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- Asymmetric_nucleophilic_epoxidation abstract "Nucleophilic epoxidation is the formation of epoxides from electron-deficient double bonds through the action of nucleophilic oxidants. Nucleophilic epoxidation methods represent a viable alternative to electrophilic methods, many of which do not epoxidize electron-poor double bonds efficiently.Although the most commonly used asymmetric epoxidation methods (the Sharpless-Katsuki, and Jacobsen epoxidations) rely on the catalytic reactivity of electrophilic oxidants, nucleophilic oxygen sources substituted with a suitable leaving group can also act as epoxidation reagents. The classic example, the Weitz-Scheffer reaction employs hydrogen peroxide under basic conditions (Z = OH below). Other notable examples have employed hypochlorites (Z = Cl) and chiral peroxides (Z = OR*).(1)File:NEpoxGen.pngAsymmetric versions of the above reaction have taken advantage of a number of strategies for achieving asymmetric induction. The highest yielding and most enantioselective methods include: Use of stoichiometric chiral oxidant Use of stoichiometric metal peroxides substituted with chiral ligands Use of stoichiometric chiral base Use of polypeptidesAlthough the mechanisms of each of these reactions differ somewhat, in each case the chiral catalyst or reagent must be involved in the enantio determining conjugate addition step. Cis-epoxides are difficult to access using nucleophilic epoxidation methods. Nearly all nucleophilic epoxidations of cis olefins afford trans epoxides.".
- Asymmetric_nucleophilic_epoxidation thumbnail NEpoxGen.png?width=300.
- Asymmetric_nucleophilic_epoxidation wikiPageExternalLink enantio-.
- Asymmetric_nucleophilic_epoxidation wikiPageID "27694210".
- Asymmetric_nucleophilic_epoxidation wikiPageLength "13785".
- Asymmetric_nucleophilic_epoxidation wikiPageOutDegree "45".
- Asymmetric_nucleophilic_epoxidation wikiPageRevisionID "602442825".
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink 1,1-Bi-2-naphthol.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Aldehyde.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Aldehydes.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Alkene.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Alkoxide.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink BINOL.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Catalysis.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Category:Organic_reactions.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Cinchona.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Cinnamates.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Cinnamic_acid.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Cumene_hydroperoxide.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Darzens_reaction.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Diethylzinc.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Double_bond.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Epoxidation.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Epoxide.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Ethane.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Hydrogen_peroxide.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Hydroperoxide.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Hypochlorite.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Hypochlorites.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Ligand.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Ligands.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Olefins.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Organic_peroxide.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Oxygen.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Parikh-Doering_oxidation.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Parikh–Doering_oxidation.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Peptide.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Peroxide.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Peroxides.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Phase-transfer_catalysis.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Phase-transfer_catalyst.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Polypeptides.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Sharpless_epoxidation.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Sodium_hypochlorite.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Stereoselectivity.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Swern_oxidation.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Trichloroisocyanuric_acid.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink Triphenylphosphine_oxide.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink File:NEpoxAlt1.png.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink File:NEpoxAlt2.png.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink File:NEpoxAlt3.png.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink File:NEpoxGen.png.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink File:NEpoxMech.png.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink File:NEpoxScope1.png.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink File:NEpoxScope2.png.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink File:NEpoxScope3.png.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink File:NEpoxScope4.png.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink File:NEpoxScope5.png.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink File:NEpoxScope6.png.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink File:NEpoxStereo1.png.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink File:NEpoxStereo2.png.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLink File:NEpoxStereo3.png.
- Asymmetric_nucleophilic_epoxidation wikiPageWikiLinkText "asymmetric nucleophilic epoxidation".
- Asymmetric_nucleophilic_epoxidation hasPhotoCollection Asymmetric_nucleophilic_epoxidation.
- Asymmetric_nucleophilic_epoxidation wikiPageUsesTemplate Template:Reflist.
- Asymmetric_nucleophilic_epoxidation subject Category:Organic_reactions.
- Asymmetric_nucleophilic_epoxidation hypernym Formation.
- Asymmetric_nucleophilic_epoxidation type Article.
- Asymmetric_nucleophilic_epoxidation type MilitaryUnit.
- Asymmetric_nucleophilic_epoxidation type Article.
- Asymmetric_nucleophilic_epoxidation type Reaction.
- Asymmetric_nucleophilic_epoxidation comment "Nucleophilic epoxidation is the formation of epoxides from electron-deficient double bonds through the action of nucleophilic oxidants.".
- Asymmetric_nucleophilic_epoxidation label "Asymmetric nucleophilic epoxidation".
- Asymmetric_nucleophilic_epoxidation sameAs m.0ds8mpl.
- Asymmetric_nucleophilic_epoxidation sameAs Q4812081.
- Asymmetric_nucleophilic_epoxidation sameAs Q4812081.
- Asymmetric_nucleophilic_epoxidation wasDerivedFrom Asymmetric_nucleophilic_epoxidation?oldid=602442825.
- Asymmetric_nucleophilic_epoxidation depiction NEpoxGen.png.
- Asymmetric_nucleophilic_epoxidation isPrimaryTopicOf Asymmetric_nucleophilic_epoxidation.