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  • 1.
    Horváth, Attila
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Jonasson, Catrin
    Bäckvall, Jan-Erling
    Intramolecular Palladium(II)-Catalyzed 1,2-Addition to Allenes2000Inngår i: Journal of the American Chemical Society, ISSN 0002-7863, Vol. 122, nr 40, s. 9600-9609Artikkel i tidsskrift (Fagfellevurdert)
  • 2.
    Jonasson, Catrin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Palladium (II)-catalyzed oxidations of allenes and conjugated dienes2000Doktoravhandling, med artikler (Annet vitenskapelig)
  • 3.
    Lindström, Ulf
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Synthesis and [3,3]-Sigmatropic Rearrangement of Vinylaziridines2000Doktoravhandling, med artikler (Annet vitenskapelig)
    Abstract [sv]

    A general synthetic route from vinylepoxides to vinylaziridines via 1,2-amino alcohols was developed. The 1,2-amino alcohols were obtained from a stereospecific and regioselective aminolysis of vinylepoxides. The synthetic scope of the aminolysis could be expanded by the use of a microwave-assisted protocol. Some of the 1,2-amino alcohols were dehydrated with PPh3/DEAD to afford N-H vinylaziridines. All of the so obtained N-H vinylaziridines were acylated to give the corresponding N-acyl vinylaziridines. When variously substituted N-acyl vinylaziridines were subjected to LiHMDS in THF, the resulting amide enolates underwent a stereoselective aza-[3,3]-Claisen rearrangement to give mono-, di- and trisubstituted seven-membered lactams. The scope and limitations of the rearrangement were investigated. Finally, the aminolysis of vinylepoxides was applied in an asymmetric synthesis of (+)-1-deoxynojirimycin.

  • 4.
    Staaf, Mikael
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Structural and conformational studies of bacterial polysaccharides employing NMR spectroscopy2000Doktoravhandling, monografi (Annet vitenskapelig)
    Abstract [en]

    Methods and approaches for performing structural and conformational analysis of bacterial polysaccharides in solution are described. The structure of one exopolysaccharide from Lactobacillus helveticus and two O-antigens from Escherichia coli have been determined using NMR spectroscopy, chemical degradation and mass spectrometry. This thesis discusses different problems encountered in connection with these structural elucidations, namely, overlap of NMR signals, heterogeneity in the polysaccharide sequence and the configurations of a nonulosonic acid.

    A conformational analysis of the enterobacterial common antigen (ECA) in the form of a cyclic dodecamer is described. Nuclear Overhauser effects (NOEs) and heteronuclear three-bond coupling constants (3JCH) over the glycosidic linkages were determined and used to calculate proton-proton distances and torsion angles. Residual dipolar couplings were measured in a liquid crystalline medium. These couplings provide orientational information distinct from that contained in the local NOE and 3JCH data. The experimental data were compared to the averaged distances, three-bond proton-carbon coupling constants and C-H vector orientations in a model obtained by molecular dynamics simulations. From a fragment that were in agreement with experimental data, a three-dimensional structure was generated for the cyclic ECA in solution

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