caa a22 4500 467949115 CHVBK 20180405193740.0 cr unu---uuuuu 170328e20050101xx s 000 0 eng 10.1007/s11144-005-0020-0 doi (NATIONALLICENCE)springer-10.1007/s11144-005-0020-0 (NATIONALLICENCE)springer-10.1007/s11144-005-0203-8 A novel asymmetric heterogeneous catalytic reaction: hydrogenation of ethyl 2-acetoxyacrylate on cinchonidine modified Pd and Pt catalyst [Elektronische Daten] [K. Szőri, György Szöllősi, K. Felföldi, Mihály Bartók] Summary: The transformations of a-ICN and b-ICN were studied in the presence of hydrogen in AcOH over Pt-alumina catalyst under the conditions of the enantioselective hydrogenation of EtPy (hydrogen pressure 1-30 bar, temperature 298-323 K). It was established that the quinoline skeleton of the alkaloids is hydrogenated even under mild experimental conditions, whereas hydrogenolysis of the oxazacycloalkane structure only takes place at hydrogen pressures exceeding 1 bar. ESI-MS-MS, HPLC-ESI-ion-trap MS and NMR made possible the identification of several hydrogenated cinchona alkaloid derivatives with so far unknown structures. According to these experimental results, the conformation of isocinchona alkaloids remains unchanged under the conditions of the enantioselective hydrogenation of activated ketones, making them suitable for utilization as chiral modifiers of well-defined conformation. Springer-Verlag/Akadémiai Kiadó, 2005 hydrogenation nationallicence platinum nationallicence palladium nationallicence Enantioselective nationallicence cinchonidine nationallicence enol esters nationallicence ethyl 2-acetoxyacrylate nationallicence Szőri K. Organic Catalysis Research Group of the Hungarian Academy of Sciences, Dóm tér 8, H-6720 Szeged, Hungary aut Szöllősi György Organic Catalysis Research Group, Department of Organic Chemistry, Organic Catalysis Research Group of the Hungarian Academy of Sciences, Dóm tér 8, H-6720 Szeged, Hungary, Szeged aut Felföldi K. Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary aut Bartók Mihály Department of Organic Chemistry, I: Organic Catalysis Research Group of the Hungarian Academy of Sciences; II: Department of Organic Chemistry, University of Szeged, I: Dóm tér 8, H-6720 Szeged, Hungary; II: Dóm tér 8, H-6720 Szeged, Hungary, H-6820, Szeged aut Reaction Kinetics and Catalysis Letters Kluwer Academic Publishers 84/1(2005-01-01), 151-156 0133-1736 84:1<151 2005 84 11144 https://doi.org/10.1007/s11144-005-0020-0 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s11144-005-0020-0 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Szőri K. Organic Catalysis Research Group of the Hungarian Academy of Sciences, Dóm tér 8, H-6720 Szeged, Hungary aut NATIONALLICENCE 700 1- Szöllősi György Organic Catalysis Research Group, Department of Organic Chemistry, Organic Catalysis Research Group of the Hungarian Academy of Sciences, Dóm tér 8, H-6720 Szeged, Hungary, Szeged aut NATIONALLICENCE 700 1- Felföldi K. Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary aut NATIONALLICENCE 700 1- Bartók Mihály Department of Organic Chemistry, I: Organic Catalysis Research Group of the Hungarian Academy of Sciences; II: Department of Organic Chemistry, University of Szeged, I: Dóm tér 8, H-6720 Szeged, Hungary; II: Dóm tér 8, H-6720 Szeged, Hungary, H-6820, Szeged aut NATIONALLICENCE 773 0- Reaction Kinetics and Catalysis Letters Kluwer Academic Publishers 84/1(2005-01-01), 151-156 0133-1736 84:1<151 2005 84 11144 NATIONALLICENCE 856 40 https://doi.org/10.1007/s11144-005-0203-8 text/html Onlinezugriff via DOI Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE NATIONALLICENCE NL-springer