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Synthesis and Stereochemistry of (1S,3S,4S,7R11R)-3-(4-Nitrophenyl)-11-aza-2,6-dioxatricyclo[5,3,1,04,11]undecane

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Abstract

The reaction of (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediol with glutaraldehyde has been studied. It has been established on the basis of AM1 and PM3 calculations and 1H NMR spectra recorded in the presence of the shift reagent Eu(fod)3 that (1S,3S,4S,7R,11R)-3-(4-nitrophenyl)-11-aza-2,6-dioxatricyclo[5,3,1,04,11]undecane is formed as the result of the reaction.

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Authors and Affiliations

  1. Faculté de Farmacie, Université d'Auvergne, 28, Place Henri Dunant, Clermont-Ferrand, France

    J. Couquelet, M. Madesclaire & F. Leal

  2. Samara State University, Samara, 443011, Russia

    V. P. Zaitsev & S. Kh. Sharipova

Authors
  1. J. Couquelet
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  2. M. Madesclaire
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  3. F. Leal
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  4. V. P. Zaitsev
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  5. S. Kh. Sharipova
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Couquelet, J., Madesclaire, M., Leal, F. et al. Synthesis and Stereochemistry of (1S,3S,4S,7R11R)-3-(4-Nitrophenyl)-11-aza-2,6-dioxatricyclo[5,3,1,04,11]undecane. Chemistry of Heterocyclic Compounds 37, 898–902 (2001). https://doi.org/10.1023/A:1012463911175

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  • DOI: https://doi.org/10.1023/A:1012463911175

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