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Issue 11, 1996
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Kinetic and thermodynamic azides from α-triflates of γ-lactones: intermediates for the incorporation of polyhydroxylated D- and L-α-aminoacids into combinatorial libraries

Abstract

Displacement of α-triflates of 2,3,4-all cis-substituted γ-lactones by sodium azide in DMF gives kinetically an azide with inversion of configuration at the C-2 of the lactone; under the reaction conditions, the initially formed azide epimerises to the apparently more crowded and thermodynamically stable all cis-azide, giving intermediates which should readily allow the incorporation of polyhydroxylated amino acids into combinatorial libraries.

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Article type: Paper
DOI: 10.1039/CC9960001271
Citation: Chem. Commun., 1996,0, 1271-1272
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    Kinetic and thermodynamic azides from α-triflates of γ-lactones: intermediates for the incorporation of polyhydroxylated D- and L-α-aminoacids into combinatorial libraries

    T. M. Krülle, B. Davis, H. Ardron, D. D. Long, N. A. Hindle, C. Smith, D. Brown, A. L. Lane, D. J. Watkin, D. G. Marquess and G. W. J. Fleet, Chem. Commun., 1996, 0, 1271
    DOI: 10.1039/CC9960001271

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