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- Aza-Baylis–Hillman_reaction abstract "The aza-Baylis–Hillman reaction or aza-BH reaction in organic chemistry is a variation of the Baylis–Hillman reaction and describes the reaction of an electron deficient alkene usually an α,β-unsaturated carbonyl compound with an imine in the presence of a nucleophile. The reaction product is an allylic amine. The reaction can be carried out in enantiomeric excess of up to 90% with the aid of bifunctional chiral BINOL and phosphinyl BINOL compounds, for example in the reaction of n-(4-chloro-benzylidene)-benzenesulfonamide with methyl vinyl ketone (MVK) in cyclopentyl methyl ether and toluene at -15°C.In one study a reaction mechanism for a specific aza-BH reaction is proposed. Given a set of reaction conditions the reaction is found to be first-order in the triphenylphosphine nucleophile, MVK and the tosylimine concentration in the rate determining step in the presence of a Brønsted acid such as phenol or benzoic acid. The presence of an acid facilitates the elimination reaction in the zwitterion by proton transfer which becomes much faster and no longer rate determining. A 6 membered cyclic transition state is proposed for this reaction step. Because this step is also reversible the presence of acid causes a racemisation process simply by mixing chiral aza-BH adduct, phosphine and acid. Aza-Baylis–Hillman reaction, Ph stands for a phenyl group↑ ↑".
- Aza-Baylis–Hillman_reaction thumbnail ABHreaction.png?width=300.
- Aza-Baylis–Hillman_reaction wikiPageExternalLink 30JanuaryA.shtm.
- Aza-Baylis–Hillman_reaction wikiPageID "3343173".
- Aza-Baylis–Hillman_reaction wikiPageLength "4104".
- Aza-Baylis–Hillman_reaction wikiPageOutDegree "45".
- Aza-Baylis–Hillman_reaction wikiPageRevisionID "703669591".
- Aza-Baylis–Hillman_reaction wikiPageWikiLink 1,1-Bi-2-naphthol.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Alkene.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Allyl.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Amine.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Ammonium.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink BINAP.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Baylis–Hillman_reaction.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Benzoic_acid.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Boric_acid.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Brønsted–Lowry_acid–base_theory.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Carbonyl.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Category:Addition_reactions.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Category:Carbon-carbon_bond_forming_reactions.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Category:Name_reactions.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Chiral_ligand.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Chiral_pool_synthesis.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Chirality_(chemistry).
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Elimination_reaction.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Enantiomeric_excess.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Enantioselective_synthesis.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Imine.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Ionic_liquid.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Malic_acid.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Melting_point.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Methyl_vinyl_ketone.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Nucleophile.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Order_of_reaction.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Organic_chemistry.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Phenol.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Racemization.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Rate-determining_step.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Reaction_mechanism.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Reversible_reaction.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Sodium_hydroxide.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Toluene.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Transition_state.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Triphenylphosphine.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Yield_(chemistry).
- Aza-Baylis–Hillman_reaction wikiPageWikiLink Zwitterion.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink File:ABHreaction.png.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink File:ChiralSolventForAzizBHreaction.png.
- Aza-Baylis–Hillman_reaction wikiPageWikiLink File:Chiral_aza_BH.png.
- Aza-Baylis–Hillman_reaction wikiPageWikiLinkText "Aza-Baylis–Hillman reaction".
- Aza-Baylis–Hillman_reaction wikiPageWikiLinkText "aza-Baylis–Hillman reaction".
- Aza-Baylis–Hillman_reaction name "Aza-Baylis-Hillman reaction".
- Aza-Baylis–Hillman_reaction namedafter "Anthony B. Baylis".
- Aza-Baylis–Hillman_reaction namedafter "Melville E. D. Hillman".
- Aza-Baylis–Hillman_reaction type "Coupling reaction".
- Aza-Baylis–Hillman_reaction wikiPageUsesTemplate Template:Reactionbox.
- Aza-Baylis–Hillman_reaction wikiPageUsesTemplate Template:Reactionbox_Identifiers.
- Aza-Baylis–Hillman_reaction subject Category:Addition_reactions.
- Aza-Baylis–Hillman_reaction subject Category:Carbon-carbon_bond_forming_reactions.
- Aza-Baylis–Hillman_reaction subject Category:Name_reactions.
- Aza-Baylis–Hillman_reaction hypernym Variation.
- Aza-Baylis–Hillman_reaction type Food.
- Aza-Baylis–Hillman_reaction type Eponym.
- Aza-Baylis–Hillman_reaction type Reaction.
- Aza-Baylis–Hillman_reaction type Redirect.
- Aza-Baylis–Hillman_reaction comment "The aza-Baylis–Hillman reaction or aza-BH reaction in organic chemistry is a variation of the Baylis–Hillman reaction and describes the reaction of an electron deficient alkene usually an α,β-unsaturated carbonyl compound with an imine in the presence of a nucleophile. The reaction product is an allylic amine.".
- Aza-Baylis–Hillman_reaction label "Aza-Baylis–Hillman reaction".
- Aza-Baylis–Hillman_reaction sameAs Q4831993.
- Aza-Baylis–Hillman_reaction sameAs m.096tf7.
- Aza-Baylis–Hillman_reaction sameAs Q4831993.
- Aza-Baylis–Hillman_reaction wasDerivedFrom Aza-Baylis–Hillman_reaction?oldid=703669591.
- Aza-Baylis–Hillman_reaction depiction ABHreaction.png.
- Aza-Baylis–Hillman_reaction isPrimaryTopicOf Aza-Baylis–Hillman_reaction.