Diastereoselective Preparation of Silylated Pyrrolidones via Palladium-Catalysed Cyclizations (Articolo in rivista)

Type
Label
  • Diastereoselective Preparation of Silylated Pyrrolidones via Palladium-Catalysed Cyclizations (Articolo in rivista) (literal)
Anno
  • 2003-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/ejoc.200300086 (literal)
Alternative label
  • Serge, Thorimbert; Giuliano, Giambastiani; Claude, Commandeur; Maxime, Vitale; Giovanni, Poli; Max, Malacria (2003)
    Diastereoselective Preparation of Silylated Pyrrolidones via Palladium-Catalysed Cyclizations
    in European journal of organic chemistry (Print); Wiley-VCH Verlag, GmbH, Weinheim (Germania)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Serge, Thorimbert; Giuliano, Giambastiani; Claude, Commandeur; Maxime, Vitale; Giovanni, Poli; Max, Malacria (literal)
Pagina inizio
  • 2702 (literal)
Pagina fine
  • 2708 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 7 (literal)
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Laboratoire de Chimie Organique, UMR 7611, Universite P. et M. Curie, 4, Place Jussieu BP 229, 75252 Paris Cedex 05, France; Institute of Chemistry of OrganoMetallic Compounds, ICCOM-CNR, Florence research area, Via Madonna del Piano 10 - 50019 - Sesto Fiorentino - Florence - Italy (literal)
Titolo
  • Diastereoselective Preparation of Silylated Pyrrolidones via Palladium-Catalysed Cyclizations (literal)
Abstract
  • A new palladium-catalysed allylic alkylation affording silylated 3-vinylpyrrolidones has been developed. The method relies upon the interaction between a stabilized acetamide enolate anion and a silicon-containing, nitrogen-tethered ç3-allylpalladium moiety. Two variants have been studied, involving the location of the silicon atom on either olefinic carbon atom of the cyclisation precursor. In both cases 5-exo ring closure was the only cyclisation process observed. The stereoselectivity of these processes is discussed. These results contrast with related â-oxo ester cyclisations, in which competitive 7-endo mode is observed. (literal)
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