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674737 Sigma-Aldrich

(R)-3,3′-Bis(triphenylsilyl)-1,1′-bi-2-naphthol

96%

Synonym: (R)-3,3′-Bis(triphenylsilyl)-1,1′-binaphthalene-2,2′-diol

  • CAS Number 111822-69-6

  • Empirical Formula (Hill Notation) C56H42O2Si2

  • Molecular Weight 803.10

  •  MDL number MFCD09265078

  •  PubChem Substance ID 24885234

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, BINOLs, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes More...
assay   96%
optical activity   [α]20/D +114°, c = 1 in chloroform
mp   103-145 °C
SMILES string   Oc1c(cc2ccccc2c1-c3c(O)c(cc4ccccc34)[Si](c5ccccc5)(c6ccccc6)c7ccccc7)[Si](c8ccccc8)(c9ccccc9)c%10ccccc%10
InChI   1S/C56H42O2Si2/c57-55-51(59(43-25-7-1-8-26-43,44-27-9-2-10-28-44)45-29-11-3-12-30-45)39-41-23-19-21-37-49(41)53(55)54-50-38-22-20-24-42(50)40-52(56(54)58)60(46-31-13-4-14-32-46,47-33-15-5-16-34-47)48-35-17-6-18-36-48/h1-40,57-58H
InChI key   STBZSRVMGWTCOU-UHFFFAOYSA-N

Description

Application

(R)-3,3′-Bis(triphenylsilyl)-1,1′-bi-2-naphthol reacts with trimethylaluminum to form a chiral organoaluminum reagent, which can catalyze the asymmetric Diels-Alder reaction of cyclopentadiene and methyl acrylate to form the corresponding Diels-Alder adduct.

Precursor to a chiral Bronsted acid (674745) used to catalyze an enantioselective aza Diels-Alder reaction providing bicyclic lactams. Rare earth metal complexes of this chiral binapthol catalyze an intramolecular hydroamination of amino olefins leading to chiral pyrrolidines.

Packaging

100 mg in clear glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

BINOL and Derivatives

BINOL and its derivatives are one of the mostly widely used classes of ligands in asymmetric synthesis; being utilized in a broad array of reactions including: Diels–Alder, carbonyl addition and redu...
William Sommer and Daniel Weibel
Aldrich ChemFiles 2008, 8.2, 56.
Keywords: Addition reactions, Alkylations, Amidations, Asymmetric synthesis, Building blocks, Catalysis, Cycloadditions, Diels-Alder reaction, Ligands, Methods, Organic synthesis, Reductions

Yamamoto Group - Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Yamamoto Group - Professor Product Portal
Keywords: Amidations, Asymmetric synthesis, Catalysis, Diels-Alder reaction, Epoxidations, Esterifications, Ligands, Oxidations

Peer-Reviewed Papers
15

References

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