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CC BY 4.0 · Synthesis 2025; 57(21): 3227-3232
DOI: 10.1055/a-2616-6753
Paper

Asymmetric Prins Cyclizations of O-Prenylated Salicylaldehydes

Autoren

  • Joyce A. A. Grimm 

    1   Homogenous Catalysis, Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany

  • Benjamin List 

    1   Homogenous Catalysis, Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany

Gefördert durch: Deutsche Forschungsgemeinschaft
Gefördert durch: Horizon 2020 Framework Programme
Max-Planck-Gesellschaft
Deutsche Forschungsgemeinschaft
EXC 2033–390677874–RESOLV
Horizon 2020 Framework Programme
101055472
Generous support from the Max Planck Society, the Deutsche Forschungsgemeinschaft (Germany’s Excellence Strategy-EXC2033-390677874-RESOLV), Advanced Grant Agreement No. 694228 and European Union’s Horizon 2022 research and innovation program “Early Stage Organocatalysis, ESO” Advanced Grant Agreement No. 101055472) is gratefully acknowledged.
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Graphical Abstract

Dedication

Special Topic Dedicated to Prof. Paul Knochel.

Abstract

We report the asymmetric intramolecular Prins cyclization reactions of O-prenylated salicylaldehydes to 4-chromanols. Excellent efficiencies and selectivities were herein obtained using a highly fluorinated imino-imidodiphosphate (iIDP) Brønsted acid catalyst. The presented method tolerates substrates bearing both electron-donating and electron-withdrawing groups.

Keywords

Asymmetric organocatalysis - Imino-imidodiphosphate (iIDP) - Prins cyclization - 4-chromanols - O-prenylated salicylaldehydes

Supplementary Material



Publikationsverlauf

Eingereicht: 03. März 2025

Angenommen: 06. März 2025

Artikel online veröffentlicht:
08. August 2025

© 2025. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting unrestricted use, distribution, and reproduction so long as the original work is properly cited. (https://creativecommons.org/licenses/by/4.0/).

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