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 |
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 ⓘ |
Referenced by (2)
Full triples — surface form annotated when it differs from this entity's canonical label.
subject surface form:
Barry M. Trost