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Electrochemical synthesis

Radical approach for enantioselective amination

Nature Synthesis (2023)Cite this article

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Enantioselective electrocatalysis is emerging as an increasingly versatile tool in organic synthesis. Now, by applying asymmetric Lewis acid catalysis with an elaborated ligand design, radical electrochemical amination is accomplished with full selectivity control.

Molecular synthesis involving unpaired radical intermediates has gained considerable recent attention because it allows access to uncommon reaction pathways by single electron transfer (SET) and multiple-site concerted proton–electron transfer (MS-CPET). The inherently high reactivity of free radicals naturally creates a challenge for full selectivity control. Electrosynthesis is a well-established tool for the controlled generation of radicals under mild reaction conditions6, and both electrosynthesis and electrocatalysis are experiencing enormous recent growth7. Despite indisputable progress, full selectivity control in enantioselective electrocatalysis continues to be scarce. In this regard, the electrooxidative cross-dehydrogenative amination of carbonyl compounds 1, giving access to highly enantioenriched α-amino carbonyl compounds 3, represents a major advance, as now nicely devised by Guo and co-workers (Fig. 1a).

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Fig. 1: Lewis acid-catalysed electrochemical radical amination as an innovative strategy for the synthesis of enantiomerically enriched α-amino carbonyl compounds.

References

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  1. Wöhler Research Institute for Sustainable Chemistry, Georg-August-Universität Göttingen, Göttingen, Germany

    Tristan von Münchow & Lutz Ackermann

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  1. Tristan von Münchow
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  2. Lutz Ackermann
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Correspondence to Lutz Ackermann.

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The authors declare no competing interests.

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von Münchow, T., Ackermann, L. Radical approach for enantioselective amination. Nat. Synth (2023). https://doi.org/10.1038/s44160-023-00379-3

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  • DOI: https://doi.org/10.1038/s44160-023-00379-3

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