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

Name: (<I>R</I>)-3,3′-Bis(triphenylsilyl)-1,1′-bi-2-naphthol
Brand: ALDRICH
Price: 216 USD
Availability: InStock

96%

Synonym(s):

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

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About This Item

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

Key Documents

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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

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Catalysts

Chiral Catalysts & Ligands

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1 of 4

This Item	681539	690007	246948
Sigma-Aldrich 674737 (R)-3,3′-Bis(triphenylsilyl)-1,1′-bi-2-naphthol	Sigma-Aldrich 681539 (S)-(–)-3-3′-Bis(3,5-bis(trifluoromethyl)phenyl)-1,1′-bi-2-naphthol	Sigma-Aldrich 690007 (S)-3,3′-Bis(2,4,6-triisopropylphenyl)-1,1′-bi-2-naphthol	Sigma-Aldrich 246948 (R)-(+)-1,1′-Bi(2-naphthol)
assay 96%	assay 95%	assay 95% (HPLC)	assay 99%
form solid	form (Powder or Crystals or Solid or Chunks)	form solid	form solid
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
mp 103-145 °C	mp 215-219 °C	mp -	mp 208-210 °C (lit.)
optical activity [α]20/D +114°, c = 1 in chloroform	optical activity [α]22/D -56°, c = 1 in chloroform	optical activity -	optical activity [α]21/D +34°, c = 1 in THF

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.[1]

Precursor to a chiral Bronsted acid (674745) used to catalyze an enantioselective aza Diels-Alder reaction providing bicyclic lactams.[2] Rare earth metal complexes of this chiral binapthol catalyze an intramolecular hydroamination of amino olefins leading to chiral pyrrolidines.[3]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Asymmetric Diels-Alder Reaction of Cyclopentadiene and Methyl Acrylate Catalyzed by Chiral Organoaluminum Reagents.

Bulletin of the Chemical Society of Japan, 65(12), 3501-3503 (1992)

Enantioselective direct aza hetero-Diels-Alder reaction catalyzed by chiral Brønsted acids.

Hua Liu et al.

Organic letters, 8(26), 6023-6026 (2006-12-15)

[Structure: see text] The first chiral Brønsted acid-catalyzed asymmetric direct aza hetero-Diels-Alder reaction has been described. The phosphoric acids, prepared from binol and H8-binol derivatives, have shown catalytic ability for the reaction of cyclohexenone with N-PMP-benzaldimine. A chiral phosphoric acid

3,3'-Bis(trisarylsilyl)-substituted binaphtholate rare earth metal catalysts for asymmetric hydroamination.

Denis V Gribkov et al.

Journal of the American Chemical Society, 128(11), 3748-3759 (2006-03-16)

Chiral 3,3'-bis(trisarylsilyl)-substituted binaphtholate rare earth metal complexes (R)-[Ln{Binol-SiAr3}(o-C6H4CH2NMe2)(Me2NCH2Ph)] (Ln = Sc, Lu, Y; Binol-SiAr3 = 3,3'-bis(trisarylsilyl)-2,2'-dihydroxy-1,1'-binaphthyl; Ar = Ph (2-Ln), 3,5-xylyl (3-Ln)) and (R)-[La{Binol-Si(3,5-xylyl)3}{E(SiMe3)2}(THF)2] (E = CH (4a), N (4b)) are accessible via facile arene, alkane, and amine elimination. They

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