Corey–Chaykovsky reagent
E466670
The Corey–Chaykovsky reagent is an organosulfur ylide reagent widely used in organic synthesis to convert carbonyl compounds into epoxides and aziridines.
Observed surface forms (1)
| Surface form | Occurrences |
|---|---|
| Liotta reagent | 1 |
Statements (48)
| Predicate | Object |
|---|---|
| instanceOf |
named reaction reagent
ⓘ
organosulfur compound ⓘ synthetic reagent ⓘ ylide reagent ⓘ |
| advantages |
high stereocontrol
ⓘ
mild reaction conditions ⓘ operational simplicity ⓘ |
| baseUsedWith |
potassium tert-butoxide
ⓘ
sodium hydride ⓘ |
| category |
aziridination reagents
ⓘ
epoxidation reagents ⓘ organosulfur ylides ⓘ |
| developedBy |
Elias James Corey
NERFINISHED
ⓘ
Michael Chaykovsky NERFINISHED ⓘ |
| discoveredIn | 1960s ⓘ |
| field | organic chemistry ⓘ |
| hasComponent |
sulfonium ylide
ⓘ
sulfoxonium ylide ⓘ |
| mechanismFeature |
betainic intermediate formation
ⓘ
intramolecular SN2 ring closure ⓘ |
| namedAfter |
Elias James Corey
NERFINISHED
ⓘ
Michael Chaykovsky NERFINISHED ⓘ |
| produces |
aziridines
ⓘ
epoxides ⓘ |
| reactionType |
1,2-addition to C=O bond
ⓘ
nucleophilic addition to carbonyl group ⓘ ring-forming reaction ⓘ |
| relatedReaction |
Corey–Chaykovsky aziridination
NERFINISHED
ⓘ
Corey–Chaykovsky epoxidation NERFINISHED ⓘ |
| relatedTo |
Wittig reagent
ⓘ
sulfonium ylides ⓘ sulfoxonium ylides ⓘ |
| selectivity |
chemoselective for carbonyl groups
ⓘ
tolerant of many functional groups ⓘ |
| solvent |
dimethyl sulfoxide
ⓘ
polar aprotic solvents ⓘ |
| stereochemicalOutcome |
retention of configuration at carbonyl carbon
ⓘ
stereospecific epoxide formation ⓘ |
| typicalForm |
dimethyloxosulfonium methylide
ⓘ
trimethylsulfonium iodide-derived ylide ⓘ |
| usedFor |
aziridination of imines
ⓘ
conversion of aldehydes to epoxides ⓘ conversion of imines to aziridines ⓘ conversion of ketones to epoxides ⓘ epoxidation of carbonyl compounds ⓘ |
| usedIn |
medicinal chemistry
ⓘ
natural product synthesis ⓘ stereoselective synthesis ⓘ |
Referenced by (2)
Full triples — surface form annotated when it differs from this entity's canonical label.