Corey–Winter olefin synthesis
E466668
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.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Corey–Winter olefin synthesis canonical | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T4741218 — 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: Corey–Winter olefin synthesis Context triple: [E. J. Corey, developedMethod, Corey–Winter olefin synthesis]
-
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.
Barton–McCombie deoxygenation
Barton–McCombie deoxygenation is an organic chemistry reaction that converts alcohols into the corresponding hydrocarbons via radical-mediated removal of the hydroxyl group.
-
C.
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.
-
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.
Sharpless epoxidation
Sharpless epoxidation is a landmark asymmetric oxidation reaction in organic chemistry that enables the enantioselective conversion of allylic alcohols to epoxides using chiral catalysts.
- 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: Corey–Winter olefin synthesis Target entity description: 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.
-
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.
Barton–McCombie deoxygenation
Barton–McCombie deoxygenation is an organic chemistry reaction that converts alcohols into the corresponding hydrocarbons via radical-mediated removal of the hydroxyl group.
-
C.
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.
-
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.
Sharpless epoxidation
Sharpless epoxidation is a landmark asymmetric oxidation reaction in organic chemistry that enables the enantioselective conversion of allylic alcohols to epoxides using chiral catalysts.
- F. None of above. chosen
Statements (47)
| Predicate | Object |
|---|---|
| instanceOf |
named reaction
ⓘ
olefination reaction ⓘ organic reaction ⓘ |
| advantage |
avoids strong acidic conditions
ⓘ
preserves stereochemistry of starting diol ⓘ |
| application |
construction of defined alkene geometry
ⓘ
stereospecific formation of double bonds ⓘ synthesis of complex natural products ⓘ |
| bondChange |
C=C bond formation
ⓘ
C–O bond cleavage ⓘ |
| classification | two-step transformation via isolable intermediate ⓘ |
| commonUseCase |
conversion of acyclic 1,2-diols to acyclic alkenes
ⓘ
conversion of cyclic 1,2-diols to cycloalkenes ⓘ |
| converts | 1,2-diols ⓘ |
| developedBy |
E. J. Corey
ⓘ
S. Winter ⓘ |
| field | organic chemistry ⓘ |
| intermediateType | cyclic thiocarbonate ester ⓘ |
| keyIntermediate | cyclic thiocarbonate ⓘ |
| limitation |
best suited to 5-membered cyclic thiocarbonates
ⓘ
requires formation of cyclic thiocarbonate ⓘ |
| mechanismFeature |
elimination of carbonyl sulfide or related species
ⓘ
phosphite-induced fragmentation ⓘ |
| mechanisticStep |
formation of cyclic thiocarbonate from 1,2-diol
ⓘ
fragmentation of cyclic thiocarbonate to alkene ⓘ |
| naming | named after E. J. Corey and S. Winter ⓘ |
| produces | alkenes ⓘ |
| productGeometryControl | alkene geometry dictated by diol configuration ⓘ |
| reactionCondition | often performed under mild conditions ⓘ |
| reactionType | deoxygenation ⓘ |
| relatedTo |
dehydration of diols
ⓘ
olefination reactions ⓘ |
| selectivity | high stereoselectivity for E or Z alkene depending on diol geometry ⓘ |
| stereochemicalOutcome |
retention of relative configuration of the diol
ⓘ
stereospecific ⓘ |
| substrateRequirement |
neighboring hydroxyl groups
ⓘ
vicinal diol configuration ⓘ |
| typicalProduct | disubstituted alkene ⓘ |
| typicalStartingMaterial |
1,2-diol
ⓘ
vicinal diol ⓘ |
| usedIn |
laboratory organic synthesis
ⓘ
stereocontrolled synthesis of alkenes ⓘ |
| usesReagent |
phosgene equivalents
ⓘ
thiocarbonyldiimidazole ⓘ thiophosgene ⓘ trialkyl phosphite ⓘ trimethyl phosphite ⓘ |
How these facts were elicited
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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: Corey–Winter olefin synthesis Description of subject: 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.
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.