674737

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

96%

• Synonym(s): (R)-3,3′-Bis(triphenylsilyl)-1,1′-binaphthalene-2,2′-diol
• Empirical Formula (Hill Notation): C₅₆H₄₂O₂Si₂
• CAS Number: 111822-69-6
• Molecular Weight: 803.10
• MDL number: MFCD09265078
• UNSPSC Code: 12352005
• PubChem Substance ID: 24885234
• NACRES: NA.22

Properties

• Quality Level: 100
• Assay: 96%
• form: solid
• 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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable