(2S)-1-[(4S)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene
[CAS# 163169-29-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (2S)-1-[(4S)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene
• Molecular Formula: C₂₈H₂₈FeNOP
• Molecular Weight: 481.35
• CAS Registry Number: 163169-29-7
• SMILES: CC(C)[C@H]1COC(=C2C=CC=C2P(c3ccccc3)c4ccccc4)[N-]1.[cH-]1cccc1.[Fe+2]

Safety Data

• Hazard Symbols: GHS07;GHS08;GHS09 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

(2S)-1-[(4S)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene is a chiral phosphino-oxazoline ligand that has gained prominence in asymmetric catalysis, particularly for its ability to induce high levels of enantioselectivity in various chemical reactions. The discovery of this compound is part of ongoing efforts to create ligands that can finely control the electronic and steric properties of metal catalysts, which are crucial for the production of chiral molecules.

The structure of this compound features a ferrocene backbone, which is known for its stability and rigidity. This backbone provides a robust framework that ensures the ligand maintains its chiral environment during catalysis. The oxazoline ring, with its chiral center, contributes to the ligand's ability to create a highly selective environment around the metal center, enhancing the enantioselectivity of the catalytic process. The isopropyl group on the oxazoline ring adds steric bulk, which further helps in controlling the outcome of the reactions.

One of the primary applications of (2S)-1-[(4S)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene is in asymmetric hydrogenation. This reaction is a cornerstone of chiral synthesis, especially in the pharmaceutical industry, where the production of enantiomerically pure compounds is often required. When coordinated with metals like rhodium or palladium, this ligand forms highly efficient catalysts that can hydrogenate a wide range of substrates, including alkenes, imines, and ketones, with excellent enantioselectivity.

Another significant application of this ligand is in asymmetric allylic substitution reactions. These reactions are vital for forming carbon-carbon and carbon-heteroatom bonds, which are essential in the synthesis of complex molecules. The chiral environment provided by this ligand ensures that these reactions proceed with high enantioselectivity, making it possible to create complex chiral molecules that serve as intermediates in the synthesis of pharmaceuticals and other fine chemicals.

In addition to these applications, (2S)-1-[(4S)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene has also been utilized in other asymmetric transformations, such as cyclopropanation and hydroformylation. These reactions benefit from the ligand's ability to create a precise chiral environment, leading to high yields of the desired enantiomer.

The development of this ligand represents a significant advancement in the field of asymmetric catalysis. Its unique structure, combining the stability of the ferrocene backbone with the chiral control provided by the oxazoline ring, has made it a valuable tool for chemists working to synthesize enantiomerically pure compounds. Its versatility and effectiveness in a wide range of reactions underscore its importance in both academic research and industrial applications.

References

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