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246956 Aldrich

(S)-(−)-1,1′-Bi(2-naphthol)

99%

Synonym: (−)-2,2′-Dihydroxy-1,1′-dinaphthyl, (S)-(−)-1,1′-Binaphthalene-2,2′-diol, (S)-BINOL

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Properties

Related Categories Asymmetric Synthesis, BINOLs, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes More...
InChI Key   PPTXVXKCQZKFBN-UHFFFAOYSA-N
assay   99%
optical activity   [α]22/D −34°, c = 1 in THF
optical purity   ee: 99% (HPLC)
mp   208-210 °C(lit.)

Description

Packaging

1, 5, 25 g in glass bottle

Application

(S)-BINOL ligand in combination with titanium(IV) isopropoxide, forms (S)-(-)-BINOL-Ti complex, which is an effective chiral catalyst for:
• asymmetric addition of alkynylzinc to unactivated ketones
• enantioselective ring-opening reaction of meso-stilbene oxide and cyclohexene oxide with anilines
• asymmetric aryl transfers from triaryl(tetrahydrofuran)aluminum reagents to a wide variety of ketones
It can also react with zirconium(IV) isopropoxide isopropanol complex to form a chiral Lewis acid catalyst for the facile enantioselective allylation of aldehydes by allyltributyltin.

Precursor to phosphoramidite catalyst employed in a conversion of allylic alcohols to allylic amines.

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Laboratory Gloves
Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
DU3106100
Protocols & Articles

Articles

Indanols

These chiral imine-ligands have recently been used in the vanadium-catalyzed oxidation of sulfides in conjunction with hydrogen peroxide. Optically active sulfoxides are obtained in high yields and e...
Aldrich ChemFiles 2005, 5.4, 7.
Keywords: Asymmetric synthesis, Catalysis, Chemfiles, Ligands, Oxidations

Peer-Reviewed Papers
15

References

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