Asymmetric synthesis of 1,3-thiazolidine-derived spiro-beta-lactams via a Staudinger reaction between chiral ketenes and imines (Articolo in rivista)

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  • Asymmetric synthesis of 1,3-thiazolidine-derived spiro-beta-lactams via a Staudinger reaction between chiral ketenes and imines (Articolo in rivista) (literal)
Anno
  • 2005-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.tetasy.2005.08.054 (literal)
Alternative label
  • Cremonesi G., Dalla Croce P., Fontana F., Forni A., La Rosa C. (2005)
    Asymmetric synthesis of 1,3-thiazolidine-derived spiro-beta-lactams via a Staudinger reaction between chiral ketenes and imines
    in Tetrahedron: asymmetry (Print); PERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD (Regno Unito)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Cremonesi G., Dalla Croce P., Fontana F., Forni A., La Rosa C. (literal)
Pagina inizio
  • 3371 (literal)
Pagina fine
  • 3379 (literal)
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  • IF 2005: 2.429; SJR 2005: Inorganic Chemistry, Q1 (literal)
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  • http://www.sciencedirect.com.pros.lib.unimi.it/science/article/pii/S0957416605007482 (literal)
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  • 16 (literal)
Rivista
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  • 9 (literal)
Note
  • Scopu (literal)
  • ISI Web of Science (WOS) (literal)
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  • Istituto di Chimica Organica 'A. Marchesini', Facolta' di Farmacia, V. Venezian 21, I-20133 Milano, Italy; Dipartimento di Chimica Organica e Industriale and C.N.R.-I.S.T.M., V. Venezian 21, I-20133 Milano, Italy; C.N.R.-I.S.T.M., V. Golgi, 19, I-20133 Milano, Italy (literal)
Titolo
  • Asymmetric synthesis of 1,3-thiazolidine-derived spiro-beta-lactams via a Staudinger reaction between chiral ketenes and imines (literal)
Abstract
  • Enantiomerically pure 1,3-thiazolidine-derived spiro-beta-lactams were stereoselectively synthesised by means of a Staudinger ketene-imine reaction starting from optically active N-Boc-1,3-thiazolidine-2-carboxylic acid derivatives and imines. The reactions were stereoselective and afforded spiro-beta-lactams with a relative trans-configuration. The absolute configuration of the new stereocentres was assigned on the basis of the well-accepted mechanism and confirmed by means of the X-ray crystal structure analysis. The spiro-beta-lactams were transformed into enantiomerically pure chiral monocyclic beta-lactams by opening the thiazolidine ring and recovering the chiral auxiliary. (literal)
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