(S)-1-{(sp)-2-[2-(Diphenylphosphino)phenyl]ferrocenyl}ethyldi(2-norbornyl)phosphine
[CAS# 849925-45-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (S)-1-{(sp)-2-[2-(Diphenylphosphino)phenyl]ferrocenyl}ethyldi(2-norbornyl)phosphine
• Synonyms: [(1S,4R)-2-bicyclo[2.2.1]heptanyl]-[(1R,4S)-2-bicyclo[2.2.1]heptanyl]-[(1S)-1-[(5E)-5-(6-diphenylphosphanylcyclohexa-2,4-dien-1-ylidene)cyclopenta-1,3-dien-1-yl]ethyl]phosphane cyclopenta-1,3-diene iron(2+)
• Molecular Formula: C₄₄H₄₈FeP₂
• Molecular Weight: 694.64
• CAS Registry Number: 849925-45-7
• SMILES: C[C@@H](C\1=CC=C/C1=C\2/C=CC=C[C-]2P(C3=CC=CC=C3)C4=CC=CC=C4)P(C5C[C@H]6CC[C@@H]5C6)C7C[C@@H]8CC[C@H]7C8.[CH-]1C=CC=C1.[Fe+2]

Discovory and Applicatios

(S)-1-{(sp)-2-[2-(Diphenylphosphino)phenyl]ferrocenyl}ethyldi(2-norbornyl)phosphine is a notable chiral phosphine ligand that has made significant contributions to the field of asymmetric catalysis. This compound, part of the Walphos series of ligands, was designed to enhance the performance of transition metal catalysts in various asymmetric reactions, particularly those requiring high enantioselectivity.

The development of (S)-1-{(sp)-2-[2-(Diphenylphosphino)phenyl]ferrocenyl}ethyldi(2-norbornyl)phosphine reflects advances in ligand design aimed at optimizing the selectivity and efficiency of catalytic processes. The ligand’s structure combines several key elements: a ferrocenyl backbone, a diphenylphosphino group, and a di(2-norbornyl)phosphine moiety. This unique arrangement provides a chiral environment that enhances the catalytic performance of metal complexes formed with this ligand.

One of the primary applications of (S)-1-{(sp)-2-[2-(Diphenylphosphino)phenyl]ferrocenyl}ethyldi(2-norbornyl)phosphine is in asymmetric hydrogenation. In this reaction, the ligand facilitates the addition of hydrogen to unsaturated substrates, resulting in the formation of chiral alcohols or amines. The ligand’s ability to create a highly selective environment around the metal center ensures high enantioselectivity, which is crucial for the production of enantiomerically pure compounds. This application is especially valuable in the pharmaceutical industry, where precise control over stereochemistry is essential for drug development.

The ligand is also used in asymmetric cross-coupling reactions, where it helps form carbon-carbon bonds with high stereoselectivity. These reactions are fundamental in organic synthesis, allowing chemists to build complex molecular structures. The (S)-1-{(sp)-2-[2-(Diphenylphosphino)phenyl]ferrocenyl}ethyldi(2-norbornyl)phosphine ligand stabilizes metal intermediates and directs the formation of specific products, demonstrating its utility in creating intricate organic frameworks.

Overall, the discovery and application of (S)-1-{(sp)-2-[2-(Diphenylphosphino)phenyl]ferrocenyl}ethyldi(2-norbornyl)phosphine highlight the advances in chiral ligand development and their impact on asymmetric catalysis. This ligand exemplifies how tailored design can significantly improve catalytic performance, contributing to both academic research and industrial applications.