http://www.cnr.it/ontology/cnr/individuo/prodotto/ID16627
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
- Pagina fine
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
- Rivista
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
- 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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