Synthesis of Alkyl-Substituted Six-Membered Lactones Through Ring-Closing Metathesis of Homoallyl Acrylates. An Easy Route to Pyrans-2-ones, Constituents of Tobacco Flavor (Articolo in rivista)

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  • Synthesis of Alkyl-Substituted Six-Membered Lactones Through Ring-Closing Metathesis of Homoallyl Acrylates. An Easy Route to Pyrans-2-ones, Constituents of Tobacco Flavor (Articolo in rivista) (literal)
Anno
  • 2007-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1021/jo070600h (literal)
Alternative label
  • D'Annibale Andrea; Ciaralli Laura; Bassetti Mauro; Pasquini Chiara (2007)
    Synthesis of Alkyl-Substituted Six-Membered Lactones Through Ring-Closing Metathesis of Homoallyl Acrylates. An Easy Route to Pyrans-2-ones, Constituents of Tobacco Flavor
    in Journal of organic chemistry; ACS, American chemical society, Washington, DC (Stati Uniti d'America)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • D'Annibale Andrea; Ciaralli Laura; Bassetti Mauro; Pasquini Chiara (literal)
Pagina inizio
  • 6067 (literal)
Pagina fine
  • 6074 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 72 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 8 (literal)
Note
  • SciFinder (literal)
  • Scopus (literal)
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Istituto di Metodologie Chimiche, CNR, Roma; Dipartimento di Chimica, Universit√† La Sapienza, Roma (literal)
Titolo
  • Synthesis of Alkyl-Substituted Six-Membered Lactones Through Ring-Closing Metathesis of Homoallyl Acrylates. An Easy Route to Pyrans-2-ones, Constituents of Tobacco Flavor (literal)
Abstract
  • The ring-closing metathesis (RCM) reactions of homoallylic acrylates bearing alkyl substituents on various positions of their skeleton afford the corresponding pentenolides in the presence of carbene ruthenium catalysts. For R-3 = R-4 = H, or R-3 = Me, R-4 = H, the reactions are catalyzed by complex [RuCl2(PCy3)(2)(CHPh)], while a second-generation Grubbs catalyst is required when R-3 = H and R-4 = Me, R-3 = R-4 = Me, or R-3 = i-Pr and R-4 = H. Alkyl substitution at the homoallylic carbon (R-1, R-2) increases the yield of the reaction when both the acrylic and/or homoallylic double bonds are methyl-substituted. The interaction of the catalyst with the substrate in the initiation stage involves the homoallylic double bond rather than the acrylic moiety, and the resulting alkylidene species from the first-generation Grubbs catalyst can be observed by H-1 and P-31 NMR. The racemic tobacco constituents 4-isopropyl-5,6-dihydropyran-2-one and 4-isopropyltetrahydropyran-2-one are prepared via a short reaction sequence, involving the RCM reaction as the key transformation. (literal)
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