Sharpless asymmetric dihydroxylation
E316987
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.
All labels observed (2)
| Label | Occurrences |
|---|---|
| Sharpless asymmetric dihydroxylation canonical | 3 |
| Sharpless dihydroxylation | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T2974281 — 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 asymmetric dihydroxylation Context triple: [K. Barry Sharpless, notableWork, Sharpless asymmetric dihydroxylation]
-
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.
ACS Catalysis
ACS Catalysis is a peer-reviewed scientific journal focusing on cutting-edge research in catalysis across chemistry, biology, and engineering.
- 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 asymmetric dihydroxylation Target entity description: 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.
-
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.
ACS Catalysis
ACS Catalysis is a peer-reviewed scientific journal focusing on cutting-edge research in catalysis across chemistry, biology, and engineering.
- F. None of above. chosen
Statements (48)
| Predicate | Object |
|---|---|
| instanceOf |
asymmetric catalytic reaction
ⓘ
chemical reaction ⓘ name reaction ⓘ oxidation reaction ⓘ |
| addsFunctionalGroup | hydroxyl group ⓘ |
| addsNumberOfHydroxylGroups | 2 ⓘ |
| application |
pharmaceutical synthesis
ⓘ
synthesis of chiral building blocks ⓘ total synthesis of natural products ⓘ |
| awardRelatedTo | Nobel Prize in Chemistry 2001 ⓘ |
| commercialFormulation |
AD-mix-α
ⓘ
AD-mix-β ⓘ |
| contributedTo | development of asymmetric catalysis ⓘ |
| developedBy | K. Barry Sharpless ⓘ |
| developedInDecade | 1980s ⓘ |
| field |
asymmetric synthesis
ⓘ
organic chemistry ⓘ |
| impact | revolutionized asymmetric synthesis in organic chemistry ⓘ |
| ligandFamily |
(DHQ)2PHAL
ⓘ
(DHQD)2PHAL ⓘ |
| limitation | uses toxic osmium tetroxide ⓘ |
| mechanismFeature |
formation of cyclic osmate ester intermediate
ⓘ
osmium(VIII)–osmium(VI) catalytic cycle ⓘ |
| namedAfter | K. Barry Sharpless ⓘ |
| product |
1,2-diol
ⓘ
vicinal diol ⓘ |
| property |
catalytic in osmium
ⓘ
high enantioselectivity ⓘ high regioselectivity ⓘ |
| reactant |
alkene
ⓘ
olefin ⓘ |
| selectivityControlledBy | chiral ligand configuration ⓘ |
| stereochemicalOutcome | syn addition ⓘ |
| stereocontrolType | ligand-controlled ⓘ |
| typicalBase | potassium carbonate ⓘ |
| typicalOxidant | potassium ferricyanide ⓘ |
| uses |
AD-mix-α
ⓘ
AD-mix-β ⓘ OsO4 ⓘ chiral catalyst ⓘ chiral ligand ⓘ cinchona alkaloid–derived ligands ⓘ co-oxidant ⓘ osmium tetroxide ⓘ potassium ferricyanide ⓘ tert-butanol–water solvent mixture ⓘ |
| worksBestOn | terminal alkenes ⓘ |
| worksOn | disubstituted alkenes ⓘ |
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 asymmetric dihydroxylation Description of subject: 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.
Referenced by (4)
Full triples — surface form annotated when it differs from this entity's canonical label.