Robinson annulation reaction
E545316
The Robinson annulation reaction is a classic organic chemistry transformation that forms six-membered rings by combining a Michael addition with an intramolecular aldol condensation, widely used in the synthesis of complex cyclic molecules and natural products.
Observed surface forms (1)
| Surface form | Occurrences |
|---|---|
| Robinson–Schöpf reaction | 1 |
Statements (47)
| Predicate | Object |
|---|---|
| instanceOf |
annulation reaction
ⓘ
carbon–carbon bond-forming reaction ⓘ name reaction ⓘ organic reaction ⓘ |
| appearsIn | organic chemistry textbooks ⓘ |
| category |
carbonyl chemistry
ⓘ
pericyclic-related transformations ⓘ |
| combines |
Michael addition
ⓘ
intramolecular aldol condensation ⓘ |
| developedIn | 20th century ⓘ |
| forms | C–C bonds ⓘ |
| importantFor | asymmetric synthesis ⓘ |
| mechanisticStep |
1,4-conjugate addition
ⓘ
dehydration ⓘ enolate formation ⓘ intramolecular aldol addition ⓘ |
| namedAfter | Robert Robinson NERFINISHED ⓘ |
| productFeature |
conjugated enone system
ⓘ
ring formation ⓘ |
| reactionType | conjugate addition–condensation sequence ⓘ |
| relatedTo |
Dieckmann condensation
NERFINISHED
ⓘ
Michael reaction ⓘ aldol reaction ⓘ |
| requires | base ⓘ |
| ringSize | six-membered ring ⓘ |
| stereochemicalOutcome | creates stereocenters ⓘ |
| taughtIn | advanced organic chemistry courses ⓘ |
| typicalBase |
alkoxide base
ⓘ
hydroxide base ⓘ |
| typicalElectrophile |
enone
ⓘ
α,β-unsaturated carbonyl compound ⓘ |
| typicalNucleophile |
enolate
ⓘ
ketone enolate ⓘ |
| typicalProduct |
cyclohexenone
ⓘ
six-membered carbocycle ⓘ |
| typicalSolvent |
alcohol solvent
ⓘ
ethanol ⓘ |
| typicalSubstrate |
1,3-dicarbonyl compound
ⓘ
cyclic ketone ⓘ methyl vinyl ketone ⓘ |
| usedFor |
construction of bicyclic systems
ⓘ
construction of polycyclic frameworks ⓘ construction of tricyclic systems ⓘ |
| usedIn |
natural product synthesis
ⓘ
steroid synthesis ⓘ synthesis of complex cyclic molecules ⓘ total synthesis ⓘ |
Referenced by (2)
Full triples — surface form annotated when it differs from this entity's canonical label.
this entity surface form:
Robinson–Schöpf reaction