TY - JOUR
T1 - Highly enantioselective Biginelli reaction using sulfonic-functionalized chiral hyperbranched polylysine in absence of solvent
T2 - A new catalyst for asymmetric synthesis of dihydropyrimidinones
AU - Nasery, Ashkan
AU - Imanzadeh, Gholamhassan
AU - Zamanlu, Mohammadreza
AU - Soltanzadeh, Zahra
AU - Öztürk, Turan
N1 - Publisher Copyright:
© 2023 Elsevier Ltd
PY - 2023/10/30
Y1 - 2023/10/30
N2 - 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.
AB - 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.
KW - Asymmetric synthesis
KW - Biginelli reaction
KW - Chiral catalyst
KW - Dihydropyrimidinones
KW - Hyperbranched polylysine
KW - Solvent-free conditions
UR - http://www.scopus.com/inward/record.url?scp=85171980110&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2023.133656
DO - 10.1016/j.tet.2023.133656
M3 - Article
AN - SCOPUS:85171980110
SN - 0040-4020
VL - 147
JO - Tetrahedron
JF - Tetrahedron
M1 - 133656
ER -