Steric and electronic tuning of chiral bis(oxazoline) ligands with 3,3'-bithiophene backbone (Articolo in rivista)

Type
Label
  • Steric and electronic tuning of chiral bis(oxazoline) ligands with 3,3'-bithiophene backbone (Articolo in rivista) (literal)
Anno
  • 2005-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1021/jo050267m (literal)
Alternative label
  • Benaglia, M.; Benincori, T.; Mussini, P.; Pilati, T.; Rizzo, S.; Sannicolò, F. (2005)
    Steric and electronic tuning of chiral bis(oxazoline) ligands with 3,3'-bithiophene backbone
    in Journal of organic chemistry
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Benaglia, M.; Benincori, T.; Mussini, P.; Pilati, T.; Rizzo, S.; Sannicolò, F. (literal)
Pagina inizio
  • 7488 (literal)
Pagina fine
  • 7495 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 70 (literal)
Rivista
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Benaglia, M.: Dipartimento di Chimica Organica e Industriale dell'Università , via Golgi 19-20133 Milano, Italy. Benincori, T.: Dipartimento di Scienze Chimiche ed Ambientali dell'Università dell'Insubria, Via Valleggio, 11-22100 Como, Italy. Mussini, P.: Dipartimento di Chimica Fisica ed Elettrochimica dell'Università, via Golgi, 19-20133 Milano, Italy. Pilati, T.; Rizzo, S.: Istituto CNR Scienze e Tecnologie Molecolari, via C. Golgi, 19-20133 Milan, Italy. Sannicolò, F.: Dipartimento di Chimica Organica e Industriale dell'Università , via Golgi 19-20133 Milano, Italy; Istituto CNR Scienze e Tecnologie Molecolari, via C. Golgi, 19-20133 Milan, Italy; and CIMAINA - Centro Interdisciplinare Materiali e Interfacce Nanostrutturati, Via Celoria, 16-20133 Milano, Italy. (literal)
Titolo
  • Steric and electronic tuning of chiral bis(oxazoline) ligands with 3,3'-bithiophene backbone (literal)
Abstract
  • The role played by the electronic properties and the steric features of bis(oxazoline) ligands in the Cu(I)-catalyzed cyclopropanation of styrene effected with ethyl diazoacetate was investigated. Two pairs of new bis(oxazolines) displaying flexible and atropisomeric 3,3¢-bithiophene backbones were synthesized and structurally and electronically characterized. For the first time, the electrochemical oxidative potential was used as a reliable index of the electronic density on the nitrogen atom of the chelating groups of new and, for comparative purposes, of already known bis(oxazolines). The Cu(I) complexes of the new ligands were prepared, and their enantioselection ability and catalytic efficiency were tested. This investigation suggests that steric factors and catalyst geometrical features are clearly more important than any consideration of the electronic properties of the chiral ligands. (literal)
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