(R)-(+)-1-[(R)-2-(2'-Diphenylphosphinophenyl)ferrocenyl]ethyldiphenylphosphine
[CAS# 565184-32-9]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: (R)-(+)-1-[(R)-2-(2'-Diphenylphosphinophenyl)ferrocenyl]ethyldiphenylphosphine
• Synonyms: Cyclopentane [2-[2-(1-diphenylphosphanylethyl)cyclopentyl]phenyl]-diphenylphosphane iron
• Molecular Formula: C₄₂H₄₆FeP₂
• Molecular Weight: 668.61
• CAS Registry Number: 565184-32-9
• EC Number: 815-159-9
• SMILES: CC(C1CCCC1C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4)P(C5=CC=CC=C5)C6=CC=CC=C6.C1CCCC1.[Fe]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovory and Applicatios

(R)-(+)-1-[(R)-2-(2'-Diphenylphosphinophenyl)ferrocenyl]ethyldiphenylphosphine is a sophisticated chiral phosphine ligand that has significantly impacted asymmetric catalysis in organic synthesis. This compound exemplifies the advancements in ligand design for achieving high enantioselectivity in various catalytic reactions.

The discovery of (R)-(+)-1-[(R)-2-(2'-Diphenylphosphinophenyl)ferrocenyl]ethyldiphenylphosphine was driven by the need for highly effective ligands that could provide precise control over stereochemistry in asymmetric synthesis. The ligand features a ferrocene backbone, a well-known organometallic moiety, which imparts stability and unique electronic properties. The ferrocene core is flanked by two distinct phosphine groups: a diphenylphosphine group and a phosphine group with a substituted phenyl ring. This structure enhances the ligand's ability to coordinate with metal centers and influences the selectivity of the catalytic processes.

In asymmetric catalysis, (R)-(+)-1-[(R)-2-(2'-Diphenylphosphinophenyl)ferrocenyl]ethyldiphenylphosphine is used to catalyze a range of reactions, including asymmetric hydrogenation and cross-coupling reactions. The chiral nature of this ligand allows it to induce high levels of enantioselectivity, making it particularly valuable for synthesizing chiral compounds with high optical purity. These chiral compounds are crucial in the pharmaceutical industry, where the enantiomeric purity of drugs can significantly affect their efficacy and safety.

One prominent application of this ligand is in the asymmetric hydrogenation of alkenes, where it helps produce chiral alcohols with excellent enantioselectivity. Additionally, it is employed in various cross-coupling reactions to create complex molecules with high precision.

Overall, (R)-(+)-1-[(R)-2-(2'-Diphenylphosphinophenyl)ferrocenyl]ethyldiphenylphosphine represents a significant advancement in ligand chemistry. Its unique structure and high performance in asymmetric catalysis underscore its importance in modern organic synthesis and the production of chiral pharmaceuticals.