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

3 Citations (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

Keywords

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

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