(2S)-1-[(4R)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene
[CAS# 1065474-88-5]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: (2S)-1-[(4R)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene
• Synonyms: (2Rp)-1-[(4R)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene
• Molecular Formula: C₂₈H₂₈FeNOP
• Molecular Weight: 481.35
• CAS Registry Number: 1065474-88-5
• 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 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

(2S)-1-[(4R)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene, commonly referred to as a ferrocene-based phosphino-oxazoline ligand, is a chiral organometallic compound that has made a significant impact in asymmetric catalysis. The discovery of this compound was driven by the need for effective chiral ligands in the synthesis of enantiomerically pure compounds, which are crucial in pharmaceuticals and other fine chemicals.

The compound features a ferrocene backbone, which is known for its stability and versatility in organometallic chemistry. Attached to the ferrocene core is a chiral oxazoline ring and a diphenylphosphino group, which together provide a unique combination of steric and electronic properties that enhance its catalytic performance. The chirality of the ligand plays a crucial role in inducing asymmetry in catalytic reactions, allowing for the selective formation of one enantiomer over the other.

(2S)-1-[(4R)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene has been widely applied in asymmetric hydrogenation, where it has demonstrated high enantioselectivity in the reduction of various prochiral substrates. This is particularly valuable in the production of chiral alcohols, amines, and other functionalized molecules that are often key intermediates in the synthesis of active pharmaceutical ingredients.

Beyond hydrogenation, this ferrocene-based ligand has also been employed in asymmetric allylic substitution, where it enables the enantioselective substitution of allylic substrates. This reaction is important in the construction of complex chiral molecules, often used in the development of drugs and natural products. The ligand's ability to promote these reactions with high selectivity and efficiency has made it a favored choice among chemists working in asymmetric synthesis.

In summary, (2S)-1-[(4R)-4,5-Dihydro-4-(1-methylethyl)-2-oxazolyl]-2-(diphenylphosphino)ferrocene is a powerful chiral ligand that has significantly advanced the field of asymmetric catalysis. Its applications in hydrogenation and allylic substitution highlight its utility in the synthesis of enantiomerically pure compounds, making it a valuable tool in both academic research and industrial processes.

References

none