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CC BY 4.0 · Synthesis
DOI: 10.1055/a-2616-6753
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Published as part of the Special Topic Dedicated to Prof. Paul Knochel

Asymmetric Prins Cyclizations of O-Prenylated Salicylaldehydes

Joyce A. A. Grimm 
1   Organische Chemie, RWTH Aachen University, Aachen, Germany
,
Benjamin List 
2   Homogenous Catalysis, Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
› Author Affiliations
Supported by: Deutsche Forschungsgemeinschaft
Supported by: 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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Dedication

Dedicated to Professor Paul Knochel on the occasion of his 70th birthday.

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



Publication History

Received: 03 March 2025

Accepted: 06 March 2025

Article published online:
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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