Bifunctional Copper Catalysts. A one step synthesis of Bicyclic Ethers Starting from alfa, beta -Unsaturated Ketones (Articolo in rivista)

Type
Label
  • Bifunctional Copper Catalysts. A one step synthesis of Bicyclic Ethers Starting from alfa, beta -Unsaturated Ketones (Articolo in rivista) (literal)
Anno
  • 1997-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/S0040-4039(97)01631-6 (literal)
Alternative label
  • N.Ravasio, V.Leo, F.Babudri, M.Gargano (1997)
    Bifunctional Copper Catalysts. A one step synthesis of Bicyclic Ethers Starting from alfa, beta -Unsaturated Ketones
    in Tetrahedron letters; Pergamon Press, Frankfurt (Regno Unito)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • N.Ravasio, V.Leo, F.Babudri, M.Gargano (literal)
Pagina inizio
  • 7103 (literal)
Pagina fine
  • 7106 (literal)
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  • recensito su ChemInform DOI: 10.1002/chin.199802128 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 38 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 4 (literal)
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  • 40 (literal)
Note
  • ISI Web of Science (WOS) (literal)
  • Scopu (literal)
  • SCImago (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • CNR centro MISO e Dipartimento di Chimica dell'Università, via Amendola 173, 70126 Bari (literal)
Titolo
  • Bifunctional Copper Catalysts. A one step synthesis of Bicyclic Ethers Starting from alfa, beta -Unsaturated Ketones (literal)
Abstract
  • A new, one pot synthesis of bicyclic ethers starting from ?,?-unsaturated ketones containing an additional isolated olefinic bond is proposed. It relies on highly chemoselective hydrogenation of the enone group to the corresponding alcohol in the presence of supported copper catalysts, and on the presence of acidic sites on the catalyst support activating the double bond as a carbocation. (literal)
  • A one pot synthesis of bicyclic ethers starting from 4,-unsatd. ketones contg. an addnl. isolated olefinic bond was described. The synthesis relied on highly chemoselective hydrogenation of the enone group to the corresponding alc. in the presence of silica-titania or silica-zirconia supported copper catalysts, and on the presence of acidic sites on the catalyst support activating the double bond as a carbocation. E.g., carvone was cyclized in the presence of SiO2-TiO2 supported Cu in a H2 atm. at 90° to form bicyclic ether I with 61% yield and 84:16 ratio of exo:endo isomers. ?-Ionone was similarly cyclized using SiO2-ZrO2 supported Cu to form bicyclic ether II as the major diastereoisomer with 61% overall yield. (literal)
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