Stork enamine reaction
E683997
The Stork enamine reaction is a key carbon–carbon bond-forming method in organic chemistry that uses enamines as nucleophiles to alkylate or acylate carbonyl compounds in a controlled, selective way.
Statements (49)
| Predicate | Object |
|---|---|
| instanceOf |
carbon–carbon bond-forming reaction
ⓘ
named reaction ⓘ organic reaction ⓘ |
| advantage |
avoids strong base required for direct enolate alkylation
ⓘ
compatible with base-sensitive functional groups ⓘ provides controlled monoalkylation ⓘ |
| bondFormed | carbon–carbon single bond ⓘ |
| category |
C–C bond formation
ⓘ
α-functionalization of carbonyl compounds ⓘ |
| developedBy | Gilbert Stork NERFINISHED ⓘ |
| field | organic chemistry ⓘ |
| hasElectrophile |
acid anhydride
ⓘ
activated carbonyl compound ⓘ acyl halide ⓘ alkyl halide ⓘ |
| hasNucleophile | enamine ⓘ |
| mechanismType | stepwise ⓘ |
| mechanisticStep |
enamine formation
ⓘ
iminium ion hydrolysis ⓘ nucleophilic acyl substitution ⓘ nucleophilic substitution ⓘ |
| namedAfter | Gilbert Stork NERFINISHED ⓘ |
| produces |
α-acylated carbonyl compound
ⓘ
α-alkylated carbonyl compound ⓘ α-substituted carbonyl compound ⓘ |
| reactionCenter | α-carbon of carbonyl compound ⓘ |
| reactivityControl | enamine nucleophilicity at α-carbon ⓘ |
| relatedTo |
Mannich reaction
NERFINISHED
ⓘ
acetoacetic ester synthesis NERFINISHED ⓘ enolate chemistry ⓘ |
| requires | formation of an enamine precursor ⓘ |
| selectivity |
often stereoselective
ⓘ
α-regioselective ⓘ |
| solvent |
aprotic solvent
ⓘ
polar solvent ⓘ |
| typicalElectrophileClass |
activated secondary alkyl halide
ⓘ
primary alkyl halide ⓘ |
| typicalEnamineSource |
aldehyde
ⓘ
ketone ⓘ secondary amine ⓘ |
| usedIn |
complex molecule synthesis
ⓘ
natural product synthesis ⓘ pharmaceutical synthesis ⓘ |
| usesReagent |
acid anhydride
ⓘ
acyl halide ⓘ alkyl halide ⓘ carbonyl compound ⓘ enamine ⓘ |
| workup | aqueous acid hydrolysis ⓘ |
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.