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Search: WFRF:(Tuzina Pavel) > (2007)

  • Result 1-2 of 2
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1.
  • Blid, Jan, et al. (author)
  • Lewis acid mediated asymmetric 2,3 -sigmatropic rearrangement of allylic amines. Scope and mechanistic investigation
  • 2007
  • In: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 72:4, s. 1294-1300
  • Journal article (peer-reviewed)abstract
    • [GRAPHIC] The first asymmetric [2,3]-sigmatropic rearrangement of achiral allylic amines has been realized by quaternization of the amines with an enantiomerically pure diazaborolidine and subsequent treatment with Et3N. The resultant homoallylic amines were obtained in good yields and excellent ee's. The observed diastereo- and enantioselectivities were rationalized by invoking a kinetically controlled process, and support for this model was obtained from an NMR spectroscopic investigation of the chiral Lewis acid-substrate complex. The structure of the Lewis acid-product complex was established by X-ray crystallographic analysis and supported the proposed mechanism.
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2.
  • Tuzina, Pavel, et al. (author)
  • Lewis acid mediated 1,2 -rearrangement of ammonium ylides
  • 2007
  • In: Tetrahedron Letters. - : Elsevier BV. - 0040-4039 .- 1359-8562. ; 48:28, s. 4947-4949
  • Journal article (peer-reviewed)abstract
    • The first example of Lewis acid mediated [1,2]-rearrangement of various glycine derivatives has been developed. A brief study of steric and electronic properties of the migrating group is presented. The corresponding amides were obtained in good yields and in the case of substrate 4d, moderate diastereoselectivity was observed.
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  • Result 1-2 of 2
Type of publication
journal article (2)
Type of content
peer-reviewed (2)
Author/Editor
Somfai, Peter (2)
Tuzina, Pavel (2)
Blid, Jan (1)
Panknin, Olaf (1)
University
Royal Institute of Technology (2)
Language
English (2)
Research subject (UKÄ/SCB)
Natural sciences (2)
Year
2007 (2)Undo refine

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