Cyclohexanones derived from dihydrocarvone as precursor of chiral dioxiranes for epoxidation of olefins (Articolo in rivista)

Type
Label
  • Cyclohexanones derived from dihydrocarvone as precursor of chiral dioxiranes for epoxidation of olefins (Articolo in rivista) (literal)
Anno
  • 2004-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.tet.2004.09.089 (literal)
Alternative label
  • Solladie-Cavallo A.; Jierry L.; Lupattelli P.; Bovicelli P.; Antonioletti R. (2004)
    Cyclohexanones derived from dihydrocarvone as precursor of chiral dioxiranes for epoxidation of olefins
    in Tetrahedron (Oxf., Print)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Solladie-Cavallo A.; Jierry L.; Lupattelli P.; Bovicelli P.; Antonioletti R. (literal)
Pagina inizio
  • 11375 (literal)
Pagina fine
  • 11381 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 60 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 50 (literal)
Note
  • ISI Web of Science (WOS) (literal)
  • Scopu (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Univ Strasbourg 1, CNRS, ECPM, France; Univ Basilicata, Potenza CNR - Istituto di Chimica Biomolecolare, UOS Roma (literal)
Titolo
  • Cyclohexanones derived from dihydrocarvone as precursor of chiral dioxiranes for epoxidation of olefins (literal)
Abstract
  • New ketones having an axial a-fluorine atom and substituents other than fluorine at C8, derived from commercially available (+)-dihydrocarvone, have been prepared and used for epoxidations of trans stilbene, trans methyl p-methoxy cinnamate, trans cinnamyl alcohol and derivatives. It was found that replacement of the H at C8 by a substituent containing an oxygen atom increases the enantioselectivities in all cases. It was also shown that protic substituents (hydroxyl groups) provide a decrease in enantioselectivity in the case of cinnamates probably because of H-bonding dioxirane-substrate. It is noted that the absolute configurations of the various epoxides obtained hold with the usual model involving a spiro-approach on the dioxirane conformation C1 having the a-fluorine axial. Moreover, sub-stoichiometric amounts (0.3 equiv) of ketone can be used in all cases as these ketones do not undergo Baeyer-Villiger oxidation and are recovered. (C) 2004 Elsevier Ltd. All rights reserved. (literal)
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