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- Saegusa–Ito_oxidation abstract "The Saegusa–Ito oxidation is a chemical reaction used in organic chemistry. It was discovered in 1978 by Takeo Saegusa and Yoshihiko Ito as a method to introduce α-β unsaturation in carbonyl compounds. The reaction as originally reported involved formation of a silyl enol ether followed by treatment with palladium(II) acetate and benzoquinone to yield the corresponding enone. The original publication noted its utility for regeneration of unsaturation following 1,4-addition with nucleophiles such as organocuprates.For acyclic substrates the reaction yields the thermodynamic E-olefin product exclusively.This discovery was preceded nearly eight years earlier by a report that treatment of unactivated ketones with palladium acetate yielded the same products in low yields. The major improvement provided by Saegusa and Ito was the recognition that the enol form was the reactive species, developing a method based on silyl enol ethers.Benzoquinone is actually not a necessary component for this reaction; its role is to regenerate palladium(II) from its reduced form palladium(0), so that a smaller amount of expensive palladium(II) acetate is required at the beginning. The reaction conditions and purifications could be easily simplified by just using excess of palladium(II) acetate without benzoquinone, while at a much higher cost. Since the reaction typically employs near-stoichiometric amounts of palladium and is therefore often considered too expensive for industrial usage, some progress has been made in the development of catalytic variants. Despite this shortcoming, the Saegusa oxidation has been used in a number of syntheses as a mild, late-stage method for introduction of functionality in complex molecules.".
- Saegusa–Ito_oxidation thumbnail SaegusaOxidationIntro.png?width=300.
- Saegusa–Ito_oxidation wikiPageID "30159037".
- Saegusa–Ito_oxidation wikiPageLength "10470".
- Saegusa–Ito_oxidation wikiPageOutDegree "63".
- Saegusa–Ito_oxidation wikiPageRevisionID "632391126".
- Saegusa–Ito_oxidation wikiPageWikiLink 1,4-Benzoquinone.
- Saegusa–Ito_oxidation wikiPageWikiLink Acetal.
- Saegusa–Ito_oxidation wikiPageWikiLink Acetic_acid.
- Saegusa–Ito_oxidation wikiPageWikiLink Alkene.
- Saegusa–Ito_oxidation wikiPageWikiLink Alzheimers_disease.
- Saegusa–Ito_oxidation wikiPageWikiLink Beta-Hydride_elimination.
- Saegusa–Ito_oxidation wikiPageWikiLink Carbamate.
- Saegusa–Ito_oxidation wikiPageWikiLink Carbonyl.
- Saegusa–Ito_oxidation wikiPageWikiLink Carbonyl_compound.
- Saegusa–Ito_oxidation wikiPageWikiLink Carvone.
- Saegusa–Ito_oxidation wikiPageWikiLink Catalysis.
- Saegusa–Ito_oxidation wikiPageWikiLink Catalytic.
- Saegusa–Ito_oxidation wikiPageWikiLink Category:Name_reactions.
- Saegusa–Ito_oxidation wikiPageWikiLink Chemical_equilibrium.
- Saegusa–Ito_oxidation wikiPageWikiLink Chemical_reaction.
- Saegusa–Ito_oxidation wikiPageWikiLink Cis–trans_isomerism.
- Saegusa–Ito_oxidation wikiPageWikiLink Deprotection.
- Saegusa–Ito_oxidation wikiPageWikiLink Diels-Alder.
- Saegusa–Ito_oxidation wikiPageWikiLink Diels–Alder_reaction.
- Saegusa–Ito_oxidation wikiPageWikiLink E-selectivity.
- Saegusa–Ito_oxidation wikiPageWikiLink Enol.
- Saegusa–Ito_oxidation wikiPageWikiLink Enone.
- Saegusa–Ito_oxidation wikiPageWikiLink Ether.
- Saegusa–Ito_oxidation wikiPageWikiLink Galantamine.
- Saegusa–Ito_oxidation wikiPageWikiLink Galantamine_total_synthesis.
- Saegusa–Ito_oxidation wikiPageWikiLink Galanthamine.
- Saegusa–Ito_oxidation wikiPageWikiLink Galanthamine_total_synthesis.
- Saegusa–Ito_oxidation wikiPageWikiLink Halogen.
- Saegusa–Ito_oxidation wikiPageWikiLink Jiro_Tsuji.
- Saegusa–Ito_oxidation wikiPageWikiLink Ketone.
- Saegusa–Ito_oxidation wikiPageWikiLink Larry_E._Overman.
- Saegusa–Ito_oxidation wikiPageWikiLink Morphine.
- Saegusa–Ito_oxidation wikiPageWikiLink Natural_product.
- Saegusa–Ito_oxidation wikiPageWikiLink Nucleophile.
- Saegusa–Ito_oxidation wikiPageWikiLink Organic_chemistry.
- Saegusa–Ito_oxidation wikiPageWikiLink Organocopper_compound.
- Saegusa–Ito_oxidation wikiPageWikiLink Palladium(II)_acetate.
- Saegusa–Ito_oxidation wikiPageWikiLink Protecting_group.
- Saegusa–Ito_oxidation wikiPageWikiLink Pyridinium_chlorochromate.
- Saegusa–Ito_oxidation wikiPageWikiLink Reaction_mechanism.
- Saegusa–Ito_oxidation wikiPageWikiLink Reductive_elimination.
- Saegusa–Ito_oxidation wikiPageWikiLink Samuel_J._Danishefsky.
- Saegusa–Ito_oxidation wikiPageWikiLink Selenoxide_elimination.
- Saegusa–Ito_oxidation wikiPageWikiLink Silyl_enol_ether.
- Saegusa–Ito_oxidation wikiPageWikiLink Stoichiometry.
- Saegusa–Ito_oxidation wikiPageWikiLink Strychnine.
- Saegusa–Ito_oxidation wikiPageWikiLink Strychnine_total_synthesis.
- Saegusa–Ito_oxidation wikiPageWikiLink Sulfonate.
- Saegusa–Ito_oxidation wikiPageWikiLink Takeo_Saegusa.
- Saegusa–Ito_oxidation wikiPageWikiLink Tetrahydropyran.
- Saegusa–Ito_oxidation wikiPageWikiLink Thermodynamic_versus_kinetic_reaction_control.
- Saegusa–Ito_oxidation wikiPageWikiLink Tohru_Fukuyama.
- Saegusa–Ito_oxidation wikiPageWikiLink Yoshihiko_Ito_(chemist).
- Saegusa–Ito_oxidation wikiPageWikiLink Β-hydride_elimination.
- Saegusa–Ito_oxidation wikiPageWikiLink File:Acyclic.png.
- Saegusa–Ito_oxidation wikiPageWikiLink File:DanishefskyPeribysinSaegusa.png.
- Saegusa–Ito_oxidation wikiPageWikiLink File:FukuyamaMorphineSaegusa.png.
- Saegusa–Ito_oxidation wikiPageWikiLink File:Larockcatalyticsaegusa.png.
- Saegusa–Ito_oxidation wikiPageWikiLink File:NishidaPlatyphilideSaegusa.png.
- Saegusa–Ito_oxidation wikiPageWikiLink File:OvermanLaurenyneSaegusa.png.
- Saegusa–Ito_oxidation wikiPageWikiLink File:SaegusaMechanism.png.
- Saegusa–Ito_oxidation wikiPageWikiLink File:SaegusaOxidationIntro.png.
- Saegusa–Ito_oxidation wikiPageWikiLink File:ShibasakiStrychnineSaegusa.png.
- Saegusa–Ito_oxidation wikiPageWikiLink File:TsujiAllylcarbonateSaegusa.png.
- Saegusa–Ito_oxidation wikiPageWikiLink File:WangGalanthamineSaegusa.png.
- Saegusa–Ito_oxidation wikiPageWikiLink File:WilliamsSambutoxinSaegusa.png.
- Saegusa–Ito_oxidation wikiPageWikiLinkText "Saegusa–Ito oxidation".
- Saegusa–Ito_oxidation hasPhotoCollection Saegusa–Ito_oxidation.
- Saegusa–Ito_oxidation wikiPageUsesTemplate Template:Colbegin.
- Saegusa–Ito_oxidation wikiPageUsesTemplate Template:Colend.
- Saegusa–Ito_oxidation wikiPageUsesTemplate Template:Good_article.
- Saegusa–Ito_oxidation wikiPageUsesTemplate Template:Reflist.
- Saegusa–Ito_oxidation subject Category:Name_reactions.
- Saegusa–Ito_oxidation comment "The Saegusa–Ito oxidation is a chemical reaction used in organic chemistry. It was discovered in 1978 by Takeo Saegusa and Yoshihiko Ito as a method to introduce α-β unsaturation in carbonyl compounds. The reaction as originally reported involved formation of a silyl enol ether followed by treatment with palladium(II) acetate and benzoquinone to yield the corresponding enone.".
- Saegusa–Ito_oxidation label "Saegusa–Ito oxidation".
- Saegusa–Ito_oxidation sameAs 三枝・伊藤酸化.
- Saegusa–Ito_oxidation sameAs m.0g5955f.
- Saegusa–Ito_oxidation sameAs Q4385739.
- Saegusa–Ito_oxidation sameAs Q4385739.
- Saegusa–Ito_oxidation sameAs Saegusa-Ito氧化反应.
- Saegusa–Ito_oxidation wasDerivedFrom Saegusa–Ito_oxidation?oldid=632391126.
- Saegusa–Ito_oxidation depiction SaegusaOxidationIntro.png.
- Saegusa–Ito_oxidation isPrimaryTopicOf Saegusa–Ito_oxidation.