TY - JOUR AU - Varga, Bence AU - Buna, Levente AU - Vincze, Daniella AU - Holczbauer, Tamás AU - Mátravölgyi, Béla AU - Fogassy, Elemér AU - Keglevich, György AU - Bagi, Péter TI - Enantioseparation of P-Stereogenic 1-Adamantyl Arylthiophosphonates and Their Stereospecific Transformation to 1-Adamantyl Aryl-H-phosphinates JF - MOLECULES J2 - MOLECULES VL - 28 PY - 2023 IS - 4 PG - 14 SN - 1431-5157 DO - 10.3390/molecules28041584 UR - https://m2.mtmt.hu/api/publication/33635097 ID - 33635097 N1 - Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3, Budapest, H-1111, Hungary Center for Structural Science, Chemical Crystallography Research Laboratory and Institute for Organic Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2, Budapest, H-1519, Hungary Export Date: 20 March 2023 CODEN: MOLEF Correspondence Address: Varga, B.; Department of Organic Chemistry and Technology, Műegyetem rkp. 3, Hungary; email: bencevarga@edu.bme.hu Correspondence Address: Bagi, P.; Department of Organic Chemistry and Technology, Műegyetem rkp. 3, Hungary; email: bagi.peter@vbk.bme.hu AB - A focused library of 1-adamantyl arylthiophosphonates was prepared in racemic form. An enantioseparation method was developed for P-stereogenic thiophosphonates using (S)-1-phenylethylamine as the resolving agent. Under optimized conditions, three out of the five arylthiophosphonates were prepared in enantiopure form (ee > 99%). The subsequent desulfurization of optically active arylthiophosphonates gave the corresponding H-phosphinates without significant erosion of enantiomeric purity (ee = 95–98%). Hence, this reaction sequence can be considered an alternative method for the preparation of 1-adamantyl aryl-H-phopshinates. The absolute configuration of the (S)-1-adamantyl phenylphosphonothioic acid was assigned using single-crystal XRD and it allowed the confirmation that the removal of the P = S group proceeds with retention of configuration. The organocatalytic applicability of (S)-1-adamantyl phenylphosphonothioic acid was also evaluated as a P-stereogenic Brønsted acid. LA - English DB - MTMT ER - TY - THES AU - Varga, Bence TI - P-Sztereogén centrumot tartalmazó H-foszfinátok, szekunder- és tercier foszfin-oxidok rezolválása és felhasználása PB - Budapesti Műszaki és Gazdaságtudományi Egyetem PY - 2023 SP - 128 UR - https://m2.mtmt.hu/api/publication/34736853 ID - 34736853 LA - Hungarian DB - MTMT ER - TY - JOUR AU - Juhász, Kinga AU - Varga, Bence AU - Bagi, Péter AU - Hell, Zoltán TI - Heterogeneous Catalytic Method for the Copper(II)-Catalysed Addition of H-Phosphinates and Secondary Phosphine Oxides to Phenylacetylene JF - CATALYSIS LETTERS J2 - CATAL LETT VL - 152 PY - 2022 IS - 4 SP - 1100 EP - 1108 PG - 9 SN - 1011-372X DO - 10.1007/s10562-021-03694-6 UR - https://m2.mtmt.hu/api/publication/32101347 ID - 32101347 N1 - Funding Agency and Grant Number: NRDI Fund (TKP2020 NC) under Ministry for Innovation and Technology [BME-NC]; New National Excellence Program of the Ministry of Human Capacities [uNKP-20-3-II-BME-282] Funding text: The research reported in this paper and carried out at BME has been supported by the NRDI Fund (TKP2020 NC, Grant No. BME-NC) based on the charter of bolster issued by the NRDI Office under the auspices of the Ministry for Innovation and Technology. B. V. acknowledges the financial support of the New National Excellence Program of the Ministry of Human Capacities (Grant number: uNKP-20-3-II-BME-282). LA - English DB - MTMT ER - TY - JOUR AU - Varga, Bence AU - Vincze, Daniella AU - Pető, Hajnalka AU - Buna, Levente AU - Pauló, János AU - Holczbauer, Tamás AU - Mátravölgyi, Béla AU - Hegedűs, László AU - Fogassy, Elemér AU - Keglevich, György AU - Bagi, Péter TI - Resolution of aryl-H-phosphinates applied in the synthesis of P-stereogenic compounds including a Brønsted acid NMR solvating agent JF - ORGANIC CHEMISTRY FRONTIERS J2 - ORG CHEM FRONT VL - 9 PY - 2022 IS - 10 SP - 2797 EP - 2807 PG - 11 SN - 2052-4110 DO - 10.1039/D2QO00241H UR - https://m2.mtmt.hu/api/publication/32776910 ID - 32776910 AB - An enantioseparation method for the preparation of P-stereogenicH-phosphinates was elaborated. In stereoselective reactions, various chiral P-stereogenic compounds were prepared and their applications as chiral NMR solvating agents were assessed. LA - English DB - MTMT ER - TY - JOUR AU - Popovics-Tóth, Nóra AU - Rávai, Bettina AU - Tajti, Ádám AU - Varga, Bence AU - Bagi, Péter AU - Perdih, Franc AU - Szabó, Pál Tamás AU - Hackler, Laszlo AU - Puskas, Laszlo G. AU - Bálint, Erika TI - Three-component synthesis, utilization and biological activity of phosphinoyl-functionalized isoindolinones JF - ORGANIC & BIOMOLECULAR CHEMISTRY J2 - ORG BIOMOL CHEM VL - 19 PY - 2021 IS - 40 SP - 8754 EP - 8760 PG - 7 SN - 1477-0520 DO - 10.1039/d1ob01610e UR - https://m2.mtmt.hu/api/publication/32346480 ID - 32346480 AB - A new method for the synthesis of 3-oxoisoindolin-1-ylphosphine oxides bearing same or different substituents on the phosphorus atom is described. The one-pot three-component reaction of 2-formylbenzoic acid, primary amines and achiral or P-stereogenic secondary phosphine oxides provided the target compounds under catalyst-free, mild conditions and for short reaction times. The deoxygenation of a 3-oxoisoindolin-1-ylphosphine oxide was also studied, and the phosphine obtained could be converted to a sulphide and to a platinum complex. The crystal structures of a selected phosphine oxide and the corresponding platinum species were investigated by X-ray diffraction analysis. The biological activity, such as in vitro cytotoxicity on different cell lines and antibacterial activity of the 3-oxoisoindolin-1-ylphosphine oxides was also investigated. Based on the IC50 values obtained, several derivatives showed moderate activity against the HL-60 cell line and two compounds containing 3,5-dimethylphenyl groups on the phosphorus atom showed promising activity against Bacillus subtilis bacteria. LA - English DB - MTMT ER - TY - JOUR AU - Varga, Bence AU - Szemesi, Péter AU - Nagy, Petra AU - Herbay, Réka AU - Holczbauer, Tamás AU - Fogassy, Elemér AU - Keglevich, György AU - Bagi, Péter TI - Enantioseparation of P-Stereogenic Secondary Phosphine Oxides and Their Stereospecific Transformation to Various Tertiary Phosphine Oxides and a Thiophosphinate JF - JOURNAL OF ORGANIC CHEMISTRY J2 - J ORG CHEM VL - 86 PY - 2021 IS - 21 SP - 14493 EP - 14507 PG - 15 SN - 0022-3263 DO - 10.1021/acs.joc.1c01364 UR - https://m2.mtmt.hu/api/publication/32487501 ID - 32487501 N1 - Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Müegyetem rkp. 3, Budapest, H-1111, Hungary Gedeon Richter Plc., Budapest, H-1475, Hungary Center for Structural Science, Chemical Crystallography Research Laboratory, Institute for Organic Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2, Budapest, H-1519, Hungary Export Date: 1 December 2021 CODEN: JOCEA Correspondence Address: Bagi, P.; Department of Organic Chemistry and Technology, Müegyetem rkp. 3, Hungary; email: bagi.peter@vbk.bme.hu LA - English DB - MTMT ER - TY - JOUR AU - Varga, Bence AU - Bagi, Péter TI - Preparation of Enantiomerically Enriched P-Stereogenic Dialkyl-Arylphosphine Oxides via Coordination Mediated Optical Resolution JF - SYMMETRY (BASEL) J2 - SYMMETRY-BASEL VL - 12 PY - 2020 IS - 2 PG - 13 SN - 2073-8994 DO - 10.3390/sym12020215 UR - https://m2.mtmt.hu/api/publication/31155527 ID - 31155527 N1 - Cited By :1 Export Date: 4 February 2021 Correspondence Address: Bagi, P.; Department of Organic Chemistry and Technology, Muegyetem rkp. 3, Hungary; email: pbagi@mail.bme.hu Funding details: Emberi Eroforrások Minisztériuma, EMMI Funding details: National Research, Development and Innovation Office Funding details: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, NKFIH, OTKA PD 116096 Funding text 1: Funding: This work was supported by the National Research, Development and Innovation Office—NKFIH (Grant No. OTKA PD 116096). Support of grant BME FIKP-BIO by Ministry of Human Capacities of Hungary (EMMI) is kindly acknowledged. Funding Agency and Grant Number: National Research, Development and Innovation Office-NKFIH [OTKA PD 116096]; Ministry of Human Capacities of Hungary (EMMI) Funding text: This work was supported by the National Research, Development and Innovation Office-NKFIH (Grant No. OTKA PD 116096). Support of grant BME FIKP-BIO by Ministry of Human Capacities of Hungary (EMMI) is kindly acknowledged. LA - English DB - MTMT ER - TY - JOUR AU - Varga, Bence AU - Herbay, Réka Gizella AU - Székely, György AU - Holczbauer, Tamás AU - Madarász, János AU - Mátravölgyi, Béla AU - Fogassy, Elemér AU - Keglevich, György AU - Bagi, Péter TI - Scalable Enantiomeric Separation of Dialkyl-arylphosphine oxides based on Host-Guest Complexation with TADDOL-derivatives, and their Recovery JF - EUROPEAN JOURNAL OF ORGANIC CHEMISTRY J2 - EUR J ORG CHEM VL - 2020 PY - 2020 IS - 12 SP - 1840 EP - 1852 PG - 13 SN - 1434-193X DO - 10.1002/ejoc.202000035 UR - https://m2.mtmt.hu/api/publication/31170711 ID - 31170711 N1 - Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3., Budapest, 1111, Hungary Advanced Membranes and Porous Materials Center, Physical Science and Engineering Division (PSE), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955–6900, Saudi Arabia Department of Chemical Engineering and Analytical Science, The University of Manchester, The Mill, Sackville Street, Manchester, M1 3BB, United Kingdom Chemical Crystallography Research Laboratory and Institute of Organic Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2., Budapest, 1519, Hungary Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Szent Gellért tér 4., Budapest, 1111, Hungary Cited By :1 Export Date: 4 February 2021 CODEN: EJOCF Correspondence Address: Bagi, P.; Department of Organic Chemistry and Technology, Műegyetem rkp. 3., Hungary; email: pbagi@mail.bme.hu Funding details: Hawaii Academy of Science, HAS Funding details: OTKA PD 128504 Funding details: King Abdullah University of Science and Technology, KAUST Funding details: National Research, Development and Innovation Office Funding details: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, NKFIH, OTKA PD 116096 Funding text 1: This work was supported by the National Research, Development and Innovation Office - NKFIH (Grant No. OTKA PD 116096). Tam?s Holczbauer is grateful for the support of the National Research, Development and Innovation Office-NKFIH (Grant No. OTKA PD 128504) and the J?nos Bolyai Research Scholarship of the HAS. Gy?rgy Sz?kely acknowledges the financial support from KAUST. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3., Budapest, 1111, Hungary Advanced Membranes and Porous Materials Center, Physical Science and Engineering Division (PSE), King Abdullah University of Science and Technology (KAUST), Thuwal, 23955–6900, Saudi Arabia Department of Chemical Engineering and Analytical Science, The University of Manchester, The Mill, Sackville Street, Manchester, M1 3BB, United Kingdom Chemical Crystallography Research Laboratory and Institute of Organic Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2., Budapest, 1519, Hungary Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Szent Gellért tér 4., Budapest, 1111, Hungary Cited By :1 Export Date: 30 May 2021 CODEN: EJOCF Correspondence Address: Bagi, P.; Department of Organic Chemistry and Technology, Műegyetem rkp. 3., Hungary; email: pbagi@mail.bme.hu Funding details: Hawaii Academy of Science, HAS Funding details: King Abdullah University of Science and Technology, KAUST Funding details: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, NKFIH, OTKA PD 116096 Funding details: National Research, Development and Innovation Office, OTKA PD 128504 Funding text 1: This work was supported by the National Research, Development and Innovation Office - NKFIH (Grant No. OTKA PD 116096). Tam?s Holczbauer is grateful for the support of the National Research, Development and Innovation Office-NKFIH (Grant No. OTKA PD 128504) and the J?nos Bolyai Research Scholarship of the HAS. Gy?rgy Sz?kely acknowledges the financial support from KAUST. AB - Several dialkyl‐arylphosphine oxides were prepared, and the enantioseparation of the corresponding racemates was elaborated with host–guest complexation using TADDOL‐derivatives. The crystallization conditions were optimized and two separate crystallization methods, one in organic solvent, and the other in water, were found to yield five examples of phosphine oxides with enantiomeric excess values higher than 94 %. A gram scale resolution was performed, and both enantiomers of the methyl‐phenyl‐propyl‐phosphine oxide were separated with (R,R)‐ or (S,S)‐spiro‐TADDOL. The intermolecular interactions responsible for the enantiomeric recognition between the chiral host and guest molecules were investigated by single‐crystal X‐ray diffractional structural determinations. The similarities in the structural patterns of a few diastereomeric crystals were checked by powder X‐ray diffraction, as well. Organic solvent nanofiltration (OSN) was used as a scalable technique for the decomposition of the corresponding phosphine oxide–spiro‐TADDOL molecular complexes, and for the recovery of the phosphine oxide enantiomers and resolving agents. LA - English DB - MTMT ER - TY - JOUR AU - Bagi, Péter AU - Herbay, Réka Gizella AU - Varga, Bence AU - Fersch, D. AU - Fogassy, Elemér AU - Keglevich, György TI - The preparation and application of optically active organophosphorus compounds JF - PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS J2 - PHOSPHOR SULFUR SIL REL ELEM VL - 194 PY - 2019 IS - 4-6 SP - 591 EP - 594 PG - 4 SN - 1042-6507 DO - 10.1080/10426507.2018.1547725 UR - https://m2.mtmt.hu/api/publication/30385213 ID - 30385213 N1 - Cited By :1 Export Date: 4 February 2021 CODEN: PSSLE Correspondence Address: Bagi, P.; Department of Organic Chemistry and Technology, Hungary; email: pbagi@mail.bme.hu Funding details: National Research, Development and Innovation Office Funding details: Nemzeti Kutatási Fejlesztési és Innovációs Hivatal, NKFIH, OTKA PD 116096 Funding text 1: National Research, Development and Innovation Office – NKFIH (Grant No. OTKA PD 116096). Funding Agency and Grant Number: National Research, Development and Innovation Office - NKFIH; OTKAOrszagos Tudomanyos Kutatasi Alapprogramok (OTKA) [PD 116096] Funding text: National Research, Development and Innovation Office - NKFIH (Grant No. OTKA PD 116096). LA - English DB - MTMT ER - TY - JOUR AU - Varga, Bence AU - Csizovszky, Anna AU - Bagi, Péter AU - Fogassy, Elemér AU - Keglevich, György TI - Resolution of acyclic phosphine oxides with TADDOL- and tartaric acid derivatives JF - PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS J2 - PHOSPHOR SULFUR SIL REL ELEM VL - 194 PY - 2019 IS - 4-6 SP - 556 EP - 557 PG - 2 SN - 1042-6507 DO - 10.1080/10426507.2018.1542405 UR - https://m2.mtmt.hu/api/publication/30649541 ID - 30649541 N1 - Export Date: 4 February 2021 CODEN: PSSLE Correspondence Address: Varga, B.; Department of Organic Chemistry and Technology, Hungary; email: varga.bence@mail.bme.hu Funding text 1: This work was supported by the National Research, Development and Innovation Office - NKFIH (Grant No. OTKA PD 116096). Funding Agency and Grant Number: National Research, Development and Innovation Office - NKFIH; OTKAOrszagos Tudomanyos Kutatasi Alapprogramok (OTKA) [PD 116096] Funding text: This work was supported by the National Research, Development and Innovation Office - NKFIH (Grant No. OTKA PD 116096). LA - English DB - MTMT ER -