Ethynylglycine Synthon from Garner's aldehyde: a Useful Precursor for the Synthesis of Non-natural Amino Acids (Articolo in rivista)

Type
Label
  • Ethynylglycine Synthon from Garner's aldehyde: a Useful Precursor for the Synthesis of Non-natural Amino Acids (Articolo in rivista) (literal)
Anno
  • 2005-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1007/s00726-005-0184-y (literal)
Alternative label
  • Reginato, Gianna; Meffre, Patrick; Gaggini, Francesca (2005)
    Ethynylglycine Synthon from Garner's aldehyde: a Useful Precursor for the Synthesis of Non-natural Amino Acids
    in Amino acids (Wien, Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Reginato, Gianna; Meffre, Patrick; Gaggini, Francesca (literal)
Pagina inizio
  • 81 (literal)
Pagina fine
  • 87 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 29 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 6 (literal)
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Meffre P. Centre Universitaire de Formation et de Recherche de N?mes, Site des Carmes, N?mes, France Gaggini F. Dipartimento di Chimica Organica ''U. Schiff'' Università di Firenze, Sesto Fiorentino, Italy (literal)
Titolo
  • Ethynylglycine Synthon from Garner's aldehyde: a Useful Precursor for the Synthesis of Non-natural Amino Acids (literal)
Abstract
  • The ethynylglycine synthon, namely (R)-2,2-dimethyl-3-(tertbutoxycarbonyl)- 4-ethynyl-oxazolidine, can be obtained through the synthetic elaboration of naturally occurring serine. This compound has been exploited as a helpful and versatile non-racemic building block to be used for the design and synthesis of biologically important compounds, mainly non-natural ?-amino acids. Taking advantage of the terminal acetylene moiety several synthetic applications can be designed. Metalation followed by trapping with electrophiles or Cu=Pd catalysed coupling with aromatic halogenides are shown to deliver useful precursors of ethynylglycine derivatives. Additions of bimetallic reagents like stannyl- or silylcuprates are useful entries for the regio- and stereoselective functionalization of the lateral chain, aimed at the synthesis of modified vinylglycine precursors. An overview of our recent work in the field will be given, and the use of ethynylglycine synthon in the synthesis of non-racemic saturated and unsaturated non-natural amino acids will be briefly reviewed. (literal)
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