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- Danishefskys_diene abstract "Danishefsky’s diene (Kitahara diene) is an organosilicon compound and a diene with the formal name trans-1-methoxy-3-trimethylsilyloxy-1,3-butadiene named after Samuel J. Danishefsky. Because the diene is very electron-rich it is a very reactive reagent in Diels-Alder reactions. This diene reacts rapidly with electrophilic alkenes, such as maleic anhydride. The methoxy group promotes highly regioselective additions. The diene is known to react with amines, aldehydes, alkenes and alkynes. Reactions with imines and nitro-olefins have been reported.It was first synthesized by the reaction of trimethylsilyl chloride with 4-methoxy-3-buten-2-one and zinc chloride:The diene has two features of interest: the substituents promote regiospecific addition to unsymmetrical dienophiles and the resulting adduct is amenable to further functional group manipulations after the addition reaction. High regioselectivity is obtained with unsymmetrical alkenes with a preference for a 1,2-relation of the ether group with the electron-deficient alkene-carbon. All this is exemplified in this Aza Diels-Alder reaction:In the cycloaddition product, the silyl ether is a synthon for a carbonyl group via the enol. The methoxy group is susceptible to an elimination reaction enabling the formation of a new alkene group.Applications in asymmetric synthesis have been reported. Derivatives have been reported.".
- Danishefskys_diene thumbnail Danishefsky-Diene_Structural_Formulae.png?width=300.
- Danishefskys_diene wikiPageID "7067238".
- Danishefskys_diene wikiPageLength "9310".
- Danishefskys_diene wikiPageOutDegree "29".
- Danishefskys_diene wikiPageRevisionID "668326165".
- Danishefskys_diene wikiPageWikiLink Aldehyde.
- Danishefskys_diene wikiPageWikiLink Alkene.
- Danishefskys_diene wikiPageWikiLink Alkyne.
- Danishefskys_diene wikiPageWikiLink Amine.
- Danishefskys_diene wikiPageWikiLink Aza-Diels–Alder_reaction.
- Danishefskys_diene wikiPageWikiLink Carbonyl.
- Danishefskys_diene wikiPageWikiLink Category:Dienes.
- Danishefskys_diene wikiPageWikiLink Category:Reagents_for_organic_chemistry.
- Danishefskys_diene wikiPageWikiLink Category:Silanes.
- Danishefskys_diene wikiPageWikiLink Diels–Alder_reaction.
- Danishefskys_diene wikiPageWikiLink Diene.
- Danishefskys_diene wikiPageWikiLink Elimination_reaction.
- Danishefskys_diene wikiPageWikiLink Enantioselective_synthesis.
- Danishefskys_diene wikiPageWikiLink Enol.
- Danishefskys_diene wikiPageWikiLink Maleic_anhydride.
- Danishefskys_diene wikiPageWikiLink Methoxy.
- Danishefskys_diene wikiPageWikiLink Organosilicon.
- Danishefskys_diene wikiPageWikiLink Reagent.
- Danishefskys_diene wikiPageWikiLink Regioselectivity.
- Danishefskys_diene wikiPageWikiLink Samuel_J._Danishefsky.
- Danishefskys_diene wikiPageWikiLink Silyl_ether.
- Danishefskys_diene wikiPageWikiLink Synthon.
- Danishefskys_diene wikiPageWikiLink Trimethylsilyl_chloride.
- Danishefskys_diene wikiPageWikiLink Zinc_chloride.
- Danishefskys_diene wikiPageWikiLink File:AzaDA_DanishefskyDiene.png.
- Danishefskys_diene wikiPageWikiLink File:Danishefskys_diene_application2.png.
- Danishefskys_diene wikiPageWikiLinkText "Danishefsky's diene".
- Danishefskys_diene wikiPageWikiLinkText "Danishefsky-type diene".
- Danishefskys_diene imagealt "Ball-and-stick model of Danishefsky's diene".
- Danishefskys_diene imagealt "Structural formula of Danishefsky's diene".
- Danishefskys_diene imagefile "Danishefsky's diene 3D ball.png".
- Danishefskys_diene imagefile "Danishefsky-Diene Structural Formulae.png".
- Danishefskys_diene imagesize "160".
- Danishefskys_diene imagesize "180".
- Danishefskys_diene othernames "-1".
- Danishefskys_diene othernames "Kitahara diene".
- Danishefskys_diene othernames "trans-1-Methoxy-3-trimethylsilyloxy-1,3-butadiene".
- Danishefskys_diene verifiedrevid "401977521".
- Danishefskys_diene watchedfields "changed".
- Danishefskys_diene wikiPageUsesTemplate Template:Chembox.
- Danishefskys_diene wikiPageUsesTemplate Template:Chembox_Hazards.
- Danishefskys_diene wikiPageUsesTemplate Template:Chembox_Identifiers.
- Danishefskys_diene wikiPageUsesTemplate Template:Chembox_Properties.
- Danishefskys_diene wikiPageUsesTemplate Template:Chemspidercite.
- Danishefskys_diene wikiPageUsesTemplate Template:Reflist.
- Danishefskys_diene wikiPageUsesTemplate Template:S23.
- Danishefskys_diene wikiPageUsesTemplate 25.
- Danishefskys_diene wikiPageUsesTemplate Template:Stdinchicite.
- Danishefskys_diene subject Category:Dienes.
- Danishefskys_diene subject Category:Reagents_for_organic_chemistry.
- Danishefskys_diene subject Category:Silanes.
- Danishefskys_diene hypernym Compound.
- Danishefskys_diene type ChemicalCompound.
- Danishefskys_diene type ChemicalSubstance.
- Danishefskys_diene type Alkene.
- Danishefskys_diene type Chemical.
- Danishefskys_diene type Diene.
- Danishefskys_diene type Hydride.
- Danishefskys_diene type Reagent.
- Danishefskys_diene type ChemicalObject.
- Danishefskys_diene type Thing.
- Danishefskys_diene type Q11173.
- Danishefskys_diene comment "Danishefsky’s diene (Kitahara diene) is an organosilicon compound and a diene with the formal name trans-1-methoxy-3-trimethylsilyloxy-1,3-butadiene named after Samuel J. Danishefsky. Because the diene is very electron-rich it is a very reactive reagent in Diels-Alder reactions. This diene reacts rapidly with electrophilic alkenes, such as maleic anhydride. The methoxy group promotes highly regioselective additions. The diene is known to react with amines, aldehydes, alkenes and alkynes.".
- Danishefskys_diene label "Danishefsky's diene".
- Danishefskys_diene sameAs Q904983.
- Danishefskys_diene sameAs Danishefsky-Dien.
- Danishefskys_diene sameAs ダニシェフスキージエン.
- Danishefskys_diene sameAs m.0h2p_5.
- Danishefskys_diene sameAs Danišefskijev_dien.
- Danishefskys_diene sameAs Danišefskijev_dien.
- Danishefskys_diene sameAs Q904983.
- Danishefskys_diene sameAs 丹尼謝夫斯基雙烯.
- Danishefskys_diene wasDerivedFrom Danishefskys_diene?oldid=668326165.
- Danishefskys_diene depiction Danishefsky-Diene_Structural_Formulae.png.
- Danishefskys_diene isPrimaryTopicOf Danishefskys_diene.