Trost asymmetric allylic alkylation
E408414
allylic substitution reaction
asymmetric catalysis method
carbon–carbon bond-forming reaction
chemical reaction
palladium-catalyzed reaction
Trost asymmetric allylic alkylation is a palladium-catalyzed enantioselective carbon–carbon bond-forming reaction that enables the synthesis of chiral molecules from prochiral allylic substrates.
All labels observed (1)
| Label | Occurrences |
|---|---|
| Trost asymmetric allylic alkylation canonical | 2 |
How this entity was disambiguated
This entity first appeared as the object of triple T4039213 — 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: Trost asymmetric allylic alkylation Context triple: [Barry M. Trost, knownFor, Trost asymmetric allylic alkylation]
-
A.
Sharpless asymmetric dihydroxylation
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.
-
B.
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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C.
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.
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D.
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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E.
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.
- 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: Trost asymmetric allylic alkylation Target entity description: Trost asymmetric allylic alkylation is a palladium-catalyzed enantioselective carbon–carbon bond-forming reaction that enables the synthesis of chiral molecules from prochiral allylic substrates.
-
A.
Sharpless asymmetric dihydroxylation
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.
-
B.
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.
-
C.
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.
-
D.
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.
-
E.
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.
- F. None of above. chosen
Statements (48)
| Predicate | Object |
|---|---|
| instanceOf |
allylic substitution reaction
ⓘ
asymmetric catalysis method ⓘ carbon–carbon bond-forming reaction ⓘ chemical reaction ⓘ palladium-catalyzed reaction ⓘ |
| advantage |
broad substrate scope
ⓘ
high atom economy ⓘ mild reaction conditions ⓘ |
| applicationArea |
complex molecule construction
ⓘ
medicinal chemistry ⓘ total synthesis of natural products ⓘ |
| belongsToClass | Tsuji–Trost reactions ⓘ |
| catalyst | palladium complex ⓘ |
| controls | absolute configuration of newly formed stereocenter ⓘ |
| developedBy | Barry M. Trost ⓘ |
| developedInField |
asymmetric synthesis
ⓘ
organic chemistry ⓘ |
| keyFeature |
formation of chiral centers from prochiral allylic substrates
ⓘ
high enantioselectivity ⓘ transition-metal catalysis ⓘ use of soft nucleophiles ⓘ |
| ligandRole | induces asymmetry in nucleophilic attack ⓘ |
| mechanismStep |
formation of η3-allyl–palladium complex
ⓘ
nucleophilic attack on η3-allyl–palladium complex ⓘ oxidative addition of allylic substrate to palladium(0) ⓘ reductive elimination to regenerate palladium(0) ⓘ |
| metalOxidationState | palladium(0)/palladium(II) catalytic cycle ⓘ |
| namedAfter | Barry M. Trost ⓘ |
| nucleophileType |
amine nucleophile
ⓘ
enolate nucleophile ⓘ malonate nucleophile ⓘ sulfur nucleophile ⓘ |
| reactionType |
enantioselective allylic alkylation
ⓘ
nucleophilic substitution at allylic position ⓘ |
| relatedTo |
Tsuji–Trost reactions
ⓘ
surface form:
Tsuji–Trost allylic substitution
|
| requires | chiral environment around palladium center ⓘ |
| selectivityType |
diastereoselectivity
ⓘ
enantioselectivity ⓘ regioselectivity ⓘ |
| substrateProperty | prochiral allylic substrate ⓘ |
| substrateType |
allylic acetate
ⓘ
allylic carbonate ⓘ allylic halide ⓘ |
| usedForSynthesisOf |
chiral building blocks
ⓘ
natural product fragments ⓘ pharmaceutical intermediates ⓘ |
| usesLigand |
Trost ligand
ⓘ
chiral phosphine ligand ⓘ |
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: Trost asymmetric allylic alkylation Description of subject: Trost asymmetric allylic alkylation is a palladium-catalyzed enantioselective carbon–carbon bond-forming reaction that enables the synthesis of chiral molecules from prochiral allylic substrates.
Referenced by (2)
Full triples — surface form annotated when it differs from this entity's canonical label.
subject surface form:
Barry M. Trost