TY - JOUR AU - Kozma, Viktória AU - Szőllősi, György TI - Új katalitikus rendszerek alkalmazása aszimmetrikus Michael-addíciókban maleimidekre JF - MAGYAR KÉMIAI FOLYÓIRAT - KÉMIAI KÖZLEMÉNYEK (1997-) J2 - MAGY KÉM FOLY KÉM KÖZL VL - 129 PY - 2023 IS - 3-4 SP - 139 EP - 146 PG - 8 SN - 1418-9933 DO - 10.24100/MKF.2023.03-04.139 UR - https://m2.mtmt.hu/api/publication/34483761 ID - 34483761 N1 - "Kozma Viktória azonos című PhD értekezése és a kapcsolódó tézisfüzet alapján készült." LA - Hungarian DB - MTMT ER - TY - THES AU - Kozma, Viktória TI - Új katalitikus rendszerek alkalmazása aszimmetrikus Michael-addíciókban maleimidekre [Application of new catalytic systems in asymmetric Michael additions to maleimides] PB - Szegedi Tudományegyetem PY - 2022 SP - 115 DO - 10.14232/phd.11305 UR - https://m2.mtmt.hu/api/publication/34121002 ID - 34121002 LA - Hungarian DB - MTMT ER - TY - JOUR AU - Kozma, Viktória AU - Szakonyi, Zsolt AU - Szőllősi, György TI - β-Amino Acid Organocatalysts in the Asymmetric Michael Addition of Isobutyraldehyde to N-Substituted Maleimides JF - CATALYSTS J2 - CATALYSTS VL - 12 PY - 2022 IS - 9 PG - 13 SN - 2073-4344 DO - 10.3390/catal12090992 UR - https://m2.mtmt.hu/api/publication/33080561 ID - 33080561 N1 - Cited By :1 Export Date: 15 July 2024 Correspondence Address: Szakonyi, Z.; Institute of Pharmaceutical Chemistry, Eötvös utca 6, Hungary; email: szakonyi.zsolt@szte.hu Correspondence Address: Szőllősi, G.; ELKH-SZTE, Eötvös utca 6, Hungary; email: szollosi@chem.u-szeged.hu Funding details: Hungarian Scientific Research Fund, OTKA, K 138871 Funding details: Hungarian Science Foundation Funding text 1: This research was supported by the Hungarian Science Foundation, grant number OTKA K 138871. AB - Asymmetric Michael additions of carbonyl compounds to N-substituted maleimides are among the most convenient reactions to prepare optically pure succinimide building blocks. Although a few β-amino acids were found to be highly efficient organocatalysts in the addition of α-branched aldehydes, the effect of their structure on the results of these reactions has not yet been investigated. In the present study, we disclose several unexpected and interesting structural effects of aliphatic and cycloaliphatic β-amino acids obtained in the enantioselective conjugate addition of isobutyraldehyde to N-benzylmaleimide. The dependence of the sense of the enantioselectivity on the bulkiness of the substituent on the β-carbon atom, the beneficial spatial arrangements of the functional groups in cis isomers with cyclohexane scaffold and the inversion of the enantioselectivity depending on the absence of a base additive observed with some trans isomers are unprecedented findings. The minor influence of the nitrogen substituent of the maleimide ring on both the reaction rate and the enantioselectivity was also evidenced using alicyclic β-amino acid prepared from an easily available terpene derivative. LA - English DB - MTMT ER - TY - JOUR AU - Kozma, Viktória AU - Szőllősi, György TI - Enantioselective Michael addition of aldehydes to maleimides catalysed by surface-adsorbed natural amino acids JF - CATALYSIS SCIENCE & TECHNOLOGY J2 - CATAL SCIENCE & TECHNOLOGY VL - 12 PY - 2022 IS - 15 SP - 4709 EP - 4726 PG - 18 SN - 2044-4753 DO - 10.1039/d2cy00545j UR - https://m2.mtmt.hu/api/publication/32936771 ID - 32936771 N1 - Cited By :8 Export Date: 15 July 2024 CODEN: CSTAG Correspondence Address: Szollosi, G.; SZTE-ELKH Stereochemistry Research Group, Eötvös utca 6, Hungary; email: szollosi@chem.u-szeged.hu Funding details: 20391-3/2018/FEKUSTRAT Funding details: Hungarian Scientific Research Fund, OTKA, K 138871 Funding details: Hungarian Science Foundation Funding text 1: Financial support by the Hungarian Ministry of Human Capacities through grant 20391-3/2018/FEKUSTRAT is highly appreciated. Financial support of the Hungarian Science Foundation through OTKA Grant K 138871 is acknowledged. The authors thank Dr. Gábor Varga, Dr. Márton Szabados, Dr. Rebeka Mészáros, Prof. Ákos Kukovecz and Prof. Zoltán Kónya for their valuable help in characterizing the hybrid materials. AB - Asymmetric Michael addition of carbonyl compounds to N-substituted maleimides is an important method for obtaining optically pure succinimides, which are important chiral fine chemical intermediates. Environmentally friendly and sustainable procedures require the use of a heterogeneous, recyclable catalyst obtained from natural chirality sources and cheap auxiliaries. Here we report the application of in situ formed chiral inorganic-organic hybrid catalysts using amino acids such as l-phenylalanine and clay minerals or alumina, which were highly active and provided excellent enantioselectivities, up to 99%, in the addition of aldehydes to a large variety of N-substituted maleimides. Examinations indicated the occurrence of the asymmetric reaction on the surface of the recyclable solid hybrid materials. The catalytic materials were examined by thermogravimetry, XRD, FT-IR and Raman spectroscopy, SEM and adsorption experiments. Results of these methods showed that the amino acid is deposited as surface crystallites or intercalated in the layered cation exchangers, which both function as a supply of the chirality source, whereas the reactions are catalysed by the chiral compounds adsorbed on the surface. This catalytic system was used to conveniently prepare chiral succinimides at the gram scale, easily purified by crystallization. Accordingly, these chiral hybrid materials are convenient heterogeneous catalysts for obtaining valuable compounds in high optical purities using natural chirality sources, inorganic solids and ethyl acetate, a green organic solvent. LA - English DB - MTMT ER - TY - JOUR AU - Kozma, Viktória AU - Szőllősi, György TI - Conjugate addition of 1,3-dicarbonyl compounds to maleimides using bifunctional primary amine‒(thio)phosphoramide organocatalysts JF - MOLECULAR CATALYSIS J2 - MOL CATAL VL - 518 PY - 2022 PG - 13 SN - 2468-8231 DO - 10.1016/j.mcat.2021.112089 UR - https://m2.mtmt.hu/api/publication/32555761 ID - 32555761 N1 - Cited By :7 Export Date: 15 July 2024 CODEN: MCOAD Correspondence Address: Szőllősi, G.; Stereochemistry Research Group of the Hungarian Academy of Sciences, Eötvös utca 6, Hungary; email: szollosi@chem.u-szeged.hu Funding details: 20391 Funding details: Hungarian Scientific Research Fund, OTKA, K 138871 Funding details: Nemzeti Kutatási, Fejlesztési és Innovaciós Alap, NKFIA Funding details: Innovációs és Technológiai Minisztérium Funding text 1: Financial support by the ÚNKP-21–3-SZTE-440 New National Excellence Program of the Ministry for Innovation and Technology from the source of the National Research, Development and Innovation Fund (V. Kozma) and by the Hungarian Ministry of Human Capacities through grant 20391–3/2018/FEKUSTRAT is highly appreciated. Financial support of the Hungarian National Science Foundation through OTKA Grant K 138871 is acknowledged. LA - English DB - MTMT ER - TY - CHAP AU - Kozma, Viktória AU - Szőllősi, György ED - Alapi, Tünde ED - Berkecz, Róbert ED - Ilisz, István TI - NATURAL CHIRAL CATALYSTS ON SOLID SURFACES USED IN MICHAEL ADDITION TO MALEIMIDES T2 - Proceedings of the 27th International Symposium on Analytical and Environmental Problems PB - University of Szeged CY - Szeged SN - 9789633068359 PY - 2021 SP - 193 EP - 197 PG - 5 UR - https://m2.mtmt.hu/api/publication/32525198 ID - 32525198 LA - English DB - MTMT ER - TY - CHAP AU - Kozma, Viktória AU - Szőllősi, György ED - Alapi, Tünde ED - Berkecz, Róbert ED - Ilisz, István TI - Phosphoramide chiral catalysts for environmentally friendly asymmetric organocatalytic processes T2 - Proceedings of the 26th International Symposium on Analytical and Environmental Problems PB - University of Szeged CY - Szeged SN - 9789633067710 PY - 2020 SP - 35 EP - 39 PG - 5 UR - https://m2.mtmt.hu/api/publication/31719676 ID - 31719676 LA - English DB - MTMT ER - TY - JOUR AU - Kozma, Viktória AU - Fülöp, Ferenc AU - Szőllősi, György TI - 1,2‐Diamine‐Derived (thio)Phosphoramide Organocatalysts in Asymmetric Michael Additions JF - ADVANCED SYNTHESIS & CATALYSIS J2 - ADV SYNTH CATAL VL - 362 PY - 2020 IS - 12 SP - 2444 EP - 2458 PG - 15 SN - 1615-4150 DO - 10.1002/adsc.202000335 UR - https://m2.mtmt.hu/api/publication/31346249 ID - 31346249 N1 - Funding Agency and Grant Number: Ministry of Human Capacities, Hungary [20391-3/2018/FEKUSTRAT, NTP-NFTo-19] Funding text: Financial support of the Ministry of Human Capacities, Hungary through grants 20391-3/2018/FEKUSTRAT and NTP-NFTo-19 (V. Kozma) is acknowledged. LA - English DB - MTMT ER - TY - JOUR AU - Varga, Gábor AU - Kozma, Viktória AU - Kolcsár, Vanessza Judit AU - Kukovecz, Ákos AU - Kónya, Zoltán AU - Sipos, Pál Miklós AU - Pálinkó, István AU - Szőllősi, György TI - β-Isocupreidinate-CaAl-layered double hydroxide composites-heterogenized catalysts for asymmetric Michael addition JF - MOLECULAR CATALYSIS J2 - MOL CATAL VL - 482 PY - 2020 PG - 7 SN - 2468-8231 DO - 10.1016/j.mcat.2019.110675 UR - https://m2.mtmt.hu/api/publication/30849372 ID - 30849372 LA - English DB - MTMT ER - TY - CHAP AU - Kozma, Viktória AU - Szőllősi, György ED - Alapi, Tünde ED - Ilisz, István TI - Asymmetric Michael-additions catalyzed by environmentally benign heterogeneous chiral 1,2-diamine derivatives T2 - Proceedings of the 25th International Symposium on Analytical and Environmental Problems PB - University of Szeged CY - Szeged SN - 9789633067024 PY - 2019 SP - 342 EP - 344 PG - 3 UR - https://m2.mtmt.hu/api/publication/30856152 ID - 30856152 LA - English DB - MTMT ER -