Monatshefte für Chemie / Chemical Monthly

, Volume 124, Issue 10, pp 1019–1029 | Cite as

Preparation and stereoselectivity of 1,3-dipolar cycloaddition ofD-glucose-derived nitrones to N-arylmaleimides

  • L Fišera
  • U. A. R. Al-Timari
  • P. Ertl
  • N. Prónayová
Organische Chemie Und Biochemie

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.

Keywords

1,3-Dipolar cycloaddition of chiral nitrones D-Glucose-derived nitrones Stereoselectivity of 1,3-dipolar cycloaddition AM1 Calculations 

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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Copyright information

© Springer-Verlag 1993

Authors and Affiliations

  • L Fišera
    • 1
  • U. A. R. Al-Timari
    • 1
  • P. Ertl
    • 2
  • N. Prónayová
    • 3
  1. 1.Department of Organic ChemistrySlovak Technical UniversityBratislavaSlovakia
  2. 2.Chemical InstituteComenius UniversityBratislavaSlovakia
  3. 3.Central Laboratory of Chemical TechniquesSlovak Technical UniversityBratislavaSlovakia

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