Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation (Articolo in rivista)

Type
Label
  • Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation (Articolo in rivista) (literal)
Anno
  • 2014-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1002/ejoc.201403180 (literal)
Alternative label
  • Barrulas, Pedro C.; Genoni, Andrea; Benaglia, Maurizio; Burke, Anthony J. (2014)
    Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation
    in European journal of organic chemistry (Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Barrulas, Pedro C.; Genoni, Andrea; Benaglia, Maurizio; Burke, Anthony J. (literal)
Pagina inizio
  • 7339 (literal)
Pagina fine
  • 7342 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 4 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 33 (literal)
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • University of Evora; University of Evora; University of Milan; Consiglio Nazionale delle Ricerche (CNR) (literal)
Titolo
  • Cinchona-Derived Picolinamides: Effective Organocatalysts for Stereoselective Imine Hydrosilylation (literal)
Abstract
  • Picolinamide-cinchona organocatalysts for the successful enantioselective reduction of ketomines were developed. For the first time, a new type of chiral Lewis base, a cationic species, is reported to efficiently organocatalyze the addition of trichlorosilane to imines. Excellent yields with good to high enantioselectivities (up to 91%) were obtained in the reduction of differently substituted substrates. Noteworthy, remarkably high turnover frequencies for the hydrosilylation of imines were observed; the catalyst of choice proved to be active even at a loading of only 1 mol-%. The loading was further reduced to 0.5 mol-%, and for very short reaction times (15 min) very impressive asymmetric catalyst efficiency speed values were reached. (literal)
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