(1S)-1-[Bis(tert-butyl)phosphino]-2-[(1S)-1-[bis(2-methylphenyl)phosphino]ethyl]ferrocene
[CAS# 849924-77-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (1S)-1-[Bis(tert-butyl)phosphino]-2-[(1S)-1-[bis(2-methylphenyl)phosphino]ethyl]ferrocene
• Synonyms: (S)-1-[(R)-2-(Di-tert.-butylphosphino)ferrocenyl]ethylbis(2-methylphenyl)phosphi
• Molecular Formula: C₃₄H₄₄FeP₂
• Molecular Weight: 570.51
• CAS Registry Number: 849924-77-2
• SMILES: [Fe+2].C[C@@H](C1C=C[CH-]C=1P(C(C)(C)C)C(C)(C)C)P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH-]1C=CC=C1

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P280-P305+P351+P338

Discovory and Applicatios

(1S)-1-[Bis(tert-butyl)phosphino]-2-[(1S)-1-[bis(2-methylphenyl)phosphino]ethyl]ferrocene, commonly known as a chiral bidentate phosphine ligand, represents a significant advancement in the field of asymmetric catalysis. This compound is designed to improve the efficiency and selectivity of transition metal-catalyzed reactions by providing a highly specific chiral environment.

The discovery of this ligand involved the synthesis of a new type of chiral phosphine complex, integrating both bulky tert-butyl groups and electron-rich 2-methylphenyl groups to achieve optimal steric and electronic properties. The synthesis typically requires a careful approach, combining ferrocene as a backbone with phosphine groups in a manner that ensures high purity and stability of the final product. The (1S)-configuration is crucial as it imparts the desired stereochemical control necessary for asymmetric transformations.

The primary application of (1S)-1-[Bis(tert-butyl)phosphino]-2-[(1S)-1-[bis(2-methylphenyl)phosphino]ethyl]ferrocene lies in asymmetric hydrogenation. In this reaction, the ligand coordinates with transition metals such as rhodium or ruthenium to form active catalytic complexes. The unique structure of the ligand provides a chiral environment that directs the hydrogenation process, leading to high enantioselectivity in the formation of chiral products. This capability is particularly valuable in the pharmaceutical industry, where precise control over stereochemistry is essential for the synthesis of chiral drugs.

Beyond hydrogenation, this ligand has demonstrated utility in other asymmetric transformations, including asymmetric alkylation and allylic substitution reactions. Its ability to stabilize the metal center while providing a chiral environment allows for enhanced control over reaction outcomes, making it a versatile tool in organic synthesis.

The ligand's effectiveness is attributed to its dual phosphine functionality combined with the ferrocene core, which provides both electronic and steric influences. The tert-butyl groups offer substantial steric protection, reducing unwanted side reactions and improving the selectivity of the catalytic process. Meanwhile, the 2-methylphenyl groups contribute to the ligand's ability to engage in precise chiral interactions with the metal center.

In addition to its applications in traditional organic synthesis, (1S)-1-[Bis(tert-butyl)phosphino]-2-[(1S)-1-[bis(2-methylphenyl)phosphino]ethyl]ferrocene holds promise for future developments in material science and other specialized fields. Its ability to impart specific chiral properties to materials could lead to new applications in creating functional materials with unique optical or electronic characteristics.

Overall, the development of (1S)-1-[Bis(tert-butyl)phosphino]-2-[(1S)-1-[bis(2-methylphenyl)phosphino]ethyl]ferrocene represents a notable advancement in chiral ligand design. Its introduction has significantly enhanced the capabilities of asymmetric catalysis, providing chemists with a powerful tool for achieving high enantioselectivity in a range of chemical processes.