Corey–Bakshi–Shibata reduction
E466666
The Corey–Bakshi–Shibata reduction is a widely used asymmetric organic reaction that enantioselectively reduces ketones to chiral alcohols using a chiral oxazaborolidine catalyst and borane.
Statements (49)
| Predicate | Object |
|---|---|
| instanceOf |
asymmetric reduction reaction
ⓘ
named reaction ⓘ organic reaction ⓘ |
| advantage |
broad substrate scope
ⓘ
catalytic amounts of chiral reagent ⓘ high enantioselectivity with simple ketones ⓘ |
| application |
preparation of enantioenriched building blocks
ⓘ
synthesis of chiral pharmaceuticals ⓘ synthesis of natural products ⓘ |
| catalystType |
Lewis acid catalyst
ⓘ
chiral oxazaborolidine ⓘ |
| commonChiralSource | amino alcohol precursors for oxazaborolidine ⓘ |
| developedBy |
Elias James Corey
NERFINISHED
ⓘ
H. Bakshi NERFINISHED ⓘ R. Shibata NERFINISHED ⓘ |
| field |
asymmetric synthesis
ⓘ
organic chemistry ⓘ |
| limitation |
borane is pyrophoric and toxic
ⓘ
sensitive to moisture ⓘ |
| mechanismFeature |
formation of a chiral oxazaborolidine–borane complex
ⓘ
hydride transfer from borane to ketone ⓘ six-membered transition state ⓘ |
| namedAfter |
Elias James Corey
NERFINISHED
ⓘ
H. Bakshi NERFINISHED ⓘ R. Shibata NERFINISHED ⓘ |
| product | chiral secondary alcohols ⓘ |
| reactionType |
asymmetric hydrogen transfer
ⓘ
enantioselective reduction ⓘ |
| relatedTo |
Corey–Itsuno reduction
NERFINISHED
ⓘ
oxazaborolidine catalysts ⓘ |
| selectivity |
high chemoselectivity for ketones over other groups
ⓘ
high enantioselectivity ⓘ |
| solvent |
dichloromethane
ⓘ
toluene ⓘ |
| stereocontrol | controlled by chiral oxazaborolidine framework ⓘ |
| substrateScope |
aryl alkyl ketones
ⓘ
dialkyl ketones ⓘ heteroaryl ketones ⓘ α,β-unsaturated ketones ⓘ |
| temperature | often performed at low temperature ⓘ |
| transforms | prochiral ketones ⓘ |
| typicalCatalystLoading | 5–20 mol% ⓘ |
| typicalEnantiomericExcess |
>90% ee
ⓘ
>95% ee ⓘ |
| uses |
BH3·SMe2
ⓘ
BH3·THF ⓘ borane ⓘ chiral oxazaborolidine catalyst ⓘ |
| yearIntroduced | late 1980s ⓘ |
Referenced by (1)
Full triples — surface form annotated when it differs from this entity's canonical label.