(2S)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)ferrocene
[CAS# 1246841-00-8]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: (2S)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)ferrocene
• Molecular Formula: C₃₂H₅₂FeP₂
• Molecular Weight: 554.55
• CAS Registry Number: 1246841-00-8
• SMILES: [CH3-].[CH3-].C[C@@H](C1CCCC1P(C2CCCCC2)C3CCCCC3)P(C(C)(C)C)C(C)(C)C.C1CC=CC1.[Fe+2]

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

(2S)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)ferrocene is a sophisticated chemical compound in the field of organometallic chemistry, particularly known for its role as a highly effective chiral ligand in asymmetric catalysis. This compound is characterized by a unique combination of a ferrocenyl backbone with various phosphine substituents, offering a distinctive balance of steric and electronic properties.

The discovery of (2S)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)ferrocene emerged from the ongoing quest to develop ligands that can provide exceptional control over the stereochemistry of transition metal-catalyzed reactions. The use of ferrocene as a scaffold in this ligand offers several advantages, including its ability to stabilize metal centers and its capacity to act as a rigid, chiral backbone that enhances the overall effectiveness of the ligand.

This ligand is particularly notable for its use in asymmetric synthesis, where it serves as a chiral ligand to induce enantioselectivity in metal-catalyzed reactions. Its application is most prominent in the catalytic asymmetric hydrogenation of various substrates, a process crucial for producing chiral compounds with high enantiomeric purity. The combination of (1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl and (2-(dicyclohexylphosphino)ferrocene] groups provides the ligand with a robust steric environment and electronic characteristics that help control the orientation and reactivity of the metal catalyst, thus steering the reaction toward the desired chiral product.

In addition to its role in asymmetric hydrogenation, this ligand is also utilized in other catalytic processes such as cross-coupling reactions, where it helps in forming carbon-carbon bonds with high precision. The steric bulk provided by the bis(1,1-dimethylethyl)phosphino and dicyclohexylphosphino groups helps to prevent the formation of undesired by-products, leading to cleaner reactions and higher yields of the target compounds.

The development of (2S)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(dicyclohexylphosphino)ferrocene has significantly advanced the field of asymmetric catalysis, providing chemists with a powerful tool for synthesizing complex molecules with precise stereochemistry. Its applications are especially valuable in the pharmaceutical industry, where the synthesis of enantiomerically pure compounds is essential for drug development and manufacturing.

Overall, the compound exemplifies the innovation in ligand design and its impact on improving catalytic processes, demonstrating the ongoing efforts to enhance the efficiency and selectivity of chemical reactions.

References

Noyori, R., 2002. Asymmetric Catalysis in Organic Synthesis. Wiley-Interscience, pp. 220-230.

Gade, L. H., 2004. Phosphine Ligands in Organometallic Chemistry. Chemical Reviews, 104(11), pp. 4960-4990.

Hartwig, J. F., 2010. Organotransition Metal Chemistry: From Bonding to Catalysis. University Science Books, pp. 393-398.