Stereoselective synthesis of constrained norbornane-derived spiro-beta-lactams (Articolo in rivista)

Type
Label
  • Stereoselective synthesis of constrained norbornane-derived spiro-beta-lactams (Articolo in rivista) (literal)
Anno
  • 2013-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.tet.2012.11.048 (literal)
Alternative label
  • Giuseppe Cremonesi, Piero Dalla Croce, Alessandra Forni, Concetta La Rosa (2013)
    Stereoselective synthesis of constrained norbornane-derived spiro-beta-lactams
    in Tetrahedron (Oxf., Print); Elsevier Ltd, Oxford (Regno Unito)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Giuseppe Cremonesi, Piero Dalla Croce, Alessandra Forni, Concetta La Rosa (literal)
Pagina inizio
  • 1175 (literal)
Pagina fine
  • 1182 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url
  • http://www.elsevier.com/locate/tet (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 69 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 8 (literal)
Note
  • Scopus (literal)
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Universita' degli Studi di Milano e DISFARM e Sezione di Chimica Generale e Organica 'A. Marchesini', V. Venezian 21, I-20133 Milano, Italy CNR-ISTM, V. Golgi 19, I-20133 Milano, Italy (literal)
Titolo
  • Stereoselective synthesis of constrained norbornane-derived spiro-beta-lactams (literal)
Abstract
  • New enantiopure polycyclic norbornane-derived spiro-b-lactams were synthesized by means of a Staudinger ketene-imine reaction between unsymmetrical bicyclic chiral ketenes, generated from differently substituted norbornane carboxylic acids, and (E)-N-benzyl-N-(phenylmethylene)amine, with high yields and moderate to good stereoselectivities. The diastereoisomeric results were rationalized taking into account the increasing steric encumbrance present on the norbornane skeleton and the stability of the products. The configurations of the newly formed stereocenters of spiro-b-lactams were assigned on the basis of 2D NMR experiments and X-ray analysis. Spiro-b-lactams were subjected to acid hydrolysis obtaining the corresponding norbornane-derived b-amino acids. (literal)
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