Diastereofacial selectivity in the reaction of chiral N-trimethylsilyl imines with ester enolates: Preparation of trans -azetidin-2-ones in high stereocontrolled fashion (Articolo in rivista)

Type
Label
  • Diastereofacial selectivity in the reaction of chiral N-trimethylsilyl imines with ester enolates: Preparation of trans -azetidin-2-ones in high stereocontrolled fashion (Articolo in rivista) (literal)
Anno
  • 1996-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/0040-4020(95)00997-3 (literal)
Alternative label
  • Cainelli G.; Panunzio M.; Bandini E.; Martelli G.; Spunta G. (1996)
    Diastereofacial selectivity in the reaction of chiral N-trimethylsilyl imines with ester enolates: Preparation of trans -azetidin-2-ones in high stereocontrolled fashion
    in Tetrahedron (Oxf., Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Cainelli G.; Panunzio M.; Bandini E.; Martelli G.; Spunta G. (literal)
Pagina inizio
  • 1685 (literal)
Pagina fine
  • 1698 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://www.sciencedirect.com/science/article/pii/0040402095009973 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 52 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 5 (literal)
Note
  • Scopu (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipto. Chim. G. Ciamician Univ., C.S.F.M.-C.N.R., Via Selmi 2, 40126 Bologna, Italy; I.Co.C.E.A.-CNR, Via Gobetti, 101 40129 Bologna, Italy (literal)
Titolo
  • Diastereofacial selectivity in the reaction of chiral N-trimethylsilyl imines with ester enolates: Preparation of trans -azetidin-2-ones in high stereocontrolled fashion (literal)
Abstract
  • Highly efficient chiral ester enolate-imine condensation, giving 3,4-disubstituted ?-lactams with excellent trans-syn or trans-anti diastereoselectivity, is reported. The chiral information is included in the electrophilic partner of the condensation, nominally chiral ?-, ?-silyloxy- or alkoxy-N-trimethylsilyl-imines. The high diastereofacial selectivity is determined by the correct choice of the metal cations present in the reaction medium and the very nature of the hydroxy protecting group. By this procedure a number of azetidinones, intermediates in the synthesis of commercially interesting ?-lactam antibiotics have been obtained. Fully assigned 1H and 13C NMR spectra of the so obtained azetidinones are reported. (literal)
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