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

Authors :
Nasery, Ashkan
Imanzadeh, Gholamhassan
Zamanloo, Mohammad Reza
Soltanzadeh, Zahra
Öztürk, Turan
Source :
Tetrahedron. Oct2023, Vol. 147, pN.PAG-N.PAG. 1p.
Publication Year :
2023

Abstract

In summary, this paper describes synthesis of a new acidic catalyst to accomplish highly enantioselective Biginelli reactions. Sulfonic-functionalized hyperbranched polylysine (HBPL-SO 3 H) 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. [Display omitted] [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00404020
Volume :
147
Database :
Academic Search Index
Journal :
Tetrahedron
Publication Type :
Academic Journal
Accession number :
172973007
Full Text :
https://doi.org/10.1016/j.tet.2023.133656