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406961

Sigma-Aldrich

(+)-2,2′-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline]

97%

Synonym(s):

(R,R)-2,2′-Bis(4-phenyl-2-oxazolin-2-yl)propane, (R,R)-2,2′-Isopropylidenebis(4-phenyl-2-oxazoline)

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About This Item

Empirical Formula (Hill Notation):
C21H22N2O2
CAS Number:
150529-93-4
Molecular Weight:
334.41
Beilstein/REAXYS Number:
4266906
MDL number:
MFCD00192244
UNSPSC Code:
12352005
PubChem Substance ID:
24865413
NACRES:
NA.22

assay

97%

form

solid

optical activity

[α]20/D +160°, c = 1 in ethanol

mp

56-58 °C (lit.)

storage temp.

−20°C

SMILES string

CC(C)(C1=N[C@@H](CO1)c2ccccc2)C3=N[C@@H](CO3)c4ccccc4

InChI

1S/C21H22N2O2/c1-21(2,19-22-17(13-24-19)15-9-5-3-6-10-15)20-23-18(14-25-20)16-11-7-4-8-12-16/h3-12,17-18H,13-14H2,1-2H3/t17-,18-/m0/s1

InChI key

JTNVCJCSECAMLD-ROUUACIJSA-N

Application

(+)-2,2′-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline] in the presence of copper iodide, can catalyze the asymmetric cyclopropanation reaction of phenyliodonium ylides with alkenes to form cyclopropane α-amino acid esters.
C2 symmetric ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Benoît Moreau et al.
Journal of the American Chemical Society, 127(51), 18014-18015 (2005-12-22)
A highly enantioselective (up to 97.5% ee) and diastereoselective (95:5 dr trans/cis) Cu(I)-catalyzed cyclopropanation of alkenes using phenyliodonium ylide generated in situ from iodosobenzene and methyl nitroacetate is reported. The cyclopropanation took place with high enantioselectivity for a wide range
Pfaltz, A.
Accounts of Chemical Research, 26, 339-339 (1993)
Bolm, C.
Angewandte Chemie (International Edition in English), 30, 542-542 (1991)
Gant, T.G. Meyers, A.I.
Tetrahedron, 50, 2297-2297 (1994)

Articles

C2-symmetric chiral bisoxazolines (BOX) ligands

BOX ligand complex enhances catalytic enantioselective aziridination of styrene, with phenyl substituents proving superior over t-Bu groups.

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