Breslow intermediate in organocatalysis
E601249
The Breslow intermediate in organocatalysis is a transient nucleophilic carbene-derived species central to thiamine- and N-heterocyclic carbene-catalyzed umpolung reactions of carbonyl compounds.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Breslow intermediate in organocatalysis canonical | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T6630411 — resolving that mention is where its identity was fixed. The disambiguator weighed these candidate entities and picked the highlighted one (or “None”, minting a new entity). This is how homonymy is resolved: the same surface form can point to different entities.
Target entity: Breslow intermediate in organocatalysis Context triple: [Ronald Breslow, knownFor, Breslow intermediate in organocatalysis]
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A.
Eschenmoser sulfide contraction
Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
-
B.
Corey–Winter olefin synthesis
Corey–Winter olefin synthesis is an organic reaction that converts 1,2-diols into alkenes via cyclic thiocarbonate intermediates, widely used for stereospecific formation of double bonds.
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C.
Corey–Nicolaou macrolactonization
Corey–Nicolaou macrolactonization is a widely used organic synthesis reaction that forms large-ring lactones from hydroxy acids via an activated ester intermediate.
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D.
Sharpless asymmetric dihydroxylation
Sharpless asymmetric dihydroxylation is a landmark chemical reaction that uses chiral catalysts to add two hydroxyl groups across an alkene with high enantioselectivity, revolutionizing asymmetric synthesis in organic chemistry.
-
E.
Trost asymmetric allylic alkylation
Trost asymmetric allylic alkylation is a palladium-catalyzed enantioselective carbon–carbon bond-forming reaction that enables the synthesis of chiral molecules from prochiral allylic substrates.
- F. None of above. chosen
- G. Unsure - the case is ambiguous/there is not enough information to decide.
Target entity: Breslow intermediate in organocatalysis Target entity description: The Breslow intermediate in organocatalysis is a transient nucleophilic carbene-derived species central to thiamine- and N-heterocyclic carbene-catalyzed umpolung reactions of carbonyl compounds.
-
A.
Eschenmoser sulfide contraction
Eschenmoser sulfide contraction is an organic rearrangement reaction that converts certain sulfur-containing intermediates into carbonyl compounds, widely used in complex molecule and natural product synthesis.
-
B.
Corey–Winter olefin synthesis
Corey–Winter olefin synthesis is an organic reaction that converts 1,2-diols into alkenes via cyclic thiocarbonate intermediates, widely used for stereospecific formation of double bonds.
-
C.
Corey–Nicolaou macrolactonization
Corey–Nicolaou macrolactonization is a widely used organic synthesis reaction that forms large-ring lactones from hydroxy acids via an activated ester intermediate.
-
D.
Sharpless asymmetric dihydroxylation
Sharpless asymmetric dihydroxylation is a landmark chemical reaction that uses chiral catalysts to add two hydroxyl groups across an alkene with high enantioselectivity, revolutionizing asymmetric synthesis in organic chemistry.
-
E.
Trost asymmetric allylic alkylation
Trost asymmetric allylic alkylation is a palladium-catalyzed enantioselective carbon–carbon bond-forming reaction that enables the synthesis of chiral molecules from prochiral allylic substrates.
- F. None of above. chosen
Statements (46)
| Predicate | Object |
|---|---|
| instanceOf |
carbene-derived species
ⓘ
nucleophilic carbene intermediate ⓘ reaction intermediate ⓘ |
| enables | nucleophilic reactivity at the former carbonyl carbon ⓘ |
| hasBeen | characterized by spectroscopic methods in some systems ⓘ |
| hasChemicalNature |
carbene-derived
ⓘ
nucleophilic ⓘ |
| hasElectronicCharacter |
acyl anion equivalent
ⓘ
enaminol-like ⓘ zwitterionic ⓘ |
| hasFunctionalGroupFeatures |
alpha-hydroxyalkyl substituent on carbene center
ⓘ
conjugated C=C–O system ⓘ |
| hasPrecursor |
N-heterocyclic carbene catalyst
ⓘ
aldehyde substrate ⓘ carbonyl compound ⓘ thiamine-derived carbene ⓘ |
| hasRole |
key intermediate in organocatalysis
ⓘ
umpolung reagent ⓘ |
| hasStability | short-lived ⓘ |
| isAssociatedWith |
biomimetic NHC catalysis
ⓘ
thiamine pyrophosphate catalysis ⓘ |
| isCentralTo |
N-heterocyclic carbene-catalyzed umpolung reactions
ⓘ
thiamine-catalyzed umpolung reactions ⓘ |
| isDerivedFrom |
N-heterocyclic carbene
ⓘ
thiazolium carbene ⓘ |
| isDifficultTo | isolate ⓘ |
| isDiscussedIn |
organocatalysis literature
ⓘ
physical organic chemistry of carbenes ⓘ |
| isFormedBy |
addition of carbene to carbonyl carbon
ⓘ
proton transfer from carbonyl carbon to carbene center ⓘ |
| isImportantFor |
design of NHC catalysts
ⓘ
understanding thiamine-dependent enzymatic mechanisms ⓘ |
| isKeyTo | reversal of polarity at the carbonyl carbon ⓘ |
| isNamedAfter | Ronald Breslow NERFINISHED ⓘ |
| isOften | observed indirectly ⓘ |
| isTransient | true ⓘ |
| isUsedIn |
organocatalytic C–C bond formation
ⓘ
organocatalytic acylation reactions ⓘ |
| participatesIn |
NHC-catalyzed acyl anion equivalent chemistry
ⓘ
Stetter reaction NERFINISHED ⓘ benzoin condensation ⓘ umpolung of carbonyl compounds ⓘ |
| reactsWith |
Michael acceptors
ⓘ
electrophilic carbonyl compounds ⓘ |
| wasProposedBy | Ronald Breslow NERFINISHED ⓘ |
| wasProposedIn | 1958 ⓘ |
How these facts were elicited
The pipeline generated the facts above by prompting gpt-5.1 with this entity's name + description and the instruction below.
You are a knowledge base construction expert. Given a subject entity and a description of it, return factual statements that you know for the subject as a JSON list of dictionaries(triples), where keys must be "subject", "predicate" and "object". The number of facts may be very high, between 25 to 50 or more, for very popular subjects. For less popular subjects, the number of facts can be very low, like 5 or 10. # Requirements - If you don't know the subject at all, return an empty list. - If the subject is not a named entity, return an empty list. - Include at least one triple where predicate is "instanceOf". - Do not get too wordy. - Separate several objects into multiple triples with one object.
Subject: Breslow intermediate in organocatalysis Description of subject: The Breslow intermediate in organocatalysis is a transient nucleophilic carbene-derived species central to thiamine- and N-heterocyclic carbene-catalyzed umpolung reactions of carbonyl compounds.
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.