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417068 Sigma-Aldrich

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

97%

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

  • CAS Number 150639-33-1

  • Empirical Formula (Hill Notation) C20H17N3O2

  • Molecular Weight 331.37

  •  MDL number MFCD00192394

  •  PubChem Substance ID 24866118

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, BOX, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Privileged Ligands and Complexes More...
assay   97%
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

Description

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.

Packaging

1 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

BOX

C2-symmetric chiral bisoxazolines (BOX) are privileged structures because they promote a great number of transformations with unprecedented selectivity.1 In 1991, in the same Journal of American Chem...
William Sommer and Daniel Weibel
ChemFiles 2008, 8.2, 64.
Keywords: Addition reactions, Asymmetric synthesis, Catalysis, Cyclopropanations, Ligands, transformation

Peer-Reviewed Papers
15

References

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