Stork–Danheiser rearrangement
E683998
The Stork–Danheiser rearrangement is an organic reaction that transforms certain allylic alcohol derivatives into rearranged carbonyl compounds via a sigmatropic shift, widely used in complex molecule synthesis.
Statements (43)
| Predicate | Object |
|---|---|
| instanceOf |
named reaction
ⓘ
organic reaction ⓘ rearrangement reaction ⓘ |
| application |
construction of quaternary carbon centers
ⓘ
synthesis of polycyclic frameworks ⓘ |
| bondChange |
C–C bond migration
ⓘ
formation of carbonyl group ⓘ |
| category |
carbon–carbon bond-forming reaction
ⓘ
pericyclic reaction ⓘ |
| drivingForce | formation of conjugated carbonyl system ⓘ |
| field | organic chemistry ⓘ |
| governedBy | orbital symmetry rules ⓘ |
| importance |
enables strategic skeletal reorganization
ⓘ
valuable for late-stage functionalization ⓘ |
| involvesIntermediate |
allylic cation-like transition state
ⓘ
enone intermediate ⓘ |
| keyStep | [3,3]-sigmatropic rearrangement ⓘ |
| levelOfUse | widely used in complex synthesis ⓘ |
| mechanismFeature | sigmatropic shift ⓘ |
| namedAfter |
Gilbert Stork
NERFINISHED
ⓘ
Robert L. Danheiser NERFINISHED ⓘ |
| operatesThrough | concerted pericyclic transition state ⓘ |
| productClass |
aldehydes
ⓘ
ketones ⓘ |
| productType | rearranged carbonyl compounds ⓘ |
| reactionClass | allylic to carbonyl rearrangement ⓘ |
| reactionType |
allylic rearrangement
ⓘ
sigmatropic rearrangement ⓘ |
| relatedTo |
Claisen rearrangement
NERFINISHED
ⓘ
Eschenmoser–Claisen rearrangement NERFINISHED ⓘ Ireland–Claisen rearrangement NERFINISHED ⓘ |
| selectivity |
regioselective
ⓘ
stereoselective ⓘ |
| substrateClass | allylic alcohols ⓘ |
| substrateClass | allylic esters ⓘ |
| substrateClass | allylic ethers ⓘ |
| transforms | allylic alcohol derivatives ⓘ |
| typicalContext | multistep synthetic sequences ⓘ |
| typicalOutcome | migration of substituent along allylic system ⓘ |
| usedBy | synthetic organic chemists ⓘ |
| usedIn |
complex molecule synthesis
ⓘ
natural product synthesis ⓘ total synthesis ⓘ |
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.