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Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids

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  • James A. Workman
  • Neil P. Garrido
  • Julien Sançon
  • Edward Roberts
  • Hans Peter Wessel
  • J. B. Sweeney
<mark>Journal publication date</mark>2/02/2005
<mark>Journal</mark>Journal of the American Chemical Society
Issue number4
Number of pages2
Pages (from-to)1066-1067
Publication StatusPublished
<mark>Original language</mark>English


The first examples of highly enantioselective [2,3]-sigmatropic rearrangements of acyclic allylic ammonium ylids are reported. Thus, a range of N-{2′-[(N′-allyl-N′,N′-dialkyl)ammonium]}acetyl camphor sultams undergo rearrangement at 0 °C in DME solution with high diastereofacial control (up to 99:1 dr) to give allylglycines in generally high yield. The power of the method has been demonstrated in a rapid and efficient synthesis of (R)-allyl glycine.