(2R)-1-[(4S)-4,5-Dihydro-4-phenyl-2-oxazolyl]-2-(diphenylphosphino)ferrocene
[CAS# 163169-12-8]

Identification

• Classification: Organic raw materials >> Organometallic compound >> Organic ruthenium
• Name: (2R)-1-[(4S)-4,5-Dihydro-4-phenyl-2-oxazolyl]-2-(diphenylphosphino)ferrocene
• Molecular Formula: C₃₁H₂₆FeNOP
• Molecular Weight: 515.36
• CAS Registry Number: 163169-12-8
• SMILES: C1C(N=C(O1)[C]2[CH][CH][CH][C]2P(C3=CC=CC=C3)C4=CC=CC=C4)C5=CC=CC=C5.[CH]1[CH][CH][CH][CH]1.[Fe]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

(2R)-1-[(4S)-4,5-Dihydro-4-phenyl-2-oxazolyl]-2-(diphenylphosphino)ferrocene, a chiral phosphino-oxazoline ligand, plays a significant role in asymmetric catalysis. Its unique structure, combining a ferrocene backbone with a phosphine and oxazoline ring, allows for precise control over the electronic and steric properties of metal catalysts, making it a valuable tool in the synthesis of chiral molecules.

The discovery of this compound is rooted in the broader quest to develop ligands capable of inducing high enantioselectivity in catalytic reactions. The incorporation of the ferrocene unit offers stability and rigidity, which is essential for maintaining the chiral environment around the metal center. The oxazoline ring contributes to the fine-tuning of the steric environment, further enhancing the ligand's ability to induce high levels of enantioselectivity.

One of the key applications of this ligand is in asymmetric hydrogenation, where it has demonstrated exceptional performance in producing chiral products from prochiral substrates. When coordinated with metals such as rhodium or palladium, the resulting catalyst efficiently hydrogenates alkenes, imines, and ketones, leading to high yields of the desired enantiomer. This capability is particularly important in the pharmaceutical industry, where the production of enantiomerically pure drugs is often required to meet regulatory standards and therapeutic efficacy.

Another important application is in asymmetric allylic substitution reactions, which are essential for forming carbon-carbon and carbon-heteroatom bonds. The chiral environment provided by this ligand ensures high enantioselectivity in these reactions, making it possible to synthesize complex chiral molecules that are valuable intermediates in drug synthesis and other fine chemicals.

Moreover, this ligand has also found use in a variety of other asymmetric transformations, such as cyclopropanation and hydroformylation, where its ability to create a highly selective chiral environment around the metal center is crucial for the success of the reaction. The versatility and efficiency of this ligand in promoting asymmetric reactions have made it a staple in both academic research and industrial applications.

In terms of its structure, the ferrocene backbone provides a stable and rigid framework, while the oxazoline ring offers additional steric control, which is essential for achieving high enantioselectivity. The combination of these features makes (2R)-1-[(4S)-4,5-Dihydro-4-phenyl-2-oxazolyl]-2-(diphenylphosphino)ferrocene a powerful ligand for asymmetric catalysis.