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Synlett 2024; 35(08): 903-907
DOI: 10.1055/a-2268-4678
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Special Issue dedicated to Keith Fagnou

Manganese(I)-Catalyzed C–H Allylation of Tryptophans and Their Oligopeptides On Water

Julia Struwe
a   Institut für Organische und Biomolekulare Chemie, Wöhler-Forschungsinstitut für Nachhaltige Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
,
Tsuyoshi Oyama
a   Institut für Organische und Biomolekulare Chemie, Wöhler-Forschungsinstitut für Nachhaltige Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
,
Fabrice Gallou∗
b   Chemical & Analytical Development, Novartis Pharma AG, 4056 Basel, Switzerland
,
Lutz Ackermann  ∗
a   Institut für Organische und Biomolekulare Chemie, Wöhler-Forschungsinstitut für Nachhaltige Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
c   German Center for Cardiovascular Research (DZHK), Potsdamer Straße 58, 10785, Berlin, Germany
› Author AffiliationsGenerous support from the Deutsches Zentrum für Herz-Kreislaufforschung (DZHK) (PI at the German Centre for Cardiovascular Research), the European Research Council (ERC) (Advanced Grant 101021358), and the DFG (Gottfried-Wilhelm-Leibniz Prize) to L.A. are gratefully acknowledged. We are also grateful for support from the European Union’s Horizon 2020 research and innovation program, H2020 Marie Skłodowska-Curie Actions (Grant Agreement No. 860762) to T.O., and warmly acknowledge Novartis for financial support.
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Abstract

The manganese(I)-catalyzed allylation of the amino acid tryptophan is realized under exceedingly mild conditions using water as a sustainable and non-hazardous reaction medium, instead of classical organic solvents, with great potential for green and sustainable chemistry. Synthetically useful α,β-unsaturated esters can be accessed by reaction with Morita–Baylis–Hillman (MBH) adducts following a fast C–H activation approach. The robustness of this procedure is reflected by kinetic analysis at different reaction temperatures and reduced catalyst loadings are employed.

Key words

C–H activation - on water - peptides - manganese catalysis - late-stage functionalization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2268-4678.
  • Supporting Information


Publication History

Received: 21 January 2024

Accepted after revision: 14 February 2024

Accepted Manuscript online:
14 February 2024

Article published online:
27 February 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
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