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- Aza-Diels–Alder_reaction abstract "The aza-Diels–Alder reaction converts imines and dienes to tetrahydropyridines. This organic reaction is a modification of the Diels–Alder reaction. The nitrogen atom can be part of the diene or the dienophile.The imine is often generated in situ from an amine and formaldehyde. An example is the reaction of cyclopentadiene with benzylamine to an aza norbornene.In the enantioselective Diels–Alder (DA) reaction of an aniline, formaldehyde and a cyclohexenone catalyzed by (S)-proline even the diene is masked.The catalytic cycle starts with the reactions of the aromatic amine with formaldehyde to the imine and the reaction of the ketone with proline to the diene. The second step, an endo trig cyclisation, is driven to one of the two possible enantiomers (99% ee) because the imine nitrogen atom forms a hydrogen bond with the carboxylic acid group of proline on the Si face. Hydrolysis of the final complex releases the product and regenerates the catalyst.In 2014, Doyle and coworkers reported a Zn(OTf)2-catalyzed [4+2] cycloaddition reaction between two imines to form tetrahydropyrimidine products.".
- Aza-Diels–Alder_reaction thumbnail Aza_Diels_Alder.gif?width=300.
- Aza-Diels–Alder_reaction wikiPageID "2342852".
- Aza-Diels–Alder_reaction wikiPageLength "2422".
- Aza-Diels–Alder_reaction wikiPageOutDegree "38".
- Aza-Diels–Alder_reaction wikiPageRevisionID "631221064".
- Aza-Diels–Alder_reaction wikiPageWikiLink Amine.
- Aza-Diels–Alder_reaction wikiPageWikiLink Aniline.
- Aza-Diels–Alder_reaction wikiPageWikiLink Baldwins_rules.
- Aza-Diels–Alder_reaction wikiPageWikiLink Benzylamine.
- Aza-Diels–Alder_reaction wikiPageWikiLink Cahn–Ingold–Prelog_priority_rules.
- Aza-Diels–Alder_reaction wikiPageWikiLink Carboxylic_acid.
- Aza-Diels–Alder_reaction wikiPageWikiLink Catalysis.
- Aza-Diels–Alder_reaction wikiPageWikiLink Catalytic_cycle.
- Aza-Diels–Alder_reaction wikiPageWikiLink Category:Cycloadditions.
- Aza-Diels–Alder_reaction wikiPageWikiLink Category:Heterocycle_forming_reactions.
- Aza-Diels–Alder_reaction wikiPageWikiLink Category:Name_reactions.
- Aza-Diels–Alder_reaction wikiPageWikiLink Cyclohexenone.
- Aza-Diels–Alder_reaction wikiPageWikiLink Cyclopentadiene.
- Aza-Diels–Alder_reaction wikiPageWikiLink Diels–Alder_reaction.
- Aza-Diels–Alder_reaction wikiPageWikiLink Diene.
- Aza-Diels–Alder_reaction wikiPageWikiLink Enantiomer.
- Aza-Diels–Alder_reaction wikiPageWikiLink Enantiomeric_excess.
- Aza-Diels–Alder_reaction wikiPageWikiLink Formaldehyde.
- Aza-Diels–Alder_reaction wikiPageWikiLink Hydrogen_bond.
- Aza-Diels–Alder_reaction wikiPageWikiLink Imine.
- Aza-Diels–Alder_reaction wikiPageWikiLink In_situ.
- Aza-Diels–Alder_reaction wikiPageWikiLink Ketone.
- Aza-Diels–Alder_reaction wikiPageWikiLink Norbornene.
- Aza-Diels–Alder_reaction wikiPageWikiLink Organic_reaction.
- Aza-Diels–Alder_reaction wikiPageWikiLink Oxo-Diels–Alder_reaction.
- Aza-Diels–Alder_reaction wikiPageWikiLink Proline.
- Aza-Diels–Alder_reaction wikiPageWikiLink Tetrahydropyridine.
- Aza-Diels–Alder_reaction wikiPageWikiLink File:Aza-Diels-Alder_phenylmethylamine.gif.
- Aza-Diels–Alder_reaction wikiPageWikiLink File:Aza_DA_mechanism.gif.
- Aza-Diels–Alder_reaction wikiPageWikiLink File:Aza_Diels_Alder.gif.
- Aza-Diels–Alder_reaction wikiPageWikiLink File:Aza_Diels_Alder_proline.gif.
- Aza-Diels–Alder_reaction wikiPageWikiLinkText "Aza-Diels–Alder reaction".
- Aza-Diels–Alder_reaction wikiPageWikiLinkText "aza-Diels–Alder reaction".
- Aza-Diels–Alder_reaction wikiPageWikiLinkText "aza-Diels–Alder".
- Aza-Diels–Alder_reaction subject Category:Cycloadditions.
- Aza-Diels–Alder_reaction subject Category:Heterocycle_forming_reactions.
- Aza-Diels–Alder_reaction subject Category:Name_reactions.
- Aza-Diels–Alder_reaction type Eponym.
- Aza-Diels–Alder_reaction type Reaction.
- Aza-Diels–Alder_reaction comment "The aza-Diels–Alder reaction converts imines and dienes to tetrahydropyridines. This organic reaction is a modification of the Diels–Alder reaction. The nitrogen atom can be part of the diene or the dienophile.The imine is often generated in situ from an amine and formaldehyde.".
- Aza-Diels–Alder_reaction label "Aza-Diels–Alder reaction".
- Aza-Diels–Alder_reaction sameAs Q2042393.
- Aza-Diels–Alder_reaction sameAs Aza-Diels-Alder-reactie.
- Aza-Diels–Alder_reaction sameAs m.0754h4.
- Aza-Diels–Alder_reaction sameAs Q2042393.
- Aza-Diels–Alder_reaction sameAs 氮杂双烯狄尔斯–阿尔德反应.
- Aza-Diels–Alder_reaction wasDerivedFrom Aza-Diels–Alder_reaction?oldid=631221064.
- Aza-Diels–Alder_reaction depiction Aza_Diels_Alder.gif.
- Aza-Diels–Alder_reaction isPrimaryTopicOf Aza-Diels–Alder_reaction.