BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - AN ENANTIOSPECIFIC SYNTHESIS OF MONOCYCLIC BETA-LACTAMS (Articolo in rivista)

Type
Label
  • BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - AN ENANTIOSPECIFIC SYNTHESIS OF MONOCYCLIC BETA-LACTAMS (Articolo in rivista) (literal)
Anno
  • 1991-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/S0040-4020(01)86509-1 (literal)
Alternative label
  • ANDREOLI, P; BILLI, L; CAINELLI, G; PANUNZIO, M; BANDINI, E; MARTELLI, G; SPUNTA, G (1991)
    BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - AN ENANTIOSPECIFIC SYNTHESIS OF MONOCYCLIC BETA-LACTAMS
    in Tetrahedron (Oxf., Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • ANDREOLI, P; BILLI, L; CAINELLI, G; PANUNZIO, M; BANDINI, E; MARTELLI, G; SPUNTA, G (literal)
Pagina inizio
  • 9061 (literal)
Pagina fine
  • 9070 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://www.sciencedirect.com/science/article/pii/S0040402001865091 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 47 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 10 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 43 (literal)
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • University of Bologna; Consiglio Nazionale delle Ricerche (CNR); Consiglio Nazionale delle Ricerche (CNR) (literal)
Titolo
  • BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - AN ENANTIOSPECIFIC SYNTHESIS OF MONOCYCLIC BETA-LACTAMS (literal)
Abstract
  • Optically active 3,4-disubstituted azetidin-2-ones have been prepared by annelation of chiral silylimines derived from (S) or (R)-lactaldehyde with the ester enolate of the ethyl 2,2,5,5,-tetramethyl-1,2,5-azadisilolidin-1-acetate (STABASE). Oxidation of the hydroxyethyl side chain on the C-4 position of the beta-lactam ring, followed by Baeyer-Villiger oxidation led to the optically active (3S, 4S) 3-amino-4-acetoxy-beta-lactam. The absolute configuration of this compound was determined by elaboration of this substrate to a key intermediate in the synthesis of the antibiotic ''Aztreonam''. Nucleophilic displacement of the acetoxy group led to optically active 3-amino-4-alkyl (aryl)-azetidin-2-ones. (literal)
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