1,3-Dipolar Cycloaddition of D-Xylose Derived Nitrone with Methyl Acrylate and its Utilization in Synthesis of Chiral Polyhydroxylated Pyrrolidinones and Pyrrolidines
Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Radlinského 9, 81237 Bratislava, Slovak Republic
a Institute of Analytical Chemistry, Slovak University of Technology, Radlinského 9, 81237 Bratislava, Slovak Republic
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Abstract: The cycloaddition of the chiral nitrone IV derived from D-xylose with methyl acrylate proceeded with very good diastereoselectivity for the anti-trans isoxazolidine Va. Its subsequent transformations to novel chiral polyhydroxylated pyrrolidinones and pyrrolidines are described. The results show that the method has potential use in the preparation of pyrrolidinones and pyrrolidines containing carbohydrate residues.
Keywords: chiral nitrones, pyrrolidines, cycloadditions
Full paper in Portable Document Format: acs_0030.pdf
Acta Chimica Slovaca, Vol. 1, No. 1, 2008, pp. 350—360