title: [2,3]-Sigmatropic rearrangement of allylic selenimides: strategy for the synthesis of peptides, peptidomimetics, and N-aryl vinyl glycines.
abstract: 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.
authors.affiliation: Department of Chemistry, Imperial College London , South Kensington, London SW7 2AZ, U.K.
authors.forename: Alan
authors.initials: A
authors.lastname: Armstrong
authors.forename: Daniel P G
authors.initials: DP
authors.lastname: Emmerson
authors.forename: Harry J
authors.initials: HJ
authors.lastname: Milner
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Sheppard
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D057786:Peptidomimetics / Q000138:chemical synthesis* / Q000737:chemistry; D018036:Selenium Compounds / Q000737:chemistry*
chemical_list: D000498:Allyl Compounds; D010455:Peptides; D057786:Peptidomimetics; D018036:Selenium Compounds; D005998:Glycine