Highly enantioselective Biginelli reaction using sulfonic-functionalized chiral hyperbranched polylysine in absence of solvent: A new catalyst for asymmetric synthesis of dihydropyrimidinones

Ashkan Nasery, Gholamhassan Imanzadeh*, Mohammadreza Zamanlu, Zahra Soltanzadeh, Turan Öztürk

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

In summary, this paper describes synthesis of a new acidic catalyst to accomplish highly enantioselective Biginelli reactions. Sulfonic-functionalized hyperbranched polylysine (HBPL-SO3H) as a novel and efficient catalyst help synthesize a series of optically active dihydropyrimidinones via asymmetric synthesis. The reactions carried out under solvent-free conditions at 70 °C within 7 h and produced chiral dihydropyrimidinones in high yields with very good enantiomeric excess. This catalyst could be used at least 5 times without considerable decrease in activity and also induction of chirality. Simple work-up, high yield and enantiomeric excess are some of important advantages of performed reactions with this catalyst. The related organocatalyst was synthesized with 98% yield and its structure was confirmed by IR, NMR, XRD, TGA analysis.

Original languageEnglish
Article number133656
JournalTetrahedron
Volume147
DOIs
Publication statusPublished - 30 Oct 2023

Bibliographical note

Publisher Copyright:
© 2023 Elsevier Ltd

Funding

Authors are thankful of the laboratories of Tehran and Tabriz University as well as University of Mohaghegh Ardabili for the product analysis.

FundersFunder number
University of Mohaghegh Ardabili
laboratories of Tehran and Tabriz University

    Keywords

    • Asymmetric synthesis
    • Biginelli reaction
    • Chiral catalyst
    • Dihydropyrimidinones
    • Hyperbranched polylysine
    • Solvent-free conditions

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