Preparation and stereoselectivity of 1,3-dipolar cycloaddition ofD-glucose-derived nitrones to N-arylmaleimides |
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| Authors: | L Fišera U. A. R. Al-Timari P. Ertl N. Prónayová |
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| Affiliation: | (1) Department of Organic Chemistry, Slovak Technical University, 812 37 Bratislava, Slovakia;(2) Chemical Institute, Comenius University, 842 15 Bratislava, Slovakia;(3) Central Laboratory of Chemical Techniques, Slovak Technical University, 812 37 Bratislava, Slovakia |
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| Abstract: | Summary Nitrones2 derived fromD-glucose oxime and benzaldehydes without employing any protection of hydroxyl group were isolated in pure state. The 1,3-dipolar cycloaddition of2 to N-arylmaleimides gave predominantly theanti isoxazolidines3 and was rationalized byZ/E isomerization of N-glycosylnitrones2. The structure and steric configuration of the products have been assigned on the basis of1H- and13C-NMR spectroscopy. AM1 calculations of the nitrones and MM2 calculations of the adducts were performed.
Darstellung und Stereoselektivität der 1,3-dipolaren Cycloaddition vonD-Glucose-abgeleiteten Nitronen an N-Arylmaleimiden Zusammenfassung Die Nitrone2 wurden ausD-Glucoseoxim und Benzaldehyden ohne Schutz von Hydroxylgruppen in reinem Zustand erhalten. Die 1,3-dipolare Cycloaddition von2 an N-Arylmaleimiden ergab bevorzugt dieanti-Isoxazolidine3; dies wurde über eineZ/E-Isomerisierung der N-Glycosylnitrone2 rationalisiert. Struktur und Stereochemie wurden auf Basis von1H- und13C-NMR-Spektroskopie ermittelt. Außerdem wurden AM1-Berechnungen an den Nitronen und MM2-Rechnungen an den Addukten ausgeführt. |
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| Keywords: | 1,3-Dipolar cycloaddition of chiral nitrones D-Glucose-derived nitrones Stereoselectivity of 1,3-dipolar cycloaddition AM1 Calculations |
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