Chiral N-hydroxybenzamides as potential catalysts for aerobic asymmetric oxidations (Articolo in rivista)

Type
Label
  • Chiral N-hydroxybenzamides as potential catalysts for aerobic asymmetric oxidations (Articolo in rivista) (literal)
Anno
  • 2014-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1021/jo500844c (literal)
Alternative label
  • M.G. Capraro, P. Franchi, O. Lanzalunga, A. Lapi, M. Lucarini (2014)
    Chiral N-hydroxybenzamides as potential catalysts for aerobic asymmetric oxidations
    in Journal of organic chemistry
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • M.G. Capraro, P. Franchi, O. Lanzalunga, A. Lapi, M. Lucarini (literal)
Pagina inizio
  • 6435 (literal)
Pagina fine
  • 6443 (literal)
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  • http://www.scopus.com/inward/record.url?eid=2-s2.0-84904570532&partnerID=q2rCbXpz (literal)
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  • 79 (literal)
Rivista
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  • 9 (literal)
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  • 14 (literal)
Note
  • ISI Web of Science (WOS) (literal)
  • Scopu (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipartimento di Chimica, Istituto CNR di Metodologie Chimiche (IMC-CNR), Università di Roma la Sapienza, P.le A. Moro, 5, I-00185 Rome, Italy; Dipartimento di Chimica G. Ciamician, Università di Bologna, Via San Giacomo 11, I-40126 Bologna, Italy (literal)
Titolo
  • Chiral N-hydroxybenzamides as potential catalysts for aerobic asymmetric oxidations (literal)
Abstract
  • Chiral N-hydroxybenzamides (1H-3H) have been synthesized as precursors of chiral short-lived N-oxyl radicals 1o-3o. The latter species have been generated by oxidation of 1H-3H with Pb(OAc)4 or hydrogen abstraction from 1H-3H by the tert-butoxyl radical and characterized by UV-vis spectrophotometry and EPR spectroscopy. Through a kinetic study of the hydrogen atom transfer processes promoted by 1o-3o from three chiral benzylic substrates (1- phenylethylamine, 1-phenylethanol, and ?-vinylbenzyl alcohol), a moderate chiral discrimination has been found, with selectivity factors 0.5 <= kH(S)/kH(R) <= 2. (literal)
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