Corey–Bakshi–Shibata reduction
E466666
The Corey–Bakshi–Shibata reduction is a widely used asymmetric organic reaction that enantioselectively reduces ketones to chiral alcohols using a chiral oxazaborolidine catalyst and borane.
All labels observed (2)
| Label | Occurrences |
|---|---|
| Corey–Bakshi–Shibata reduction canonical | 1 |
| Corey–Itsuno reduction | 1 |
How this entity was disambiguated
This entity first appeared as the object of triple T4741216 — 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–Bakshi–Shibata reduction Context triple: [E. J. Corey, developedMethod, Corey–Bakshi–Shibata reduction]
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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.
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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.
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C.
Eschenmoser–Claisen rearrangement
The Eschenmoser–Claisen rearrangement is a variant of the Claisen rearrangement in organic chemistry that converts allylic alcohols and amides into γ,δ-unsaturated carbonyl compounds via a [3,3]-sigmatropic rearrangement.
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D.
Eschenmoser
Eschenmoser is a Swiss surname most notably associated with Albert Eschenmoser, a prominent organic chemist known for his pioneering work in the synthesis of complex natural products and studies on the origin of life.
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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: Corey–Bakshi–Shibata reduction Target entity description: The Corey–Bakshi–Shibata reduction is a widely used asymmetric organic reaction that enantioselectively reduces ketones to chiral alcohols using a chiral oxazaborolidine catalyst and borane.
-
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.
Eschenmoser–Claisen rearrangement
The Eschenmoser–Claisen rearrangement is a variant of the Claisen rearrangement in organic chemistry that converts allylic alcohols and amides into γ,δ-unsaturated carbonyl compounds via a [3,3]-sigmatropic rearrangement.
-
D.
Eschenmoser
Eschenmoser is a Swiss surname most notably associated with Albert Eschenmoser, a prominent organic chemist known for his pioneering work in the synthesis of complex natural products and studies on the origin of life.
-
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 (49)
| Predicate | Object |
|---|---|
| instanceOf |
asymmetric reduction reaction
ⓘ
named reaction ⓘ organic reaction ⓘ |
| advantage |
broad substrate scope
ⓘ
catalytic amounts of chiral reagent ⓘ high enantioselectivity with simple ketones ⓘ |
| application |
preparation of enantioenriched building blocks
ⓘ
synthesis of chiral pharmaceuticals ⓘ synthesis of natural products ⓘ |
| catalystType |
Lewis acid catalyst
ⓘ
chiral oxazaborolidine ⓘ |
| commonChiralSource | amino alcohol precursors for oxazaborolidine ⓘ |
| developedBy |
Elias James Corey
ⓘ
linked to:
Elias J. Corey
H. Bakshi ⓘ R. Shibata ⓘ |
| field |
asymmetric synthesis
ⓘ
organic chemistry ⓘ |
| limitation |
borane is pyrophoric and toxic
ⓘ
sensitive to moisture ⓘ |
| mechanismFeature |
formation of a chiral oxazaborolidine–borane complex
ⓘ
hydride transfer from borane to ketone ⓘ six-membered transition state ⓘ |
| namedAfter |
Elias James Corey
ⓘ
linked to:
Elias J. Corey
H. Bakshi ⓘ R. Shibata ⓘ |
| product | chiral secondary alcohols ⓘ |
| reactionType |
asymmetric hydrogen transfer
ⓘ
enantioselective reduction ⓘ |
| relatedTo |
Corey–Itsuno reduction
ⓘ
linked to:
Corey–Bakshi–Shibata reduction
oxazaborolidine catalysts ⓘ |
| selectivity |
high chemoselectivity for ketones over other groups
ⓘ
high enantioselectivity ⓘ |
| solvent |
dichloromethane
ⓘ
toluene ⓘ |
| stereocontrol | controlled by chiral oxazaborolidine framework ⓘ |
| substrateScope |
aryl alkyl ketones
ⓘ
dialkyl ketones ⓘ heteroaryl ketones ⓘ α,β-unsaturated ketones ⓘ |
| temperature | often performed at low temperature ⓘ |
| transforms | prochiral ketones ⓘ |
| typicalCatalystLoading | 5–20 mol% ⓘ |
| typicalEnantiomericExcess |
>90% ee
ⓘ
>95% ee ⓘ |
| uses |
BH3·SMe2
ⓘ
BH3·THF ⓘ borane ⓘ chiral oxazaborolidine catalyst ⓘ |
| yearIntroduced | late 1980s ⓘ |
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: Corey–Bakshi–Shibata reduction Description of subject: The Corey–Bakshi–Shibata reduction is a widely used asymmetric organic reaction that enantioselectively reduces ketones to chiral alcohols using a chiral oxazaborolidine catalyst and borane.
Referenced by (2)
Full triples — surface form annotated when it differs from this entity's canonical label.
linked to: Corey–Bakshi–Shibata reduction