@article{MTMT:1013238, title = {Advanced procedure for the enzymatic ring opening of unsaturated alicyclic beta-lactams}, url = {https://m2.mtmt.hu/api/publication/1013238}, author = {Forró, Enikő and Fülöp, Ferenc}, doi = {10.1016/j.tetasy.2004.05.029}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {15}, unique-id = {1013238}, issn = {0957-4166}, abstract = {Enantiopure beta-amino acids 1a-4a and beta-lactams 1b-4b were prepared simultaneously through the lipolase-catalysed enantioselective ring opening of unsaturated racemic beta-lactams (+/-)-1-(+/-)-4. High enantioselectivities (E >200) were observed when the reactions were performed with 1 equiv of water in iPr(2)O at 70degreesC. The resolved (1R,2S)-amino acids (yield greater than or equal to 45%) and (1S,5R)-, (1S,6R)- and (1S,8R)-lactams (yield greater than or equal to47%) could be easily separated. The ring opening of lactam enantiomers 1b-4b with 18% HCl afforded the corresponding beta-amino acid hydrochlorides 1c(.)HCl-4c(.)HCl (ee >95%). (C) 2004 Elsevier Ltd. All rights reserved.}, year = {2004}, eissn = {1362-511X}, pages = {2875-2880}, orcid-numbers = {Forró, Enikő/0000-0001-6796-3889; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:2326718, title = {Synthesis of enantiopure 1,4-ethyl- and 1,4-ethylene-bridged cispentacin by lipase-catalyzed enantioselective ring opening of beta-lactams}, url = {https://m2.mtmt.hu/api/publication/2326718}, author = {Forró, Enikő and Fülöp, Ferenc}, doi = {10.1016/j.tetasy.2003.12.034}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {15}, unique-id = {2326718}, issn = {0957-4166}, abstract = {1, 4-Ethyl- and 1,4-ethylene-bridged cispentacin enantiomers 1a, 1c and 2a, 2c were prepared through the lipase-catalyzed enantioselective ring opening of racemic exo-3-azatricyclo[4.2.1.0(2.5)]nonan-4-one, (+/-)-1, and exo-3-azatricyclo[4.2.1.0(2.5)]non-7-en-4-one, (+/-)-2. High enantioselectivity (E >200) was observed when the Lipolase-catalyzed reactions were performed with 1 equiv of H2O in diisopropyl ether at 70degreesC. The resolved beta-amino acids 1a and 2a (yield,46%) and beta-lactams 1b and 2b (yield greater than or equal to40%) could be easily separated. The ring opening of lactam enantiomers with 18% HCl afforded the corresponding beta-amino acid hydrochloride enantiomers (ee greater than or equal to98%). (C) 2004 Elsevier Ltd. All rights reserved.}, keywords = {AMINO-ACIDS; ENANTIOMERS; ALPHA-AMINO}, year = {2004}, eissn = {1362-511X}, pages = {573-575}, orcid-numbers = {Forró, Enikő/0000-0001-6796-3889; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1013236, title = {A new strategy to produce beta-peptides: Use of alicyclic beta-lactams}, url = {https://m2.mtmt.hu/api/publication/1013236}, author = {Fülöp, Ferenc and Forró, Enikő and Tóth, Gábor}, doi = {10.1021/ol048356t}, journal-iso = {ORG LETT}, journal = {ORGANIC LETTERS}, volume = {6}, unique-id = {1013236}, issn = {1523-7060}, abstract = {On p-methylbenzhydrylamine (MBHA) resin, by means of t-Boc chemistry, several tetrapeptides (H-Ala-ACXC-Ala-Gly-NH2) containing cyclic beta-amino acid units were prepared. These units were introduced into the growing peptide chain by using Boc-protected beta-lactams with KCN as catalyst in DMF. The method was applicable for both racemic and enantiomeric beta-lactams.}, keywords = {ARTICLE; CATALYSIS; high performance liquid chromatography; amino acid sequence; chemical structure; ENANTIOSELECTIVITY; solid; beta lactam derivative}, year = {2004}, eissn = {1523-7052}, pages = {4239-4241}, orcid-numbers = {Fülöp, Ferenc/0000-0003-1066-5287; Forró, Enikő/0000-0001-6796-3889; Tóth, Gábor/0000-0002-3604-4385} } @article{MTMT:118394, title = {Chemoenzimatic preparation of enantiopure homoadamantyl beta-amino acid and beta-lactam derivatives}, url = {https://m2.mtmt.hu/api/publication/118394}, author = {Gyarmati, Zsuzsanna and Liljeblad, A and Argay, Gyula and Kálmán, A and Bernáth, Gábor and Kanerva, L}, doi = {10.1002/adsc.200303205}, journal-iso = {ADV SYNTH CATAL}, journal = {ADVANCED SYNTHESIS & CATALYSIS}, volume = {346}, unique-id = {118394}, issn = {1615-4150}, year = {2004}, eissn = {1615-4169}, pages = {566-572} } @article{MTMT:1013249, title = {Synthesis of the enantiomers and N-protected derivatives of 3-amino-3-(4-cyanophenyl)propanoic acid}, url = {https://m2.mtmt.hu/api/publication/1013249}, author = {Solymar, M and Kanerva, L T and Fülöp, Ferenc}, doi = {10.1016/j.tetasy.2004.05.012}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {15}, unique-id = {1013249}, issn = {0957-4166}, abstract = {Racemic ethyl 3-amino-3-(4-cyanophenyl)propanoate was synthesized and the enantiomers separated through enantioselective N-acylation by Candida antarctica lipase A (CAL-A) in neat butyl butanoate. The free amino acid enantiomers were transformed to the Boc and Fmoc-protected derivatives. (C) 2004 Elsevier Ltd. All rights reserved.}, year = {2004}, eissn = {1362-511X}, pages = {1893-1897}, orcid-numbers = {Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1013530, title = {Lipase-catalyzed enantioselective ring opening of unactivated alicyclic-fused beta-lactams in an organic solvent}, url = {https://m2.mtmt.hu/api/publication/1013530}, author = {Forró, Enikő and Fülöp, Ferenc}, doi = {10.1021/ol034096o}, journal-iso = {ORG LETT}, journal = {ORGANIC LETTERS}, volume = {5}, unique-id = {1013530}, issn = {1523-7060}, abstract = {A highly efficient and very simple method was developed for the synthesis of enantiopure beta-amino acids (e.g. cispentacin) and beta-lactams through the enzyme-catalyzed enantioselective ring opening of unactivated alicyclic, beta-lactams in organic media. High enantioselectivity (E > 200) was observed when the Lipolase flipase B from Candida antarctica)-catalyzed reactions were performed with H2O (1 equiv) in dilsopropyl ether at 60 degreesC. The resolved products, obtained in good chemical yield (36-47%), could be easily separated.}, year = {2003}, eissn = {1523-7052}, pages = {1209-1212}, orcid-numbers = {Forró, Enikő/0000-0001-6796-3889; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:118395, title = {Lipase-catalyzed kinetic resolution of 7-, 8- and 12-membered alicyclic beta-amino esters and N-hydroxymethyl-beta-lactam enantiomers}, url = {https://m2.mtmt.hu/api/publication/118395}, author = {Gyarmati, Zsuzsanna and Liljeblad, A and Rintola, M and Bernáth, Gábor and Kanerva, L}, doi = {10.1016/j.tetasy.2003.08.028}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {14}, unique-id = {118395}, issn = {0957-4166}, year = {2003}, eissn = {1362-511X}, pages = {3805-3814} } @article{MTMT:1013524, title = {Molecular basis for the enantioselective ring opening of beta-lactams catalyzed by Candida antarctica lipase B}, url = {https://m2.mtmt.hu/api/publication/1013524}, author = {Park, S and Forró, Enikő and Grewal, H and Fülöp, Ferenc and Kazlauskas, R I}, doi = {10.1002/adsc.200303069}, journal-iso = {ADV SYNTH CATAL}, journal = {ADVANCED SYNTHESIS & CATALYSIS}, volume = {345}, unique-id = {1013524}, issn = {1615-4150}, abstract = {Lipase B from Candida antarctica (CAL-B) catalyzes the slow, but highly enantioselective (E >200), ring-opening alcoholysis of two bicyclic and two 4-aryl-substituted beta-lactams. Surprisingly, the rate of the reaction varies with the nature of the alcohols and was fastest with either enantiomer of 2-octanol. A 0.5-g scale reaction with 2-octanol as the nucleophile in diisopropyl ether at 60degreesC yielded the unreacted beta-lactam in 39-46% yield (maximum yield is 50%) with greater than or equal to96% ee. The product beta-amino acid esters reacted further by polymerization (not isolated or characterized) or by hydrolysis due to small amounts of water in the reaction mixture yielding beta-amino acids (7-11% yield, greater than or equal to96% ee). The favored enantiomer of all four beta-lactams had similar 3-D orientation of substituents, as did most previously reported beta-lactams and beta-lactones in similar ring-opening reactions. Computer modeling of the ring opening of 4-phenylazetidin-2-one suggests that the reaction proceeds via an unusual substrate-assisted transition state, where the substrate alcohol bridges between the catalytic histidine and the nitrogen of the beta-lactam. Computer modeling also suggested that the molecular basis for the high enantioselectivity is a severe steric clash between Ile189 in CAL-B and the phenyl substituent on the slow-reacting enantiomer of the beta-lactam.}, year = {2003}, eissn = {1615-4169}, pages = {986-995}, orcid-numbers = {Forró, Enikő/0000-0001-6796-3889; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1013823, title = {Structural effects on chemo- and enantio-selectivity of Candida antarctica lipase B - Resolution of beta-amino esters}, url = {https://m2.mtmt.hu/api/publication/1013823}, author = {Gedey, S and Liljeblad, A and Lázár, László and Fülöp, Ferenc and Kanerva, L T}, doi = {10.1139/V02-015}, journal-iso = {CAN J CHEM}, journal = {CANADIAN JOURNAL OF CHEMISTRY}, volume = {80}, unique-id = {1013823}, issn = {0008-4042}, abstract = {The Candida antarctica lipase B-catalyzed reactions of five beta-amino esters with neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied, as were the reactions of the same beta-amino esters and their N-butanamides with neat butanol. The possibility for sequential resolution, where the amino and ester functions of the substrate both react with an achiral butanoate, became less likely with increasing size of the substrate from ethyl 3-aminobutanoate (1a) to pentanoate (1b) or larger. On the other hand, the alcoholyses of N-acylated beta-amino esters successfully proceeded in butanol with E > 100. Gram-scale resolution of the N-butanoylated la was performed to demonstrate the usefulness of the method.}, year = {2002}, eissn = {1480-3291}, pages = {565-570}, orcid-numbers = {Lázár, László/0000-0002-2135-8496; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1013817, title = {Candida antarctica lipase A - a powerful catalyst for the resolution of heteroaromatic beta-amino esters}, url = {https://m2.mtmt.hu/api/publication/1013817}, author = {Solymar, M and Fülöp, Ferenc and Kanerva, L T}, doi = {10.1016/S0957-4166(02)00637-7}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {13}, unique-id = {1013817}, issn = {0957-4166}, abstract = {Enantioselective acylations of 3-amino-3-beteroarylpropanoates (ArCH(NH2)CH2CO2Et; Ar = 2- or 3-thienyl or -furyl) were performed in the presence of Candida antarctica lipase A. As a result of the excellent chemo- and enantioselectivities (E > 100), gram-scale resolutions were carried out in ethyl butanoate. The hydrochloride salts of the unreacted R substrates and the butanamides of the reactive S enantiomers were thus prepared. (C) 2002 Elsevier Science Ltd. All rights reserved.}, year = {2002}, eissn = {1362-511X}, pages = {2383-2388}, orcid-numbers = {Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1013820, title = {Lipase-catalysed kinetic resolution in organic solvents: an approach to enantiopure alpha-methyl-beta-alanine esters}, url = {https://m2.mtmt.hu/api/publication/1013820}, author = {Solymar, M and Liljeblad, A and Lázár, László and Fülöp, Ferenc and Kanerva, L T}, doi = {10.1016/S0957-4166(02)00478-0}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {13}, unique-id = {1013820}, issn = {0957-4166}, abstract = {The Candida antarctica lipase A (CAL-A) and B (CAL-B)-catalysed resolutions of alpha-methyl-beta-alanine ethyl ester 1 wit neat ethyl and butyl butanoates and with 2,12-trifluoroethyl butanoate in organic solvents Were Studied, as were the alcoholyses in neat butanol and with methanol (0.8 M) in diisopropyl ether. The two enzymes, which display opposite (S for CAL-A and R for CAL-B) and low enantioselectivities (E=7-10), allowed the preparation of the two enantiomers in a two-step resolution protocol. The R enantiomer (ee=97%) was first separated as its Boc-protected derivative front the CAL-A-catalysed resolution mixture of (R)-1 and the enantiomerically enriched N-butanoylated counterpart. The enantiopurification of the latter gave the S enantiomer (ec=96%)) in the following CAL-B-catalysed 'interesterification' in butyl butanoate. (C) 2002 Elsevier Science Ltd. All rights reserved.}, year = {2002}, eissn = {1362-511X}, pages = {1923-1928}, orcid-numbers = {Lázár, László/0000-0002-2135-8496; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1013900, title = {Preparation of (1R,8S)- and (1S,8R)-9-azabicyclo[6.2.0]dec-4-en-10-one: potential starting compounds for the synthesis of anatoxin-a}, url = {https://m2.mtmt.hu/api/publication/1013900}, author = {Forró, Enikő and Arva, J and Fülöp, Ferenc}, doi = {10.1016/S0957-4166(01)00100-8}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {12}, unique-id = {1013900}, issn = {0957-4166}, abstract = {9-Azabicyclo[6.2.0]dec-4-en-10-one (+/-)-2, obtained from cyclooctadiene by addition of chlorosulfonyl isocyanate, was N-hydroxymethylated to (+/-)-3 and then resolved by lipase-catalysed asymmetric acylation of the primary OH group at the (S)-stereogenic centre. High enantioselectivity (E=94) was observed when lipase PS and vinyl butyrate were used in di-iso-propyl ether at -15 degreesC, resulting in the enantiomerically enriched ester 3a and alcohol 3b (e.e. greater than or equal to 92%). Treatment of 3a and 3b with NH4OH/MeOH afforded the corresponding beta -lactams (1R,8S)-2a and (1S,8R)-2b (e.e. greater than or equal to 93%), potential starting compounds in anatoxin-a synthesis. The ring opening of lactams (+/-)-2, (+/-)-7, 3a and 3b, followed by reduction, resulted in racemic 4-6 and 8 and enantiomeric 4a, 3b, 5a and 5b eight-membered cyclic beta -amino acid derivatives. (C) 2001 Published by Elsevier Science Ltd.}, year = {2001}, eissn = {1362-511X}, pages = {643-649}, orcid-numbers = {Forró, Enikő/0000-0001-6796-3889; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1013890, title = {Synthesis of 4-aryl-substituted beta-lactam enantiomers by enzyme-catalyzed kinetic resolution}, url = {https://m2.mtmt.hu/api/publication/1013890}, author = {Forró, Enikő and Fülöp, Ferenc}, doi = {10.1016/S0957-4166(01)00388-3}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {12}, unique-id = {1013890}, issn = {0957-4166}, abstract = {Enantiopure 4-phenyl- and 4-(p-tolyl)-2-azetidinones 3a, 3b, 4a and 4b (with e.e.s of greater than or equal to 96%) were prepared through lipase-catalyzed asymmetric butyrylation of the primary OH group of N-hydroxymethylated beta -lactams (+/-)-5 and (+/-)-6 at the (R)-stereogenic centre or by lipase-catalyzed asymmetric debutyrylation of O-butyryloxymethyl-2-azetidinones (+/-)-7 and (+/-)-8 at the (R)-stereogenic centre. The ring-opening of lactams 5a. 5b, 6b and 8a with HCl/EtOH afforded the corresponding P-amino ester enantiomers 9a, 9b, 10a and 10b with e.e.s or greater than or equal to 92%, (C) 2001 Elsevier Science Ltd. All rights reserved.}, year = {2001}, eissn = {1362-511X}, pages = {2351-2358}, orcid-numbers = {Forró, Enikő/0000-0001-6796-3889; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1013895, title = {The chemistry of 2-aminocycloalkanecarboxylic acids}, url = {https://m2.mtmt.hu/api/publication/1013895}, author = {Fülöp, Ferenc}, doi = {10.1021/cr000456z}, journal-iso = {CHEM REV}, journal = {CHEMICAL REVIEWS}, volume = {101}, unique-id = {1013895}, issn = {0009-2665}, year = {2001}, eissn = {1520-6890}, pages = {2181-2204}, orcid-numbers = {Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1013902, title = {Preparation of highly enantiopure beta-amino esters by Candida antarctica lipase A}, url = {https://m2.mtmt.hu/api/publication/1013902}, author = {Gedey, S and Liljeblad, A and Lázár, László and Fülöp, Ferenc and Kanerva, L T}, doi = {10.1016/S0957-4166(01)00002-7}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {12}, unique-id = {1013902}, issn = {0957-4166}, abstract = {The enantioselectivities for the reactions of aliphatic beta -substituted beta -amino esters [RCH(NH2)CH2CO2Et with R = Me, Et, n-Pr, i-Pr, CHEt2, cyclohexyl and Ph] with butyl butanoate in neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied in the presence of Candida antarctica lipase A. Enantioselectivities ranging from good (E=70-100) to excellent (E>100) were commonly observed, allowing gram-scale resolution of the substrates. (C) 2001 Elsevier Science Ltd. All rights reserved.}, year = {2001}, eissn = {1362-511X}, pages = {105-110}, orcid-numbers = {Lázár, László/0000-0002-2135-8496; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1013899, title = {Enzymatic resolution of bicyclic 1,3-amino alcohols in organic media}, url = {https://m2.mtmt.hu/api/publication/1013899}, author = {Kaman, J and van Der, Eycken J and Péter, Antal and Fülöp, Ferenc}, doi = {10.1016/S0957-4166(01)00093-3}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {12}, unique-id = {1013899}, issn = {0957-4166}, abstract = {N-Protected racemic di-exo- and di-endo-3-aminobicyclo[2.2.1]heptane-2-methanols and di-exo- and di-endo-3-aminobicyclo[2.2.1]hept-5-ene-2-methanols were resolved through lipase-catalysed O-acylation, using vinyl butyrate in organic solvents. Of the lipases screened most showed a preference for the (2S)-enantiomer. (C) 2001 Published by Elsevier Science Ltd.}, year = {2001}, eissn = {1362-511X}, pages = {625-631}, orcid-numbers = {Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1014471, title = {Synthesis of all four enantiomers of 1-aminoindane-2-carboxylic acid, a new cispentacin benzologue}, url = {https://m2.mtmt.hu/api/publication/1014471}, author = {Fülöp, Ferenc and Palkó, Márta and Kaman, J and Lázár, László and Sillanpaa, R}, doi = {10.1016/S0957-4166(00)00375-X}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {11}, unique-id = {1014471}, issn = {0957-4166}, abstract = {Racemic cis- and trans-1-aminoindane-2-carboxylic acids (3 and 5) were prepared from indene by chlorosulphonyl isocyanate addition followed by ring opening and isomerisation. The intermediate racemic hydroxymethylated beta -lactam 6 was resolved through the lipase-catalysed asymmetric acylation of the primary hydroxy group at the (R)-stereogenic centre. High enantioselectivities (E>200) were observed when the enzymatic reactions were performed with lipase AK or lipase PS as catalyst and vinyl acetate or vinyl butyrate as acyl donor. The hydrolysis and isomerisation resulted in all four enantiomers (9, 11, 13 and 14) of 1-aminoindane-2-carboxylic acid, a new benzologue of cispentacin. (C) 2000 Elsevier Science Ltd. All rights reserved.}, year = {2000}, eissn = {1362-511X}, pages = {4179-4187}, orcid-numbers = {Fülöp, Ferenc/0000-0003-1066-5287; Palkó, Márta/0000-0002-8265-7377; Lázár, László/0000-0002-2135-8496} } @inbook{MTMT:1014519, title = {The chemistry of 2-aminocyclopentanecarboxylic acid}, url = {https://m2.mtmt.hu/api/publication/1014519}, author = {Fülöp, Ferenc}, booktitle = {Studies in Natural Products Chemistry: Bioactive Natural Products (Part C)}, doi = {10.1016/S1572-5995(00)80028-9}, unique-id = {1014519}, year = {2000}, pages = {273-306}, orcid-numbers = {Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1014473, title = {Enzymatic resolution of alicyclic beta-lactams}, url = {https://m2.mtmt.hu/api/publication/1014473}, author = {Kaman, J and Forró, Enikő and Fülöp, Ferenc}, doi = {10.1016/S0957-4166(00)00070-7}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {11}, unique-id = {1014473}, issn = {0957-4166}, abstract = {Racemates of N-hydroxymethylated beta-lactams 4-6 were resolved through the lipase-catalyzed asymmetric acylation of the primary hydroxy group at the 6S stereogenic centre. High enantioselectivity (E > 200) was observed when the enzymatic reactions were performed in acetone with lipase PS as catalyst and vinyl butyrate as acyl donor. The hydrolysis of the enantiomeric azetidinones 4a-6a and 4b-6b resulted in the enantiomerically pure alicyclic beta-amino acids 4c-6c and 4d-6d. When the less reactive enantiomers 4b-6b were treated with NH4OH/MeOH, enantiomerically pure beta-lactams 4e-6e were formed. (C) 2000 Elsevier Science Ltd. All rights reserved.}, year = {2000}, eissn = {1362-511X}, pages = {1593-1600}, orcid-numbers = {Forró, Enikő/0000-0001-6796-3889; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1014481, title = {Synthesis and transformations of enantiomeric 1,2-disubstituted monoterpene derivatives}, url = {https://m2.mtmt.hu/api/publication/1014481}, author = {Szakonyi, Zsolt and Martinek, Tamás and Hetényi, Anasztázia and Fülöp, Ferenc}, doi = {10.1016/S0957-4166(00)00435-3}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {11}, unique-id = {1014481}, issn = {0957-4166}, abstract = {Regio- and stereospecific addition of chlorosulfonyl isocyanate to (+)- and (-)-alpha -pinene I resulted in enantiomerically pure beta -lactams 2, which were converted to enantiomeric beta -amino esters 3 and 1,3-amino alcohols 4 and 6 with ee >99%. The resulting 1,3-difunctional compounds 3, 4 and 6 were transformed to fused saturated 1,3-heterocycles such as tetrahydro-1,3- oxazines 7 and 9, 2,4-pyrimidinedione 11 and 2-thioxopyrimidin- 4-one 13 enantiomers. (C) 2000 Elsevier Science Ltd. All rights reserved.}, year = {2000}, eissn = {1362-511X}, pages = {4571-4579}, orcid-numbers = {Szakonyi, Zsolt/0000-0003-2432-8409; Martinek, Tamás/0000-0003-3168-8066; Hetényi, Anasztázia/0000-0001-8080-6992; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:1014573, title = {Sequential resolution of ethyl 3-aminobutyrate with carboxylic acid esters by Candida antarctica lipase B}, url = {https://m2.mtmt.hu/api/publication/1014573}, author = {Gedey, S and Liljeblad, A and Fülöp, Ferenc and Kanerva, L T}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {10}, unique-id = {1014573}, issn = {0957-4166}, abstract = {The reactions of ethyl 3-aminobutyrate 1 with carboxylic acid esters, catalyzed by lipases from Candida antarctica, Pseudomonas cepacia and Pseudomonas fluorescens, have been studied. The reactions take place on the amino and ester functions of the substrate provided that the alkyl group of the achiral ester differs from ethyl. This property has been exploited for the Candida antarctica lipase B-catalyzed resolution of 1 in butyl butyrate, leading to the unreacted enantiomer (S)-1 and butyl 3-aminobutyrate, and to the butanamide of butyl (R)-3-aminobutyrate, (C) 1999 Elsevier Science Ltd. All rights reserved.}, year = {1999}, eissn = {1362-511X}, pages = {2573-2581}, orcid-numbers = {Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:27976, title = {A simple synthesis of beta-alkyl-substituted beta-amino acids}, url = {https://m2.mtmt.hu/api/publication/27976}, author = {Lázár, László and Martinek, Tamás and Bernáth, Gábor and Fülöp, Ferenc}, doi = {10.1080/00397919808005714}, journal-iso = {SYNTHETIC COMMUN}, journal = {SYNTHETIC COMMUNICATIONS}, volume = {28}, unique-id = {27976}, issn = {0039-7911}, abstract = {By the condensation of branched-chain aliphatic or alicyclic aldehydes with malonic acid in the presence of ammonium acetate, beta-alkyl-substituted beta-amino acids were prepared.}, year = {1998}, eissn = {1532-2432}, pages = {219-224}, orcid-numbers = {Lázár, László/0000-0002-2135-8496; Martinek, Tamás/0000-0003-3168-8066; Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:27972, title = {Enzymatic resolution of alicyclic 1,3-amino alcohols in organic media}, url = {https://m2.mtmt.hu/api/publication/27972}, author = {Péter, Mária and van Der, Eycken J and Bernáth, Gábor and Fülöp, Ferenc}, doi = {10.1016/S0957-4166(98)00236-5}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {9}, unique-id = {27972}, issn = {0957-4166}, abstract = {Racemic cis- and trans-2-aminocyclohexane-1-methanol and cis- and trans-2-amino-4-cyclohexene-1-methanol were resolved via lipase-catalysed O-acylation of their Z derivatives, using vinyl butyrate in different ether solvents. In accordance with the empirical rule, most of the screened lipases preferred the 1S enantiomer. (C) 1998 Elsevier Science Ltd. All rights reserved.}, year = {1998}, eissn = {1362-511X}, pages = {2339-2347}, orcid-numbers = {Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:27988, title = {Biocatalysis for the preparation of optically active beta- lactam precursors of amino acids}, url = {https://m2.mtmt.hu/api/publication/27988}, author = {Csomós, Péter and Kanerva, LT and Bernáth, Gábor and Fülöp, Ferenc}, doi = {10.1016/0957-4166(96)00214-5}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {7}, unique-id = {27988}, issn = {0957-4166}, abstract = {Enantioselective acylation of N-hydroxymethylated beta-lactams in the presence of Pseudomonas sp. lipase afforded optically active precursors for the preparation of (1R,2S)- and (1S,2R)-2-aminocyclopentane- and (1R,2S,3R,4S)- and (1S,2R,3S,4R)-3-aminobicyclo[2.2.1]heptanecarboxylic acids. Due to the high enantioselectivity (E = 90 and 62) and in order to minimize the enzymatic hydrolysis of the acylated products back to the starting alcohol, the reactions were performed in acetone. Copyright (C) 1996 Elsevier Science Ltd}, year = {1996}, eissn = {1362-511X}, pages = {1789-1796}, orcid-numbers = {Fülöp, Ferenc/0000-0003-1066-5287} } @article{MTMT:27987, title = {Approach to highly enantiopure beta-amino acid esters by using lipase catalysis in organic media}, url = {https://m2.mtmt.hu/api/publication/27987}, author = {Kanerva, LT and Csomós, Péter and Sundholm, O and Bernáth, Gábor and Fülöp, Ferenc}, doi = {10.1016/0957-4166(96)00204-2}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {7}, unique-id = {27987}, issn = {0957-4166}, abstract = {Ethyl esters often alicyclic beta-aminocarboxylic acids were resolved by lipase catalysis in organic solvents. The resolution was based on acylation of the amino group at the R-stereogenic centre with various 2,2,2-trifluoroethyl esters. An increase in the hydrophobic nature of the acyl donor enhanced the enantioselectivity and reactivity in the case of lipase SP 526 from Candida antarctica, while the opposite effect was observed with lipase PS from Pseudomonas cepacia. An unexceptional enantioselectivity enhancement was observed when 2,2,2-trifluoroethyl chloroacetate was used in the case oflipase PS catalysis. Copyright (C) 1996 Elsevier Science Ltd}, year = {1996}, eissn = {1362-511X}, pages = {1705-1716}, orcid-numbers = {Fülöp, Ferenc/0000-0003-1066-5287} }