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417068

Sigma-Aldrich

(4S)-(+)-Phenyl-α-[(4S)-phenyloxazolidin-2-ylidene]-2-oxazoline-2-acetonitrile

97%

Synonym(s):

(S,S)-4-Phenyl-α-(4-phenyloxazolidin-2-ylidene)-2-oxazoline-2-acetonitrile

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About This Item

Empirical Formula (Hill Notation):
C20H17N3O2
CAS Number:
150639-33-1
Molecular Weight:
331.37
MDL number:
MFCD00192394
UNSPSC Code:
12352005
PubChem Substance ID:
24866118
NACRES:
NA.22

assay

97%

form

solid

optical activity

[α]20/D +364°, c = 1 in chloroform

mp

146-148 °C (lit.)

SMILES string

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

InChI

1S/C20H17N3O2/c21-11-16(19-22-17(12-24-19)14-7-3-1-4-8-14)20-23-18(13-25-20)15-9-5-2-6-10-15/h1-10,17-18,22H,12-13H2/b19-16-/t17-,18-/m1/s1

InChI key

QVVGSAYHUSBCQV-SRKGJJLTSA-N

General description

(4S)-(+)-Phenyl-α-[(4S)-phenyloxazolidin-2-ylidene]-2-oxazoline-2-acetonitrile is a C2-symmetric chiral bisoxazoline (BOX) ligand.

Application

(4S)-(+)-Phenyl-α-[(4S)-phenyloxazolidin-2-ylidene]-2-oxazoline-2-acetonitrile/Re(V)-oxo complex can catalyze the asymmetric hydrosilylation of ketones.
Ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.

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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Enantioselective Reduction of Ketones and Imines Catalyzed by (CN-Box) ReV-Oxo Complexes.
Nolin KA, et al.
Chemistry?A European Journal , 16(31), 9555-9562 (2010)
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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