title: Enantioselective synthesis of α-alkyl,α-vinyl amino acids via [2,3]-sigmatropic rearrangement of selenimides.
abstract: Chiral α-alkyl,α-vinyl amino acids (quaternary vinyl glycine derivatives) are prepared with high levels of enantiomeric purity by [2,3]-sigmatropic rearrangement of allylic selenimides. The required trisubstituted allylic selenides are prepared by an organocatalytic α-selenenylation of aldehydes followed by Horner-Wadsworth-Emmons (HWE) olefination. Both (E)-and (Z)-geometrical isomers are available giving access to both enantiomers of the desired products.
authors.affiliation: Department of Chemistry, Imperial College London, London, UK. A.Armstrong@imperial.ac.uk
authors.forename: Alan
authors.initials: A
authors.lastname: Armstrong
authors.forename: Daniel P G
authors.initials: DP
authors.lastname: Emmerson
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005998:Glycine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000475:Alkenes; D000596:Amino Acids; D016566:Organoselenium Compounds; D005998:Glycine