[(R)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyl]dicyclohexylphosphine
[CAS# 158923-07-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: [(R)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyl]dicyclohexylphosphine
• Synonyms: (S,S)-1-Dicyclohexylphosphino-2-[1-(dicyclohexylphosphino)ethyl]ferrocene
• Molecular Formula: C₃₆H₅₆FeP₂
• Molecular Weight: 606.62
• CAS Registry Number: 158923-07-0
• SMILES: C[C@@H]([C]1[CH][CH][CH][C]1P(C2CCCCC2)C3CCCCC3)P(C4CCCCC4)C5CCCCC5.[CH]1[CH][CH][CH][CH]1.[Fe]

Discovery and Applications

[(R)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyl]dicyclohexylphosphine is a notable chemical compound recognized for its role in asymmetric catalysis. This chiral ligand features a unique combination of ferrocenyl and dicyclohexylphosphine groups, providing it with distinct properties useful in various catalytic applications.

The compound was first synthesized as part of research aimed at developing highly effective chiral ligands for asymmetric synthesis. Its structure includes a ferrocenyl group, which contributes to its chiral environment, and dicyclohexylphosphine moieties, which enhance the stability and reactivity of the metal complexes it forms.

The discovery of this ligand was motivated by the need for catalysts that could facilitate enantioselective transformations. The introduction of the ferrocenyl group into the ligand framework offers enhanced stereochemical control, making it particularly valuable for asymmetric synthesis where high selectivity is crucial.

In practical applications, [(R)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyl]dicyclohexylphosphine has been employed in various catalytic processes. One of its primary uses is in asymmetric hydrogenation reactions, where it helps in the selective reduction of prochiral compounds to form optically active products. This application is significant in the production of pharmaceuticals and fine chemicals, where the precise control of stereochemistry is essential.

Additionally, this ligand is used in asymmetric carbon-carbon bond-forming reactions, such as in the formation of chiral alcohols and amines. Its effectiveness in these reactions stems from its ability to coordinate with transition metals and influence their reactivity and selectivity.

The development of [(R)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyl]dicyclohexylphosphine highlights the ongoing advancements in chiral ligand design and their impact on asymmetric catalysis. Its unique structure and application in asymmetric synthesis underscore its importance in achieving high levels of enantioselectivity and efficiency in chemical transformations.

References

2022. Addition of Oxygen Nucleophiles. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-144-00043

2022. C—P Bond Forming Reactions. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-237-00115