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- Ojima_lactam abstract "The Ojima lactam is an organic compound of some importance in the commercial production of Taxol. This lactam was first synthesized by Iwao Ojima. The organic synthesis is an illustration of asymmetric synthesis via a chiral auxiliary.The reaction centers around an imine - lithium enolate cycloaddition. In order to ensure the correct stereochemistry (the phenyl group and the silyl ether must adopt a cis configuration) in the β-lactam a chiral auxiliary is used in the enolate synthesis. The enolate synthesis starts from glycolic acid. The hydroxyl group is protected by a benzyl group and the carboxylic acid is activated by reaction with thionyl chloride to the acid chloride. The acid chloride reacts with the chiral auxiliary trans-2-phenyl-1-cyclohexanol. The benzyl group is then removed and replaced by a TES silyl ether by reaction with triethylsilyl chloride. Reaction with phenyllithium affords the enolate.The imine synthesis is a reaction of hexamethylene silazane with phenyllithium to a strong amide base followed by a condensation reaction with benzaldehyde.Both imine and enole intermediate join in a cycloaddition reaction followed by an intramolecular nucleophilic acyl substitution of the amine with expulsion of the chiral auxiliary to the cis-lactam. The triethylsilyl group is removed by hydrogen fluoride and the benzoyl group is added in a Schotten-Baumann reaction.".
- Ojima_lactam thumbnail OjimaTailPartI.svg?width=300.
- Ojima_lactam wikiPageID "11572922".
- Ojima_lactam wikiPageLength "2299".
- Ojima_lactam wikiPageOutDegree "44".
- Ojima_lactam wikiPageRevisionID "563957949".
- Ojima_lactam wikiPageWikiLink Acid_chloride.
- Ojima_lactam wikiPageWikiLink Acyl_chloride.
- Ojima_lactam wikiPageWikiLink Asymmetric_synthesis.
- Ojima_lactam wikiPageWikiLink Benzaldehyde.
- Ojima_lactam wikiPageWikiLink Benzyl.
- Ojima_lactam wikiPageWikiLink Carboxylic_acid.
- Ojima_lactam wikiPageWikiLink Category:Lactams.
- Ojima_lactam wikiPageWikiLink Chiral_auxiliary.
- Ojima_lactam wikiPageWikiLink Cis_configuration.
- Ojima_lactam wikiPageWikiLink Cis_isomer.
- Ojima_lactam wikiPageWikiLink Cis–trans_isomerism.
- Ojima_lactam wikiPageWikiLink Condensation_reaction.
- Ojima_lactam wikiPageWikiLink Cycloaddition.
- Ojima_lactam wikiPageWikiLink Enantioselective_synthesis.
- Ojima_lactam wikiPageWikiLink Enol.
- Ojima_lactam wikiPageWikiLink Enolate.
- Ojima_lactam wikiPageWikiLink Glycolic_acid.
- Ojima_lactam wikiPageWikiLink Hydrogen_fluoride.
- Ojima_lactam wikiPageWikiLink Hydroxyl.
- Ojima_lactam wikiPageWikiLink Imine.
- Ojima_lactam wikiPageWikiLink Intramolecular.
- Ojima_lactam wikiPageWikiLink Intramolecular_reaction.
- Ojima_lactam wikiPageWikiLink Iwao_Ojima.
- Ojima_lactam wikiPageWikiLink Lactam.
- Ojima_lactam wikiPageWikiLink Lithium.
- Ojima_lactam wikiPageWikiLink Nucleophilic_acyl_substitution.
- Ojima_lactam wikiPageWikiLink Organic_compound.
- Ojima_lactam wikiPageWikiLink Organic_synthesis.
- Ojima_lactam wikiPageWikiLink Organolithium_reagent.
- Ojima_lactam wikiPageWikiLink Paclitaxel_total_synthesis.
- Ojima_lactam wikiPageWikiLink Phenyl.
- Ojima_lactam wikiPageWikiLink Phenyl_group.
- Ojima_lactam wikiPageWikiLink Schotten-Baumann_reaction.
- Ojima_lactam wikiPageWikiLink Schotten–Baumann_reaction.
- Ojima_lactam wikiPageWikiLink Silazane.
- Ojima_lactam wikiPageWikiLink Silyl_ether.
- Ojima_lactam wikiPageWikiLink Stereochemistry.
- Ojima_lactam wikiPageWikiLink Taxol_total_synthesis.
- Ojima_lactam wikiPageWikiLink Thionyl_chloride.
- Ojima_lactam wikiPageWikiLink Trans-2-Phenyl-1-cyclohexanol.
- Ojima_lactam wikiPageWikiLink Trans-2-phenyl-1-cyclohexanol.
- Ojima_lactam wikiPageWikiLink Triethylsilyl_chloride.
- Ojima_lactam wikiPageWikiLink File:OjimaLactamPartII.svg.
- Ojima_lactam wikiPageWikiLink File:OjimaLactamPartIII.svg.
- Ojima_lactam wikiPageWikiLink File:OjimaTailPartI.svg.
- Ojima_lactam wikiPageWikiLinkText "Oijma chemistry".
- Ojima_lactam wikiPageWikiLinkText "Ojima chemistry".
- Ojima_lactam wikiPageWikiLinkText "Ojima lactam".
- Ojima_lactam hasPhotoCollection Ojima_lactam.
- Ojima_lactam wikiPageUsesTemplate Template:Reflist.
- Ojima_lactam subject Category:Lactams.
- Ojima_lactam hypernym Compound.
- Ojima_lactam type ChemicalCompound.
- Ojima_lactam type Amide.
- Ojima_lactam type Heterocycle.
- Ojima_lactam type Lactam.
- Ojima_lactam comment "The Ojima lactam is an organic compound of some importance in the commercial production of Taxol. This lactam was first synthesized by Iwao Ojima. The organic synthesis is an illustration of asymmetric synthesis via a chiral auxiliary.The reaction centers around an imine - lithium enolate cycloaddition. In order to ensure the correct stereochemistry (the phenyl group and the silyl ether must adopt a cis configuration) in the β-lactam a chiral auxiliary is used in the enolate synthesis.".
- Ojima_lactam label "Ojima lactam".
- Ojima_lactam sameAs m.03bxzj1.
- Ojima_lactam sameAs Q7081630.
- Ojima_lactam sameAs Q7081630.
- Ojima_lactam wasDerivedFrom Ojima_lactam?oldid=563957949.
- Ojima_lactam depiction OjimaTailPartI.svg.
- Ojima_lactam isPrimaryTopicOf Ojima_lactam.