Shi epoxidation
E1032134
Shi epoxidation is an asymmetric organocatalytic reaction that converts alkenes to chiral epoxides using a fructose-derived ketone catalyst and an oxidant such as oxone.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Shi epoxidation canonical | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T13308047 — 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: Shi epoxidation Context triple: [Sharpless epoxidation, relatedReaction, Shi epoxidation]
-
A.
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.
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B.
Corey–Kim oxidation
Corey–Kim oxidation is an organic chemistry reaction that converts primary and secondary alcohols into aldehydes and ketones using N-chlorosuccinimide and dimethyl sulfide under mild conditions.
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C.
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.
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D.
Barton reaction
The Barton reaction is an organic photochemical transformation that converts nitrite esters into δ-nitroso alcohols via intramolecular hydrogen abstraction and radical rearrangement.
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E.
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.
- 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: Shi epoxidation Target entity description: Shi epoxidation is an asymmetric organocatalytic reaction that converts alkenes to chiral epoxides using a fructose-derived ketone catalyst and an oxidant such as oxone.
-
A.
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.
-
B.
Corey–Kim oxidation
Corey–Kim oxidation is an organic chemistry reaction that converts primary and secondary alcohols into aldehydes and ketones using N-chlorosuccinimide and dimethyl sulfide under mild conditions.
-
C.
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.
-
D.
Barton reaction
The Barton reaction is an organic photochemical transformation that converts nitrite esters into δ-nitroso alcohols via intramolecular hydrogen abstraction and radical rearrangement.
-
E.
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.
- F. None of above. chosen
Statements (47)
| Predicate | Object |
|---|---|
| instanceOf |
asymmetric epoxidation
ⓘ
organic reaction ⓘ organocatalytic reaction ⓘ oxidation reaction ⓘ |
| advantage |
high enantioselectivity
ⓘ
metal-free catalysis ⓘ use of inexpensive oxidant ⓘ |
| appliesTo |
conjugated alkenes
ⓘ
electron-rich alkenes ⓘ styrene derivatives ⓘ |
| catalystClass | chiral dioxirane precursor ⓘ |
| catalystOrigin |
carbohydrate-derived ketone
ⓘ
fructose-derived chiral scaffold ⓘ |
| catalystRole | induces chirality in epoxide product ⓘ |
| comparedTo |
Jacobsen–Katsuki epoxidation
ⓘ
Sharpless epoxidation ⓘ |
| developedBy | Yian Shi ⓘ |
| field |
asymmetric synthesis
ⓘ
organocatalysis ⓘ |
| goal | synthesis of optically active epoxides ⓘ |
| hasSubstrate | alkenes ⓘ |
| mechanismFeature |
dioxirane intermediate
ⓘ
in situ generated dioxirane oxidant ⓘ |
| namedAfter | Yian Shi ⓘ |
| notableFeature | organocatalytic alternative to metal-based epoxidations ⓘ |
| oxidantClass | peroxymonosulfate-based oxidant ⓘ |
| oxidantRole | generates dioxirane from ketone catalyst ⓘ |
| produces | chiral epoxides ⓘ |
| productType | epoxides with defined absolute configuration ⓘ |
| reactionCondition |
aqueous conditions
ⓘ
mild temperatures ⓘ |
| reactionMedium |
aqueous organic solvent mixture
ⓘ
biphasic system ⓘ |
| reactionStep |
oxidation of chiral ketone to dioxirane
ⓘ
oxygen transfer from dioxirane to alkene ⓘ |
| reactionType | enantioselective epoxidation ⓘ |
| selectivityType |
diastereoselective
ⓘ
enantioselective ⓘ |
| stereocontrolSource | chiral ketone catalyst ⓘ |
| usedIn |
pharmaceutical synthesis
ⓘ
total synthesis of natural products ⓘ |
| usesAdditive |
buffer
ⓘ
phase-transfer agent ⓘ |
| usesCatalyst |
chiral ketone catalyst
ⓘ
fructose-derived ketone ⓘ |
| usesOxidant |
oxone
ⓘ
potassium peroxymonosulfate ⓘ |
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: Shi epoxidation Description of subject: Shi epoxidation is an asymmetric organocatalytic reaction that converts alkenes to chiral epoxides using a fructose-derived ketone catalyst and an oxidant such as oxone.
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.