Asymmetric Prins Cyclizations of O-Prenylated Salicylaldehydes

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.

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Publication Details

Journal
Synthesis
Published
2025-08-08
DOI
https://doi.org/10.1055/a-2616-6753
Primary Topic
Synthetic Organic Chemistry Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Asymmetric Prins Cyclizations of O-Prenylated Salicylaldehydes

Benjamin List, Joyce A. A. Grimm
Synthesis
Synthetic Organic Chemistry Methods
article

Asymmetric Prins Cyclizations of O-Prenylated Salicylaldehydes

Benjamin List, Joyce A. A. Grimm
article en

Abstract

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.

Synthesis
Max-Planck-Institut für Kohlenforschung (DE), RWTH Aachen University (DE)
European Commission, Deutsche Forschungsgemeinschaft, Max-Planck-Gesellschaft, Horizon 2020 Framework Programme
Openalex Percentile: Top 85%
Synthetic Organic Chemistry Methods
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