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Enhancing the potential of enantioselective organocatalysis with light

Nature volume 554, pages 41–49 (2018)Cite this article

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Abstract

Organocatalysis—catalysis mediated by small chiral organic molecules—is a powerful technology for enantioselective synthesis, and has extensive applications in traditional ionic, two-electron-pair reactivity domains. Recently, organocatalysis has been successfully combined with photochemical reactivity to unlock previously inaccessible reaction pathways, thereby creating new synthetic opportunities. Here we describe the historical context, scientific reasoning and landmark discoveries that were essential in expanding the functions of organocatalysis to include one-electron-mediated chemistry and excited-state reactivity.

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Figure 1: Merging photoredox and enamine catalysis.
Figure 2: Merging photoredox and covalent organocatalysis.
Figure 3: Merging photoredox and non-covalent organocatalysis.
Figure 4: Excited-state reactivity of chiral organocatalytic intermediates.
Figure 5: Non-covalent interactions in enantioselective photochemistry.

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Acknowledgements

P.M. thanks the Generalitat de Catalunya (CERCA Program), Agencia Estatal de Investigación (AEI) (CTQ2016-75520-P), and the European Research Council (ERC 681840-CATA-LUX) for financial support. M.S. thanks the EU for a Horizon 2020 Marie Skłodowska-Curie Fellowship (grant 744242).

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  1. School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, UK

    Mattia Silvi

  2. ICIQ, Institute of Chemical Research of Catalonia—the Barcelona Institute of Science and Technology, Avenida Països Catalans 16, Tarragona, 43007, Spain

    Paolo Melchiorre

  3. ICREA, Catalan Institution for Research and Advanced Studies, Passeig Lluís Companys 23, Barcelona, 08010, Spain

    Paolo Melchiorre

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P.M. outlined the content of the Review and defined its scope. M.S. and P.M. worked together to prepare and edit the manuscript, figures and references.

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Silvi, M., Melchiorre, P. Enhancing the potential of enantioselective organocatalysis with light. Nature 554, 41–49 (2018). https://doi.org/10.1038/nature25175

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