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Synthesis
DOI: 10.1055/a-2815-1115
Paper

Asymmetric Pudovik Reaction as a Tool for Functionalizing 3-Formyl Chromones

Autor*innen

  • Juan Carlos Morales-Solís 

    1   Department of Organic Chemistry, Laboratorio de Organocatálisis Asimétrica, Instituto de Síntesis Química y Catálisis Homogénea (CSIC–University of Zaragoza), Zaragoza, Spain
    2   Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos Centro de Investigaciones Químicas, Cuernavaca, Mexico (Ringgold ID: RIN428215)

  • Mario Ordónez 

    3   Centro de Investigaciones Quimicas, Universidad Autónoma del Estado de Morelos Centro de Investigaciones Químicas, Cuernavaca, Mexico (Ringgold ID: RIN428215)

  • Eugenia Marqués López 

    1   Department of Organic Chemistry, Laboratorio de Organocatálisis Asimétrica, Instituto de Síntesis Química y Catálisis Homogénea (CSIC–University of Zaragoza), Zaragoza, Spain

  • Raquel P. Herrera 

    1   Department of Organic Chemistry, Laboratorio de Organocatálisis Asimétrica, Instituto de Síntesis Química y Catálisis Homogénea (CSIC–University of Zaragoza), Zaragoza, Spain

Gefördert durch: Secretaría de Ciencia, Humanidades, Tecnología e Innovación (SECIHTI) 140607,286614
Gefördert durch: SECIHTI 1004402
Gefördert durch: Agencia Estatal de Investigación MICIU/AEI10.13039/501100011033,PID2023-147471NB-I00
Gefördert durch: Gobierno de Aragón-Fondo Social Europeo (Research Group E07_23R
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We report a preliminary proof of concept for the first asymmetric synthesis of a novel series of chromone-derived compounds via the Pudovik reaction, employing the chiral organocatalyst (DHQ)2Phal. Although only moderate enantiomeric excess values were obtained, the scope of the reaction using different electron-withdrawing and electron-donating groups on substituted 3-formyl chromones demonstrated the viability of this methodology. The absolute configuration of the final products was established through NMR analysis of diastereomeric derivatives with (S) Naproxen, complemented by computational calculations, including a study of the correlation between dipole moment and molecular polarity.



Publikationsverlauf

Eingereicht: 09. Dezember 2025

Angenommen nach Revision: 16. Februar 2026

Accepted Manuscript online:
16. Februar 2026

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