Shi epoxidation
E1032134
Shi epoxidation is an asymmetric organocatalytic reaction that converts alkenes to chiral epoxides using a fructose-derived ketone catalyst and an oxidant such as oxone.
Statements (47)
| Predicate | Object |
|---|---|
| instanceOf |
asymmetric epoxidation
ⓘ
organic reaction ⓘ organocatalytic reaction ⓘ oxidation reaction ⓘ |
| advantage |
high enantioselectivity
ⓘ
metal-free catalysis ⓘ use of inexpensive oxidant ⓘ |
| appliesTo |
conjugated alkenes
ⓘ
electron-rich alkenes ⓘ styrene derivatives ⓘ |
| catalystClass | chiral dioxirane precursor ⓘ |
| catalystOrigin |
carbohydrate-derived ketone
ⓘ
fructose-derived chiral scaffold ⓘ |
| catalystRole | induces chirality in epoxide product ⓘ |
| comparedTo |
Jacobsen–Katsuki epoxidation
NERFINISHED
ⓘ
Sharpless epoxidation NERFINISHED ⓘ |
| developedBy | Yian Shi NERFINISHED ⓘ |
| field |
asymmetric synthesis
ⓘ
organocatalysis ⓘ |
| goal | synthesis of optically active epoxides ⓘ |
| hasSubstrate | alkenes ⓘ |
| mechanismFeature |
dioxirane intermediate
ⓘ
in situ generated dioxirane oxidant ⓘ |
| namedAfter | Yian Shi NERFINISHED ⓘ |
| notableFeature | organocatalytic alternative to metal-based epoxidations ⓘ |
| oxidantClass | peroxymonosulfate-based oxidant ⓘ |
| oxidantRole | generates dioxirane from ketone catalyst ⓘ |
| produces | chiral epoxides ⓘ |
| productType | epoxides with defined absolute configuration ⓘ |
| reactionCondition |
aqueous conditions
ⓘ
mild temperatures ⓘ |
| reactionMedium |
aqueous organic solvent mixture
ⓘ
biphasic system ⓘ |
| reactionStep |
oxidation of chiral ketone to dioxirane
ⓘ
oxygen transfer from dioxirane to alkene ⓘ |
| reactionType | enantioselective epoxidation ⓘ |
| selectivityType |
diastereoselective
ⓘ
enantioselective ⓘ |
| stereocontrolSource | chiral ketone catalyst ⓘ |
| usedIn |
pharmaceutical synthesis
ⓘ
total synthesis of natural products ⓘ |
| usesAdditive |
buffer
ⓘ
phase-transfer agent ⓘ |
| usesCatalyst |
chiral ketone catalyst
ⓘ
fructose-derived ketone ⓘ |
| usesOxidant |
oxone
ⓘ
potassium peroxymonosulfate ⓘ |
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.