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Synlett 2001; 2001(12): 1862-1865
DOI: 10.1055/s-2001-18782
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Stereoselectivity of 1,3-Dipolar Cycloadditions of d-Erythrose and d-Threose Derived Nitrones with Methyl Acrylate

Juraj Kubáň* , Andrej Kolarovič, Lubor Fišera, Volker Jäger, Otakar Humpa, Nada Prónayová, Peter Ertl
  • *Department of Organic Chemistry, Slovak University of Technology, SK-812 37 Bratislava, Slovak Republic; E-mail: fisera@cvt.stuba.sk
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Publication Date:
04 December 2001 (online)

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1,3-Dipolar cycloadditions between the d-erythrose and d-threose derived nitrones and methyl acrylate proceed in a regiospecific manner to afford the corresponding 3,5-disubstituted diastereomeric isoxazolidines in good yields. The stereoselectivity was dependent on the steric hindrance of the nitrone. The major products were found to have the C-3/C-4’ erythro and C-3/C-5 cis relative configuration. Its formation can be rationalized by less hindered attack of the Z-nitrone in an antiperiplanar manner with respect to the largest group of the cyclic acetal.

cycloadditions - nitrones - isoxazolidines - stereoselectivity - heterocycles

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