Stork enamine reaction
E683997
The Stork enamine reaction is a key carbon–carbon bond-forming method in organic chemistry that uses enamines as nucleophiles to alkylate or acylate carbonyl compounds in a controlled, selective way.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Stork enamine reaction canonical | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T7731592 — 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.
NED1
Entity disambiguation (via context triple)
gpt-5-mini-2025-08-07
Target entity: Stork enamine reaction Context triple: [Gilbert Stork, knownFor, Stork enamine reaction]
-
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–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.
-
C.
Robinson annulation reaction
The Robinson annulation reaction is a classic organic chemistry transformation that forms six-membered rings by combining a Michael addition with an intramolecular aldol condensation, widely used in the synthesis of complex cyclic molecules and natural products.
-
D.
Buchwald–Hartwig amination
The Buchwald–Hartwig amination is a palladium-catalyzed cross-coupling reaction that forms carbon–nitrogen bonds by coupling aryl (or vinyl) halides with amines, widely used in the synthesis of pharmaceuticals and fine chemicals.
-
E.
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.
- F. None of above. chosen
- G. Unsure - the case is ambiguous/there is not enough information to decide.
NED2
Entity disambiguation (via description)
gpt-5-mini-2025-08-07
Target entity: Stork enamine reaction Target entity description: The Stork enamine reaction is a key carbon–carbon bond-forming method in organic chemistry that uses enamines as nucleophiles to alkylate or acylate carbonyl compounds in a controlled, selective way.
-
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–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.
-
C.
Robinson annulation reaction
The Robinson annulation reaction is a classic organic chemistry transformation that forms six-membered rings by combining a Michael addition with an intramolecular aldol condensation, widely used in the synthesis of complex cyclic molecules and natural products.
-
D.
Buchwald–Hartwig amination
The Buchwald–Hartwig amination is a palladium-catalyzed cross-coupling reaction that forms carbon–nitrogen bonds by coupling aryl (or vinyl) halides with amines, widely used in the synthesis of pharmaceuticals and fine chemicals.
-
E.
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.
- F. None of above. chosen
Statements (49)
| Predicate | Object |
|---|---|
| instanceOf |
carbon–carbon bond-forming reaction
ⓘ
named reaction ⓘ organic reaction ⓘ |
| advantage |
avoids strong base required for direct enolate alkylation
ⓘ
compatible with base-sensitive functional groups ⓘ provides controlled monoalkylation ⓘ |
| bondFormed | carbon–carbon single bond ⓘ |
| category |
C–C bond formation
ⓘ
α-functionalization of carbonyl compounds ⓘ |
| developedBy | Gilbert Stork NERFINISHED ⓘ |
| field | organic chemistry ⓘ |
| hasElectrophile |
acid anhydride
ⓘ
activated carbonyl compound ⓘ acyl halide ⓘ alkyl halide ⓘ |
| hasNucleophile | enamine ⓘ |
| mechanismType | stepwise ⓘ |
| mechanisticStep |
enamine formation
ⓘ
iminium ion hydrolysis ⓘ nucleophilic acyl substitution ⓘ nucleophilic substitution ⓘ |
| namedAfter | Gilbert Stork NERFINISHED ⓘ |
| produces |
α-acylated carbonyl compound
ⓘ
α-alkylated carbonyl compound ⓘ α-substituted carbonyl compound ⓘ |
| reactionCenter | α-carbon of carbonyl compound ⓘ |
| reactivityControl | enamine nucleophilicity at α-carbon ⓘ |
| relatedTo |
Mannich reaction
NERFINISHED
ⓘ
acetoacetic ester synthesis NERFINISHED ⓘ enolate chemistry ⓘ |
| requires | formation of an enamine precursor ⓘ |
| selectivity |
often stereoselective
ⓘ
α-regioselective ⓘ |
| solvent |
aprotic solvent
ⓘ
polar solvent ⓘ |
| typicalElectrophileClass |
activated secondary alkyl halide
ⓘ
primary alkyl halide ⓘ |
| typicalEnamineSource |
aldehyde
ⓘ
ketone ⓘ secondary amine ⓘ |
| usedIn |
complex molecule synthesis
ⓘ
natural product synthesis ⓘ pharmaceutical synthesis ⓘ |
| usesReagent |
acid anhydride
ⓘ
acyl halide ⓘ alkyl halide ⓘ carbonyl compound ⓘ enamine ⓘ |
| workup | aqueous acid hydrolysis ⓘ |
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.
Instruction
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.
Input
Subject: Stork enamine reaction Description of subject: The Stork enamine reaction is a key carbon–carbon bond-forming method in organic chemistry that uses enamines as nucleophiles to alkylate or acylate carbonyl compounds in a controlled, selective way.
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.