Stereoselective synthesis of beta-substituted-L-threonines from enantiopure 5-acetyl-2-isoxazolines (Articolo in rivista)

Type
Label
  • Stereoselective synthesis of beta-substituted-L-threonines from enantiopure 5-acetyl-2-isoxazolines (Articolo in rivista) (literal)
Anno
  • 2011-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.tet.2011.02.055 (literal)
Alternative label
  • Cremonesi, Giuseppe; Dalla Croce, Piero; Forni, Alessandra; Gallanti, Maddalena; La Rosa, Concetta (2011)
    Stereoselective synthesis of beta-substituted-L-threonines from enantiopure 5-acetyl-2-isoxazolines
    in Tetrahedron (Oxf., Print); pergamon press, new york (Stati Uniti d'America)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Cremonesi, Giuseppe; Dalla Croce, Piero; Forni, Alessandra; Gallanti, Maddalena; La Rosa, Concetta (literal)
Pagina inizio
  • 2925 (literal)
Pagina fine
  • 2933 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://www.journals.elsevier.com/tetrahedron/ (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 67 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 9 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 16 (literal)
Note
  • ISI Web of Science (WoS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • University of Milan; University of Milan; Consiglio Nazionale delle Ricerche (CNR) (literal)
Titolo
  • Stereoselective synthesis of beta-substituted-L-threonines from enantiopure 5-acetyl-2-isoxazolines (literal)
Abstract
  • Enantiomerically pure, 3-methyl- or 3-ethoxycarbonyl-substituted (5S)- and (5R)-5-acetyl-2-isoxazolines were obtained from the corresponding racemic mixtures by means of an enzymatic reduction with baker's yeast, followed by the separation of the enantiopure syn- and anti-alcohols and oxidation of the alcohol group. The reaction between these ketones and (2R)-Schollkopf's bislactim ether azaenolate was studied: using (55)- and (5R)-3-methyl derivatives, two diastereoisomeric adducts were obtained in good yield and stereoselectivity, whereas reaction with the (55)- and (5R)-3-ethoxycarbonyl derivatives led to a complex mixture of products. Subsequent controlled hydrolysis of the pyrazine ring led to beta-(3-methyl-4,5-dihydro-isoxazol-5-yl)-L-threonines methyl ester together with the corresponding (R)-valine dipeptides. (C) 2011 Elsevier Ltd. All rights reserved. (literal)
Editore
Prodotto di
Autore CNR
Insieme di parole chiave

Incoming links:


Prodotto
Autore CNR di
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi
Editore di
Insieme di parole chiave di
data.CNR.it