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675156 Sigma-Aldrich

(R)-VANOL

97%

Synonym: (R)-3,3′-Diphenyl-2,2′-bi-1-naphthalol, (R)-3,3′-Diphenyl-2,2′-bi-1-naphthol

  • CAS Number 147702-13-4

  • Empirical Formula (Hill Notation) C32H22O2

  • Molecular Weight 438.52

  •  MDL number MFCD08459338

  •  PubChem Substance ID 24885264

  •  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   97%
optical activity   [α]20/D +310°, c = 1 in chloroform
mp   200-204 °C
SMILES string   Oc1c(c(cc2ccccc12)-c3ccccc3)-c4c(O)c5ccccc5cc4-c6ccccc6
InChI   1S/C32H22O2/c33-31-25-17-9-7-15-23(25)19-27(21-11-3-1-4-12-21)29(31)30-28(22-13-5-2-6-14-22)20-24-16-8-10-18-26(24)32(30)34/h1-20,33-34H
InChI key   NDTDVKKGYBULHF-UHFFFAOYSA-N

Description

Application

(R)-VANOL is a vaulted biaryl ligand that may be used in the following processes:
• Transformation of 3-substituted cyclobutanones to enantiopure γ-butyrolactones via asymmetric Baeyer-Villiger Reaction in the presence of an aluminum catalyst.
• Asymmetric aziridination of N-(4-(Methylsulfonyl)benzylidene)diphenylmethanamine to form (2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl) aziridine-2-carboxylate.
• Conjugate addition of terminal alkynes to 2-arylidene-1,3-diketones with high enantioselectivity in the presence of diethyl zinc.

VANOL has proven to be an excellent ligand in catalytic asymmetric Diels-Alder, imine aldol, and aziridination reactions.

Packaging

250 mg in amber glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles

Articles

Vaulted Biaryl Ligands and BINOL Derivatives

BINOL and its derivatives are some of the mostly widely used classes of ligands in asymmetric synthesis, and are utilized in a broad array of reaction classes including: Diels-Alder, ene, carbonyl ad...
Aldrich ChemFiles 2006, 6.10, 5.
Keywords: Addition reactions, Alkylations, Amidations, Aminations, Asymmetric synthesis, Building blocks, Catalysis, Chemfiles, Cycloadditions, Ligands, Methods, Organic synthesis, Protocols, Reductions, Reductive aminations, Substitutions

Wulff Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Wulff Group – Professor Product Portal
Keywords: Annulations, Asymmetric catalysis, Asymmetric synthesis, Aziridinations, Benzannulations, Catalysis, Ligands, Organic synthesis, Research areas

Peer-Reviewed Papers
15

References

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