[2,3]-Sigmatropic Rearrangement of Allylic Selenimides: Strategy for the Synthesis of Peptides, Peptidomimetics, and N‑Aryl Vinyl Glycines

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 gl...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-05, Vol.79 (9), p.3895-3907
Main Authors: Armstrong, Alan, Emmerson, Daniel P. G, Milner, Harry J, Sheppard, Robert J
Format: Article
Language:English
Subjects:
Allyl Compounds - chemistry
Glycine - analogs & derivatives
Glycine - chemical synthesis
Glycine - chemistry
Molecular Structure
Peptides - chemical synthesis
Peptides - chemistry
Peptidomimetics - chemical synthesis
Peptidomimetics - chemistry
Selenium Compounds - chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo500341e