  • Dr. Andrea Gualandi,

    1. Dipartimento di Chimica “G. Ciamician”, ALMA MATER STUDIORUM, Università di Bologna, Via Selmi 2, 44126, Bologna (Italy), Fax: (+39) 0512099456
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  • Luca Mengozzi,

    1. Dipartimento di Chimica “G. Ciamician”, ALMA MATER STUDIORUM, Università di Bologna, Via Selmi 2, 44126, Bologna (Italy), Fax: (+39) 0512099456
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  • Claire M. Wilson,

    1. Centre for Synthesis and Chemical Biology, University College Dublin, Belfield, Dublin 4 (Ireland)
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  • Prof. Pier Giorgio Cozzi

    Corresponding author
    1. Dipartimento di Chimica “G. Ciamician”, ALMA MATER STUDIORUM, Università di Bologna, Via Selmi 2, 44126, Bologna (Italy), Fax: (+39) 0512099456
    • Dipartimento di Chimica “G. Ciamician”, ALMA MATER STUDIORUM, Università di Bologna, Via Selmi 2, 44126, Bologna (Italy), Fax: (+39) 0512099456

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Abstract

In recent years there has been an accelerated rate of development in the field of organocatalysis, with asymmetric organocatalysis now reaching full maturity. The invention of new organocatalytic reactions and the exploration of new concepts now appear in tandem with the application of organocatalytic techniques in the synthesis of natural products and active pharmaceutical ingredients (APIs). After a “golden rush” in organocatalysis, researchers are now starting to combine different methods, thereby taking advantage of the significant benefits of synergy. Metals are used in combination with organocatalytic processes, thus reaching complexity that is found in nature, where enzymes take advantage of the presence of certain metals to increase the arsenal of organic transformations available. In this Focus review, we illustrate the possibility of a “happy marriage” between Lewis acids and organocatalytic stereoselective processes. Questions have been raised about the combination of Lewis acids and organocatalysis owing to the presence of water and/or strong bases in these processes. Some Lewis acids have been shown to be compatible with organocatalysis and concepts relating to their use will be illustrated herein. To summarize the fruitful use of Lewis acids in stereoselective organocatalytic processes, we will draw attention to the advantages and selectivity achieved using this method.

Abstract

I principi di attivazione dell′organocatalisi, amminocatalisi, catalisi via legame idrogeno, catalisi via acidi di Brønsted solo per citarne alcuni, hanno contribuito in anni recenti allo sviluppo esponenziale del′organocatalisi stereoselettiva. La nuova frontiera di sviluppo dell′organocatalisi è però rappresentata dalla sinergia con altri sistemi catalitici, in particolare, con sistemi contenenti metalli. Tra metalli di transizione e non, l′impiego di acidi di Lewis nelle reazioni organocatalitiche rappresenta un fertile campo di innovazione, dove concetti quali sinergia e compatibilità sono sapientemente adoperati nell′invenzione di nuove reazioni.

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