Evans aldol reaction
E635933
The Evans aldol reaction is a stereoselective carbon–carbon bond-forming reaction that uses chiral N-acyl oxazolidinone auxiliaries to control the configuration of aldol products.
Statements (50)
| Predicate | Object |
|---|---|
| instanceOf |
aldol reaction
ⓘ
carbon–carbon bond-forming reaction ⓘ organic reaction ⓘ stereoselective reaction ⓘ |
| allowsAccessTo |
anti aldol products
ⓘ
syn aldol products ⓘ |
| auxiliaryFeature |
covalently attached to substrate
ⓘ
induces high diastereoselectivity ⓘ recyclable ⓘ |
| auxiliaryRemovedBy |
hydrolysis
ⓘ
reductive cleavage ⓘ |
| controls |
relative configuration of aldol products
ⓘ
stereochemistry at the newly formed stereocenters ⓘ |
| developedInField | asymmetric induction ⓘ |
| givesProduct |
aldol adduct with defined stereochemistry
ⓘ
β-hydroxy carbonyl compound ⓘ |
| hasDiscoverer | David A. Evans NERFINISHED ⓘ |
| hasKeyIntermediate |
chiral N-acyl oxazolidinone enolate
ⓘ
metal enolate ⓘ |
| hasMechanisticStep |
C–C bond formation
ⓘ
enolate formation ⓘ protonation of aldolate ⓘ |
| hasStereocontrolOrigin |
chiral auxiliary
ⓘ
oxazolidinone ring stereocenter ⓘ |
| hasStereoselectivityType |
diastereoselective
ⓘ
enantioselective (after auxiliary removal) ⓘ |
| isCategory | named reaction in organic chemistry ⓘ |
| isRelatedTo |
Evans auxiliary
NERFINISHED
ⓘ
chiral auxiliary methodology ⓘ |
| isUsedIn |
asymmetric synthesis
ⓘ
pharmaceutical synthesis ⓘ total synthesis of natural products ⓘ |
| namedAfter | David A. Evans NERFINISHED ⓘ |
| stereochemicalOutcomeDependsOn |
enolate geometry
ⓘ
metal counterion ⓘ reaction conditions ⓘ |
| typicalAuxiliaryBackbone | oxazolidinone ⓘ |
| typicalAuxiliarySubstituent |
4-benzyl group
ⓘ
4-isopropyl group ⓘ |
| typicalElectrophile |
aldehyde
ⓘ
ketone ⓘ |
| typicalNucleophile | enolate of N-acyl oxazolidinone ⓘ |
| usesAuxiliary | Evans chiral auxiliary NERFINISHED ⓘ |
| usesAuxiliary | chiral N-acyl oxazolidinone ⓘ |
| usesBase |
LDA
ⓘ
lithium diisopropylamide ⓘ strong non-nucleophilic base ⓘ |
| usesMetalCounterion |
boron
ⓘ
titanium ⓘ |
| usesMetalCounterion | lithium ⓘ |
Referenced by (2)
Full triples — surface form annotated when it differs from this entity's canonical label.