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675156

Sigma-Aldrich

(R)-VANOL

97%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C32H22O2
CAS Number:
147702-13-4
Molecular Weight:
438.52
MDL number:
MFCD08459338
UNSPSC Code:
12352005
PubChem Substance ID:
24885264
NACRES:
NA.22

assay

97%

form

solid

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

Related Categories

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.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Aquatic Chronic 4 - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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(R)-(+)-1,1′-Bi(2-naphthol) 99%

Sigma-Aldrich

246948

(R)-(+)-1,1′-Bi(2-naphthol)

Blay G, et al.
Chemistry?A European Journal , 18(41), 12966-12969 (2012)
Vaulted biaryls: efficient ligands for the aluminum-catalyzed asymmetric Baeyer-Villiger reaction.
Bolm C, et al.
Synlett, 2004(09), 1619-1621 (2004)
An efficient enantioselective synthesis of florfenicol via asymmetric aziridination.
Wang Z, et al.
Tetrahedron, 67(47), 9199-9203 (2011)
Bao. J. et al.
Journal of the American Chemical Society, 118, 3392-3392 (1996)
Su Yu et al.
Organic letters, 7(3), 367-369 (2005-01-28)
[reaction: see text] In an effort to develop a synthesis of the VAPOL ligand that avoids the use of a chromium carbene complex, a route was examined that involved the annulation of a naphthalene carboxamide via the method of Snieckus.
View All Related Papers

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