(S)-(+)-1-[(R)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine
[CAS# 162291-02-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (S)-(+)-1-[(R)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine
• Synonyms: (2S)-1-[(1S)-1-(Dicyclohexylphosphino)ethyl]-2-(diphenylphosphino)ferrocene
• Molecular Formula: C₃₆H₄₄FeP₂
• Molecular Weight: 594.54
• CAS Registry Number: 162291-02-3
• EC Number: 813-041-1
• SMILES: CC([c-]1cccc1P(c2ccccc2)c3ccccc3)P(C4CCCCC4)C5CCCCC5.[cH-]1cccc1.[Fe+2]

Safety Data

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

Discovory and Applicatios

(S)-(+)-1-[(R)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine, commonly known as a chiral ferrocenyl phosphine ligand, is a prominent compound in the field of asymmetric catalysis. This chemical substance has garnered significant attention due to its ability to induce high levels of enantioselectivity in various catalytic reactions, making it invaluable in the synthesis of optically active compounds, particularly in the pharmaceutical industry.

The discovery of (S)-(+)-1-[(R)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine is rooted in the broader context of developing efficient chiral ligands for asymmetric synthesis. The unique structure of this compound, which combines the redox-active ferrocene unit with a bulky dicyclohexylphosphine group, allows for fine-tuning of electronic and steric properties, essential for controlling the outcome of catalytic reactions. This ligand was developed as part of an effort to expand the toolkit available for creating chiral centers in complex molecules.

The key feature of (S)-(+)-1-[(R)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine is its ability to coordinate with transition metals, such as palladium, platinum, or rhodium, to form highly effective catalysts. These metal-ligand complexes have been shown to promote a variety of asymmetric reactions, including hydrogenation, cross-coupling, and addition reactions, with excellent enantioselectivity. The ligand’s chiral nature ensures that the products of these reactions are obtained predominantly in one enantiomeric form, which is crucial for the biological activity of pharmaceuticals.

One of the most notable applications of this ligand is in the asymmetric hydrogenation of prochiral substrates. When complexed with a transition metal, the resulting catalyst can reduce alkenes, imines, and ketones to their corresponding chiral products with high enantiomeric excess. This has profound implications in the pharmaceutical industry, where the production of single-enantiomer drugs is often required to meet regulatory standards and ensure therapeutic efficacy.

In addition to hydrogenation, (S)-(+)-1-[(R)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine has been employed in asymmetric allylic substitution reactions. These reactions are valuable for constructing carbon-carbon and carbon-heteroatom bonds in a stereoselective manner, providing access to a wide range of chiral molecules that can serve as intermediates in the synthesis of complex natural products and active pharmaceutical ingredients.

The ligand’s utility extends to the field of asymmetric cross-coupling reactions, such as the Suzuki-Miyaura and Negishi reactions. In these processes, the ligand’s ability to stabilize the metal center while providing a chiral environment leads to the formation of chiral biaryl or sp3-sp2 carbon frameworks with high selectivity. These reactions are instrumental in the synthesis of compounds with chiral centers, which are often found in drug molecules and materials with specific chiral properties.

The versatility of (S)-(+)-1-[(R)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine has made it a staple in academic and industrial research focused on asymmetric catalysis. Its application has not only streamlined the synthesis of enantiomerically pure compounds but also contributed to the development of new methodologies in organic synthesis. As the demand for chiral compounds continues to grow, especially in the pharmaceutical sector, this ligand’s importance is expected to rise, prompting further exploration of its potential in new catalytic transformations.

In summary, (S)-(+)-1-[(R)-2-(Diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine is a powerful chiral ligand that plays a pivotal role in asymmetric catalysis. Its discovery has enabled the efficient and selective synthesis of chiral molecules, driving advancements in various fields, particularly in the production of pharmaceuticals.