Sharpless epoxidation
E316986
Sharpless epoxidation is a landmark asymmetric oxidation reaction in organic chemistry that enables the enantioselective conversion of allylic alcohols to epoxides using chiral catalysts.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Sharpless epoxidation canonical | 5 |
How this entity was disambiguated
This entity first appeared as the object of triple T2974280 — 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: Sharpless epoxidation Context triple: [K. Barry Sharpless, notableWork, Sharpless epoxidation]
-
A.
The Logic of Chemical Synthesis
The Logic of Chemical Synthesis is a seminal book by chemist Elias J. Corey that systematically presents the principles and strategies of retrosynthetic analysis for designing complex organic molecule syntheses.
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B.
ChemCatChem
ChemCatChem is a peer-reviewed scientific journal focusing on catalysis research, including homogeneous, heterogeneous, and biocatalysis, published by Wiley-VCH.
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C.
Woodward–Hoffmann rules
The Woodward–Hoffmann rules are fundamental principles in organic chemistry that predict the stereochemistry and feasibility of pericyclic reactions based on orbital symmetry considerations.
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D.
“Superacids”
“Superacids” is a landmark chemistry book by George A. Olah that systematically explores extremely strong acids and their role in stabilizing carbocations and enabling unusual chemical reactions.
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E.
Beilstein
Beilstein is a small historic town in western Germany, known for its medieval architecture and picturesque setting in the Lahn region.
- 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: Sharpless epoxidation Target entity description: Sharpless epoxidation is a landmark asymmetric oxidation reaction in organic chemistry that enables the enantioselective conversion of allylic alcohols to epoxides using chiral catalysts.
-
A.
The Logic of Chemical Synthesis
The Logic of Chemical Synthesis is a seminal book by chemist Elias J. Corey that systematically presents the principles and strategies of retrosynthetic analysis for designing complex organic molecule syntheses.
-
B.
ChemCatChem
ChemCatChem is a peer-reviewed scientific journal focusing on catalysis research, including homogeneous, heterogeneous, and biocatalysis, published by Wiley-VCH.
-
C.
Woodward–Hoffmann rules
The Woodward–Hoffmann rules are fundamental principles in organic chemistry that predict the stereochemistry and feasibility of pericyclic reactions based on orbital symmetry considerations.
-
D.
“Superacids”
“Superacids” is a landmark chemistry book by George A. Olah that systematically explores extremely strong acids and their role in stabilizing carbocations and enabling unusual chemical reactions.
-
E.
Beilstein
Beilstein is a small historic town in western Germany, known for its medieval architecture and picturesque setting in the Lahn region.
- F. None of above. chosen
Statements (48)
| Predicate | Object |
|---|---|
| instanceOf |
asymmetric oxidation reaction
ⓘ
enantioselective synthesis method ⓘ named reaction in organic chemistry ⓘ |
| application |
construction of chiral building blocks
ⓘ
synthesis of natural products ⓘ synthesis of pharmaceuticals ⓘ |
| catalyst |
Ti(OiPr)4
ⓘ
titanium(IV) isopropoxide ⓘ |
| catalystType | chiral catalyst ⓘ |
| category |
asymmetric synthesis
ⓘ
organometallic catalysis ⓘ oxidation reactions ⓘ |
| developer | K. Barry Sharpless ⓘ |
| feature |
broad substrate scope for primary and secondary allylic alcohols
ⓘ
high enantioselectivity ⓘ mild reaction conditions ⓘ |
| field | organic chemistry ⓘ |
| ligand |
D-(−)-diethyl tartrate
ⓘ
L-(+)-diethyl tartrate ⓘ diethyl tartrate ⓘ |
| limitation |
not suitable for non-allylic alkenes
ⓘ
requires coordinating alcohol functionality ⓘ |
| mechanisticFeature |
epoxidation occurs via a concerted oxygen transfer
ⓘ
metal–tartrate complex activates tert-butyl hydroperoxide ⓘ |
| namedAfter | K. Barry Sharpless ⓘ |
| nobelLaureate | K. Barry Sharpless ⓘ |
| oxidant |
t-BuOOH
ⓘ
tert-butyl hydroperoxide ⓘ |
| product | chiral epoxides ⓘ |
| reactionType |
epoxidation
ⓘ
oxidation ⓘ |
| recognition | contributed to 2001 Nobel Prize in Chemistry ⓘ |
| relatedConcept |
asymmetric catalysis
ⓘ
enantioselective epoxidation ⓘ |
| relatedReaction |
Jacobsen epoxidation
ⓘ
Shi epoxidation ⓘ |
| requiresFunctionalGroup | free hydroxyl group on allylic alcohol ⓘ |
| selectivityControl |
allylic alcohol geometry influences stereochemical outcome
ⓘ
tartrate chirality controls epoxide configuration ⓘ |
| solvent |
CH2Cl2
ⓘ
dichloromethane ⓘ |
| stereochemicalControlElement | chiral titanium–tartrate complex ⓘ |
| stereochemicalOutcome |
asymmetric
ⓘ
enantioselective ⓘ |
| substrate | allylic alcohols ⓘ |
| temperature | low temperature ⓘ |
| typicalEnantiomericExcess | often greater than 90% ee ⓘ |
| yearDeveloped | 1970s ⓘ |
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: Sharpless epoxidation Description of subject: Sharpless epoxidation is a landmark asymmetric oxidation reaction in organic chemistry that enables the enantioselective conversion of allylic alcohols to epoxides using chiral catalysts.
Referenced by (5)
Full triples — surface form annotated when it differs from this entity's canonical label.