caa a22 4500 469039299 CHVBK 20180323132806.0 cr unu---uuuuu 170328e19921101xx s 000 0 eng 10.1007/BF00810931 doi (NATIONALLICENCE)springer-10.1007/BF00810931 Preparation and stereoselectivity of 1,3-dipolar cycloaddition of C-glycosyl nitrones to N-arylmaleimides [Elektronische Daten] [Usama Al-Timari, Lubor Fišera, Peter Ertl, Igor Goljer, Nada Prónayová] Darstellung und Stereoselektivität der 1,3-dipolaren Cycloaddition von C-Glycosyl-Nitronen an N-Arylmaleimiden Summary: The cycloaddition of 3′-hydroxyglycosyl-N-methylnitrone (1) to N-arylmaleimides gave thesyn isoxazolidines6, whereas 3′-acetoxyglycosyl-N-methylnitrone (2) afforded theanti isoxazolidines8 and10. The formation of6 was rationalized by anexo attack, stereoelectronically preferred through the hydrogen bond between the pentose hydroxyl group and one of the carbonyl groups of N-arylmaleimide. The sterically preferredendo attack avoiding the repulsions between N-arylmaleimide and sugar moiety was proposed for addition of2. The structure and steric configuration of the products have been assigned on the basis of1H- and13C-NMR spectroscopy, mainly by nuclear Overhauser effect difference spectroscopy. AM1 calculations of the nitrones and MM2 calculations of the adducts were performed. Springer-Verlag, 1992 1,3-Dipolar cycloaddition of chiral nitrones nationallicence 3′-Hydroxy- and 3′-acetoxyglycosyl-N-methylnitrones nationallicence Stereoselectivity of 1,3-dipolar cycloaddition nationallicence AM1 calculations nationallicence Al-Timari Usama Department of Organic Chemistry, Slovak Technical University, CS-812 37, Bratislava, Czechoslovakia aut Fišera Lubor Department of Organic Chemistry, Slovak Technical University, CS-812 37, Bratislava, Czechoslovakia aut Ertl Peter Chemical Institute, Comenius University, CS-842 15, Bratislava, Czechoslovakia aut Goljer Igor Central Laboratory of Chemical Techniques, Slovak Technical University, CS-812 37, Bratislava, Czechoslovakia aut Prónayová Nada Central Laboratory of Chemical Techniques, Slovak Technical University, CS-812 37, Bratislava, Czechoslovakia aut Monatshefte für Chemie / Chemical Monthly Springer-Verlag 123/11(1992-11-01), 999-1013 0026-9247 123:11<999 1992 123 706 https://doi.org/10.1007/BF00810931 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF00810931 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Al-Timari Usama Department of Organic Chemistry, Slovak Technical University, CS-812 37, Bratislava, Czechoslovakia aut NATIONALLICENCE 700 1- Fišera Lubor Department of Organic Chemistry, Slovak Technical University, CS-812 37, Bratislava, Czechoslovakia aut NATIONALLICENCE 700 1- Ertl Peter Chemical Institute, Comenius University, CS-842 15, Bratislava, Czechoslovakia aut NATIONALLICENCE 700 1- Goljer Igor Central Laboratory of Chemical Techniques, Slovak Technical University, CS-812 37, Bratislava, Czechoslovakia aut NATIONALLICENCE 700 1- Prónayová Nada Central Laboratory of Chemical Techniques, Slovak Technical University, CS-812 37, Bratislava, Czechoslovakia aut NATIONALLICENCE 773 0- Monatshefte für Chemie / Chemical Monthly Springer-Verlag 123/11(1992-11-01), 999-1013 0026-9247 123:11<999 1992 123 706 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer