@article{MTMT:1012940, title = {Enantioselective addition of diethylzinc to aldehydes catalyzed by gamma-amino alcohols derived from (+)- and (-)-alpha-pinene}, url = {https://m2.mtmt.hu/api/publication/1012940}, author = {Szakonyi, Zsolt and Balazs, A and Martinek, Tamás and Fülöp, Ferenc}, doi = {10.1016/j.tetasy.2005.12.011}, journal-iso = {TETRAHEDRON ASYMMETR}, journal = {TETRAHEDRON-ASYMMETRY}, volume = {17}, unique-id = {1012940}, issn = {0957-4166}, abstract = {Primary, secondary and tertiary gamma-amino alcohols 4, 5, 7 and 9 and 1,3-diamine 6 were synthesized from (+)- and (-)-alpha-pinene 1 via chiral N-Boc beta-amino ester 3a and carboxamide 3b. The amino alcohols and diamine obtained were applied as chiral catalysts in the enantioselective addition of diethylzinc to aromatic aldehydes, resulting in chiral 1-aryl-1-propanols. The first evidence of the substituent-dependent enantioselectivity of 1,3-amino alcohol catalysts was observed, and the phenomenon interpreted by using molecular modelling at the ab initio level. (c) 2005 Elsevier Ltd. All rights reserved.}, year = {2006}, eissn = {1362-511X}, pages = {199-204}, orcid-numbers = {Szakonyi, Zsolt/0000-0003-2432-8409; Martinek, Tamás/0000-0003-3168-8066; 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:1016222, title = {FORMATION OF 1,3-PERHYDROBENZOXAZINES AND THEIR N-METHYL DERIVATIVES - A COMPARATIVE-STUDY}, url = {https://m2.mtmt.hu/api/publication/1016222}, author = {Parkkinen, A and Fülöp, Ferenc and Pihlaja, K}, doi = {10.1016/S0040-4020(01)96133-2}, journal-iso = {TETRAHEDRON}, journal = {TETRAHEDRON}, volume = {47}, unique-id = {1016222}, issn = {0040-4020}, abstract = {The formation of perhydro-1,3-oxazine derivatives (3) through the cyclization reaction of p-nitrobenzaldehyde with cis- (1) and trans-2-aminomethyl-1-cyclohexanol (2) or with their N-methyl derivatives (1m and 2m) were studied by H-1 NMR spectroscopy in CDCl3. The reactions with 1 and 2 proceeded via open-chain intermediates whereas those with 1m and 2m showed no signs of these intermediates. The cyclization reactions of the N-methyl substituted cyclohexanols (1m and 2m) were much faster than those of the corresponding hydroxymethylcyclohexylamines studied earlier. The cyclization of 1 was kinetically controlled but in much lesser extent than the corresponding reaction with cis-2-hydroxymethyl-1-cyclohexylamine. These results confirmed that the cyclization reactions of p-nitrobenzaldehyde with 2-aminomethyl-1-cyclohexanols and their N-methyl derivatives parallel to those with 2-hydroxymethyl-1-cyclohexylamines and their N-methyl derivatives are not usually diastereospecific.}, year = {1991}, eissn = {1464-5416}, pages = {2229-2236}, orcid-numbers = {Fülöp, Ferenc/0000-0003-1066-5287} }