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

Type

• Articolo in rivista (Classe)
• Prodotto della ricerca (Classe)

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

• Tetrahedron (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

• pergamon press (Editore)

Prodotto di

• Istituto di scienze e tecnologie molecolari (ISTM) (Istituto)
• Nanoingegneria chimica di sistemi assemblati mediante interazioni intermolecolari specifiche (PM.P07.002.002) (Modulo)

Autore CNR

• ALESSANDRA FORNI (Unità di personale interno)

Insieme di parole chiave

• Keywords of "Stereoselective synthesis of beta-substituted-L-threonines from enantiopure 5-acetyl-2-isoxazolines" (Insieme di parole chiave)

Incoming links:

Prodotto

• Istituto di scienze e tecnologie molecolari (ISTM) (Istituto)
• Nanoingegneria chimica di sistemi assemblati mediante interazioni intermolecolari specifiche (PM.P07.002.002) (Modulo)

Autore CNR di

• ALESSANDRA FORNI (Unità di personale interno)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#rivistaDi

• Tetrahedron (Rivista)

Editore di

• pergamon press (Editore)

Insieme di parole chiave di

• Keywords of "Stereoselective synthesis of beta-substituted-L-threonines from enantiopure 5-acetyl-2-isoxazolines" (Insieme di parole chiave)