1596354-40-3Relevant articles and documents
[2,3]-sigmatropic rearrangement of allylic selenimides: Strategy for the synthesis of peptides, peptidomimetics, and N-aryl vinyl glycines
Armstrong, Alan,Emmerson, Daniel P. G.,Milner, Harry J.,Sheppard, Robert J.
, p. 3895 - 3907 (2014/05/20)
The scope of the NCS-mediated amination/[2,3]-sigmatropic rearrangement of enantioenriched allylic selenides has been expanded to provide access to three new product classes. The use of N-protected amino acid amides provides a novel strategy for accessing peptide chains containing unnatural vinyl glycine amino acid residues. Also reported is the use of amino acid esters, allowing the diastereoselective synthesis of N,N-dicarboxymethylamines, a motif found in a number of pharmaceuticals. Furthermore, use of a range of N-aromatic and N-heteroaromatic amines allows the formation of enantioenriched N-arylamino acids, a motif found in a number of synthetically and biologically interesting compounds.
