Sharpless aminohydroxylation
E316988
Sharpless aminohydroxylation is a stereoselective chemical reaction that converts alkenes into vicinal amino alcohols using a chiral catalyst, widely used in asymmetric synthesis.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Sharpless aminohydroxylation canonical | 2 |
How this entity was disambiguated
This entity first appeared as the object of triple T2974282 — 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 aminohydroxylation Context triple: [K. Barry Sharpless, notableWork, Sharpless aminohydroxylation]
-
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.
“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.
-
C.
New Organon
New Organon is a foundational philosophical work by Francis Bacon that proposes a new method of scientific inquiry based on empirical observation and inductive reasoning.
-
D.
CYP2J2
CYP2J2 is a human cytochrome P450 enzyme primarily expressed in the heart and other tissues, involved in the metabolism of various drugs and endogenous fatty acids.
-
E.
Lextran
Lextran is the public bus transit system serving Lexington and surrounding areas in Fayette County, Kentucky.
- 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 aminohydroxylation Target entity description: Sharpless aminohydroxylation is a stereoselective chemical reaction that converts alkenes into vicinal amino alcohols using a chiral catalyst, widely used in asymmetric synthesis.
-
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.
“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.
-
C.
New Organon
New Organon is a foundational philosophical work by Francis Bacon that proposes a new method of scientific inquiry based on empirical observation and inductive reasoning.
-
D.
CYP2J2
CYP2J2 is a human cytochrome P450 enzyme primarily expressed in the heart and other tissues, involved in the metabolism of various drugs and endogenous fatty acids.
-
E.
Lextran
Lextran is the public bus transit system serving Lexington and surrounding areas in Fayette County, Kentucky.
- F. None of above. chosen
Statements (48)
| Predicate | Object |
|---|---|
| instanceOf |
asymmetric transformation
ⓘ
chemical reaction ⓘ named reaction ⓘ oxidation reaction ⓘ |
| category |
C–N bond-forming reaction
ⓘ
C–O bond-forming reaction ⓘ stereoselective reaction ⓘ |
| developedBy | K. Barry Sharpless ⓘ |
| field |
asymmetric synthesis
ⓘ
organic chemistry ⓘ |
| givesConfiguration | predictable absolute configuration from chiral ligand ⓘ |
| hasCatalyst |
chiral catalyst
ⓘ
chiral osmium complex ⓘ |
| hasIntermediate |
osmate ester
ⓘ
osmium(VI) complex ⓘ |
| hasMechanismFeature |
nucleophilic attack on osmium intermediate
ⓘ
osmylation ⓘ syn addition ⓘ |
| hasProduct |
vicinal amino alcohol
ⓘ
β-amino alcohol ⓘ |
| hasReactant | alkene ⓘ |
| hasStereoselectivity |
enantioselective
ⓘ
stereoselective ⓘ |
| namedAfter | K. Barry Sharpless ⓘ |
| notableFeature |
broad substrate scope
ⓘ
high enantioselectivity ⓘ |
| oxidantExample |
N-methylmorpholine N-oxide
ⓘ
NMO ⓘ tert-butyl hydroperoxide ⓘ |
| reactionType | oxidative aminohydroxylation of alkenes ⓘ |
| relatedTo |
Sharpless asymmetric dihydroxylation
ⓘ
surface form:
Sharpless dihydroxylation
Sharpless epoxidation ⓘ |
| requires | oxidant to reoxidize osmium ⓘ |
| selectivityControlledBy |
chiral auxiliary on nitrogen source
ⓘ
chiral ligand ⓘ |
| substrateType |
internal alkenes
ⓘ
terminal alkenes ⓘ |
| typicalSolvent |
acetonitrile
ⓘ
polar aprotic solvent ⓘ t-butanol ⓘ |
| usedFor |
synthesis of chiral amino alcohols
ⓘ
synthesis of pharmaceutical intermediates ⓘ total synthesis of natural products ⓘ |
| usesReagent |
OsO4
ⓘ
carbamate ⓘ nitrogen source ⓘ osmium tetroxide ⓘ sulfonamide ⓘ |
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 aminohydroxylation Description of subject: Sharpless aminohydroxylation is a stereoselective chemical reaction that converts alkenes into vicinal amino alcohols using a chiral catalyst, widely used in asymmetric synthesis.
Referenced by (2)
Full triples — surface form annotated when it differs from this entity's canonical label.