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688495 Sigma-Aldrich

(S)-4-tert-Butyl-2-[2-(diphenylphosphino)phenyl]-2-oxazoline

97%

Synonym: (4S)-tert-Butyl-2-[2-(diphenylphosphino)phenyl]-4,5-dihydrooxazole

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, PHOX, Privileged Ligands and Complexes More...
Quality Level   100
assay   97%
optical activity   [α]22/D -57.0°, c = 1 in chloroform
mp   111-116 °C
storage temp.   −20°C
SMILES string   CC(C)(C)[C@@H]1N=C(C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4)OC1
InChI   1S/C25H26NOP/c1-25(2,3)23-18-27-24(26-23)21-16-10-11-17-22(21)28(19-12-6-4-7-13-19)20-14-8-5-9-15-20/h4-17,23H,18H2,1-3H3/t23-/m1/s1
InChI key   DMOLTNKQLUAXPI-HSZRJFAPSA-N

Description

General description

The product is a phosphinooxazoline (PHOX) ligand introduced by Pfaltz and coworkers. These non-symmetrical modular P,N-ligands are particularly useful in cases where double bond migration leads to undesired products or mixtures of isomers.

Application

(S)-4-tert-Butyl-2-[2-(diphenylphosphino)phenyl]-2-oxazoline can be used as a ligand for enantioselective Heck reaction without any C=C double bond migration byproduct. It can also be used in a rhodium(I)-catalyzed enantioselective desymmetrization reaction of meso-3,5-dimethyl glutaric anhydride, to form substituted syn-deoxypolypropionate fragments in a single transformation.

Packaging

100 mg in clear glass bottle

500 mg in amber 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

PHOX

Of the thousands of chiral ligands used in asymmetric synthesis a relatively large number exhibit C2-symmetry. More recently, non-symmetrical modular P,N-ligands have been introduced independently by...
William Sommer and Daniel Weibel
Chemfiles Volume 8 Article 2
Keywords: Alkylations, Asymmetric synthesis, Catalysis, Desymmetrizations, Heck Reaction, Hydrogenations, Ligands, Pauson-Khand Reaction, Reductions, transformation

Pfaltz Group - Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Pfaltz Group - Professor Product Portal
Keywords: Asymmetric catalysis, Asymmetric synthesis, Catalysis, Hydrogenations, Ligands

Peer-Reviewed Papers
15

References

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