(S)-1-{(SP)-2-[2-(Diphenylphosphino)phenyl]Ferrocenyl}ethyldicyclohexylphosphine
[CAS# 849925-19-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (S)-1-{(SP)-2-[2-(Diphenylphosphino)phenyl]Ferrocenyl}ethyldicyclohexylphosphine
• Synonyms: 1,2,3,4,5-Cyclopentanepentayl, compd. with 1-[(1S)-1-(dicyclohexylphosphino)ethyl]-2-[2-(diphenylphosphino)phenyl]-1,2,3,4,5-cyclopentanepentayl, iron salt (1:1:1)
• Molecular Formula: C₄₂H₄₈FeP₂
• Molecular Weight: 670.62
• CAS Registry Number: 849925-19-5
• SMILES: CC([C]1[CH][CH][CH][C]1C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4)P(C5CCCCC5)C6CCCCC6.[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

(S)-1-{(SP)-2-[2-(Diphenylphosphino)phenyl]ferrocenyl}ethyldicyclohexylphosphine is a highly specialized chiral phosphine ligand that plays a crucial role in asymmetric catalysis. Its development and application highlight significant advancements in the field of chiral catalysis and organometallic chemistry.

This ligand features a unique structural framework comprising a chiral ferrocene core, which is pivotal in imparting high stereoselectivity. The ligand’s structure integrates a diphenylphosphino group and a dicyclohexylphosphine group attached to a ferrocenyl backbone. The combination of these elements contributes to the ligand's distinctive properties, making it valuable in various catalytic processes.

The discovery of (S)-1-{(SP)-2-[2-(Diphenylphosphino)phenyl]ferrocenyl}ethyldicyclohexylphosphine stems from the need to enhance the efficiency and selectivity of asymmetric reactions. The chiral ferrocene backbone provides a rigid and well-defined environment, which is essential for achieving high enantioselectivity in catalytic processes. The ligand’s stereochemistry is critical, as it determines the spatial arrangement of substituents around the central metal atom, influencing the outcome of the reaction.

One of the primary applications of this ligand is in asymmetric hydrogenation reactions. Hydrogenation, a process used to reduce unsaturated compounds to their saturated counterparts, benefits significantly from the use of chiral phosphine ligands. The ligand enhances the selectivity of the reaction, allowing for the production of optically active compounds with precise control over their stereochemistry. This application is particularly valuable in the pharmaceutical industry, where the synthesis of chiral drugs requires high enantioselectivity.

In addition to hydrogenation, (S)-1-{(SP)-2-[2-(Diphenylphosphino)phenyl]ferrocenyl}ethyldicyclohexylphosphine is employed in asymmetric cross-coupling reactions. These reactions are essential for the formation of carbon-carbon bonds in organic synthesis. The ligand facilitates the formation of chiral products by improving the selectivity of the metal-catalyzed coupling process. This application is crucial for the synthesis of complex organic molecules used in various fields, including materials science and drug development.

The effectiveness of this ligand in asymmetric catalysis is attributed to its ability to form stable and reactive complexes with transition metals. The chiral environment provided by the ligand ensures high levels of enantioselectivity, which is essential for producing high-purity chiral compounds. This capability underscores the importance of (S)-1-{(SP)-2-[2-(Diphenylphosphino)phenyl]ferrocenyl}ethyldicyclohexylphosphine in advancing the field of asymmetric synthesis and expanding the possibilities for designing new catalytic processes.

Overall, the development and application of (S)-1-{(SP)-2-[2-(Diphenylphosphino)phenyl]ferrocenyl}ethyldicyclohexylphosphine represent significant progress in the field of chiral catalysis. Its unique structure and ability to enhance selectivity in various reactions highlight its importance as a tool for synthesizing complex and valuable organic compounds.