(2R)-1-[(4S)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene
[CAS# 163169-10-6]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (2R)-1-[(4S)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene
• Molecular Formula: C₂₈H₂₈FeNOP
• Molecular Weight: 481.35
• CAS Registry Number: 163169-10-6
• SMILES: CC(C)[C@H]1COC(C23=C4C5=C6C2(P(C7=CC=CC=C7)C8=CC=CC=C8)[Fe+2]6549%10%11%123C%13C9=C%10C%11=C%13%12)=N1

Safety Data

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

Discovery and Applications

(2R)-1-[(4S)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene, also known as a chiral ferrocenyl phosphine-oxazoline ligand, is an important compound in asymmetric catalysis. This molecule has gained considerable interest due to its ability to facilitate highly enantioselective reactions, making it a valuable tool in the synthesis of chiral molecules, especially in the pharmaceutical industry.

The discovery of this compound is part of the broader effort to develop chiral ligands that can induce high levels of enantioselectivity in various catalytic processes. The unique structure of this compound, which combines a ferrocene backbone with a phosphine group and an oxazoline ring, allows it to finely control both the electronic and steric environment around a metal center in a catalyst. This control is crucial for achieving high selectivity in asymmetric reactions, where the goal is to produce one enantiomer of a product preferentially over the other.

In terms of application, (2R)-1-[(4S)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene has proven to be particularly effective in asymmetric hydrogenation reactions. When coordinated with transition metals such as palladium or rhodium, this ligand forms highly active catalysts that can reduce prochiral substrates, such as alkenes, imines, and ketones, to their corresponding chiral products with excellent enantioselectivity. This capability is of great significance in the pharmaceutical industry, where the synthesis of enantiomerically pure drugs is often required to meet regulatory standards and ensure therapeutic efficacy.

Another key application of this chiral ligand is in asymmetric allylic substitution reactions. These reactions are valuable for creating carbon-carbon and carbon-heteroatom bonds in a stereoselective manner, allowing access to a wide range of chiral molecules that are important intermediates in the synthesis of complex natural products and active pharmaceutical ingredients. The ligand’s chiral environment ensures that these reactions proceed with high selectivity, producing the desired enantiomer in high yield.

In addition to these applications, the ligand has also been used in various other asymmetric catalytic processes, including cyclopropanation, hydroformylation, and cross-coupling reactions. The versatility of (2R)-1-[(4S)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene in promoting these reactions has made it a valuable tool for researchers and industry professionals seeking to synthesize chiral compounds efficiently.

One of the most notable aspects of this ligand is its ability to form stable complexes with transition metals, which are crucial for catalytic activity. The presence of the ferrocene backbone in the ligand structure not only imparts stability but also allows for fine-tuning of the electronic properties of the metal center, enhancing the reactivity and selectivity of the catalyst. The oxazoline ring, meanwhile, provides additional steric control, further contributing to the high enantioselectivity observed in reactions involving this ligand.

In summary, (2R)-1-[(4S)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene is a powerful chiral ligand that plays a critical role in asymmetric catalysis. Its discovery has enabled the development of highly enantioselective catalytic processes, which are essential for the efficient synthesis of chiral molecules. As a result, this ligand has become an important tool in both academic research and industrial applications, particularly in the field of pharmaceutical synthesis.

References

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