Structure via PubChem · Public domain (PubChem)
L-selectride
Sign in to saveAlso known as lithium tri-sec-butylborohydride
L-selectride is a organoboron compound with the chemical formula . A colorless salt, it is usually dispensed as a solution in THF. As a particularly basic and bulky borohydride, it is used for stereoselective reduction of ketones to alcohols. == Use in synthesis == Like other borohydrides, reductions are effected in two steps: delivery of the hydride equivalent to give the lithium alkoxide followed by hydrolytic workup:
Chemical data
- Formula
- C12H28BLi
- Molecular weight
- 190.1 g/mol
- IUPAC name
- lithium tri(butan-2-yl)boranuide
- SMILES
- [Li+].[BH-](C(C)CC)(C(C)CC)C(C)CC
- InChIKey
- ACJKNTZKEFMEAK-UHFFFAOYSA-N
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Has part
- boron
- Mass
- 190.244
Show 3 more facts
- chemical formula
- C₁₂H₂₈BLi
- Commons category
- L-selectride
- canonical SMILES
- [Li+].[BH-](C(C)CC)(C(C)CC)C(C)CC
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Use in synthesis
- Related compounds
- Related compounds
- References
L-selectride is a organoboron compound with the chemical formula . A colorless salt, it is usually dispensed as a solution in THF. As a particularly basic and bulky borohydride, it is used for stereoselective reduction of ketones to alcohols. == Use in synthesis == Like other borohydrides, reductions are effected in two steps: delivery of the hydride equivalent to give the lithium alkoxide followed by hydrolytic workup:
The selectivity of this reagent is illustrated by its reduction of all three methylcyclohexanones to the less stable methylcyclohexanols in >98% yield.
Excerpted from Wikipedia’s “L-selectride” article, available under the CC BY-SA 4.0 licence.