TY  - JOUR
AU  - Szakonyi, Zsolt
AU  - Balazs, A
AU  - Martinek, Tamás
AU  - Fülöp, Ferenc
TI  - Enantioselective addition of diethylzinc to aldehydes catalyzed by gamma-amino alcohols derived from (+)- and (-)-alpha-pinene
JF  - TETRAHEDRON-ASYMMETRY
J2  - TETRAHEDRON ASYMMETR
VL  - 17
PY  - 2006
IS  - 2
SP  - 199
EP  - 204
PG  - 6
SN  - 0957-4166
DO  - 10.1016/j.tetasy.2005.12.011
UR  - https://m2.mtmt.hu/api/publication/1012940
ID  - 1012940
N1  - CAplus AN 2006:128546 (Journal);
AB  - 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.
LA  - English
DB  - MTMT
ER  - 

TY  - JOUR
AU  - Szakonyi, Zsolt
AU  - Martinek, Tamás
AU  - Hetényi, Anasztázia
AU  - Fülöp, Ferenc
TI  - Synthesis and transformations of enantiomeric 1,2-disubstituted monoterpene derivatives
JF  - TETRAHEDRON-ASYMMETRY
J2  - TETRAHEDRON ASYMMETR
VL  - 11
PY  - 2000
IS  - 22
SP  - 4571
EP  - 4579
PG  - 9
SN  - 0957-4166
DO  - 10.1016/S0957-4166(00)00435-3
UR  - https://m2.mtmt.hu/api/publication/1014481
ID  - 1014481
N1  - Cited By :50            
            Export Date: 8 September 2023            
            CODEN: TASYE            
            Correspondence Address: Fülöp, F.; Inst. of Pharmaceutical Chemistry, POB 121, H-6701 Szeged, Hungary; email: fulop@pharma.szote.u-szeged.hu
AB  - 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.
LA  - English
DB  - MTMT
ER  - 

TY  - JOUR
AU  - Parkkinen, A
AU  - Fülöp, Ferenc
AU  - Pihlaja, K
TI  - FORMATION OF 1,3-PERHYDROBENZOXAZINES AND THEIR N-METHYL DERIVATIVES - A COMPARATIVE-STUDY
JF  - TETRAHEDRON
J2  - TETRAHEDRON
VL  - 47
PY  - 1991
IS  - 12-13
SP  - 2229
EP  - 2236
PG  - 8
SN  - 0040-4020
DO  - 10.1016/S0040-4020(01)96133-2
UR  - https://m2.mtmt.hu/api/publication/1016222
ID  - 1016222
AB  - 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.
LA  - English
DB  - MTMT
ER  -