Corey–Winter olefin synthesis
E466668
Corey–Winter olefin synthesis is an organic reaction that converts 1,2-diols into alkenes via cyclic thiocarbonate intermediates, widely used for stereospecific formation of double bonds.
Statements (47)
| Predicate | Object |
|---|---|
| instanceOf |
named reaction
ⓘ
olefination reaction ⓘ organic reaction ⓘ |
| advantage |
avoids strong acidic conditions
ⓘ
preserves stereochemistry of starting diol ⓘ |
| application |
construction of defined alkene geometry
ⓘ
stereospecific formation of double bonds ⓘ synthesis of complex natural products ⓘ |
| bondChange |
C=C bond formation
ⓘ
C–O bond cleavage ⓘ |
| classification | two-step transformation via isolable intermediate ⓘ |
| commonUseCase |
conversion of acyclic 1,2-diols to acyclic alkenes
ⓘ
conversion of cyclic 1,2-diols to cycloalkenes ⓘ |
| converts | 1,2-diols ⓘ |
| developedBy |
E. J. Corey
NERFINISHED
ⓘ
S. Winter NERFINISHED ⓘ |
| field | organic chemistry ⓘ |
| intermediateType | cyclic thiocarbonate ester ⓘ |
| keyIntermediate | cyclic thiocarbonate ⓘ |
| limitation |
best suited to 5-membered cyclic thiocarbonates
ⓘ
requires formation of cyclic thiocarbonate ⓘ |
| mechanismFeature |
elimination of carbonyl sulfide or related species
ⓘ
phosphite-induced fragmentation ⓘ |
| mechanisticStep |
formation of cyclic thiocarbonate from 1,2-diol
ⓘ
fragmentation of cyclic thiocarbonate to alkene ⓘ |
| naming | named after E. J. Corey and S. Winter ⓘ |
| produces | alkenes ⓘ |
| productGeometryControl | alkene geometry dictated by diol configuration ⓘ |
| reactionCondition | often performed under mild conditions ⓘ |
| reactionType | deoxygenation ⓘ |
| relatedTo |
dehydration of diols
ⓘ
olefination reactions ⓘ |
| selectivity | high stereoselectivity for E or Z alkene depending on diol geometry ⓘ |
| stereochemicalOutcome |
retention of relative configuration of the diol
ⓘ
stereospecific ⓘ |
| substrateRequirement |
neighboring hydroxyl groups
ⓘ
vicinal diol configuration ⓘ |
| typicalProduct | disubstituted alkene ⓘ |
| typicalStartingMaterial |
1,2-diol
ⓘ
vicinal diol ⓘ |
| usedIn |
laboratory organic synthesis
ⓘ
stereocontrolled synthesis of alkenes ⓘ |
| usesReagent |
phosgene equivalents
ⓘ
thiocarbonyldiimidazole ⓘ thiophosgene ⓘ trialkyl phosphite ⓘ trimethyl phosphite ⓘ |
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.