(1S)-1-[(1R)-1-[bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-[bis(4-methoxy-3,5-dimethylphenyl)phosphino]phenyl]ferrocene
[CAS# 565184-34-1]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: (1S)-1-[(1R)-1-[bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-[bis(4-methoxy-3,5-dimethylphenyl)phosphino]phenyl]ferrocene
• Molecular Formula: C₅₂H₄₄F₁₂FeO₂P₂
• Molecular Weight: 1046.68
• CAS Registry Number: 565184-34-1
• SMILES: FC(F)(F)C1=CC(C(F)(F)F)=CC(P(C2=CC(C(F)(F)F)=CC(C(F)(F)F)=C2)[C@@H]([C-]34[Fe+2]56789%10%11([CH-]%12[CH]8=[CH]9[CH]%10=[CH]%11%12)C3(C%13=C(C=CC=C%13)P(C%14=CC(C)=C(C(C)=C%14)OC)C%15=CC(C)=C(C(C)=C%15)OC)=C5([H])[CH]6=C74[H])C)=C1

Discovery and Applications

(1S)-1-[(1R)-1-[bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-[bis(4-methoxy-3,5-dimethylphenyl)phosphino]phenyl]ferrocene is a sophisticated chiral phosphine ligand that plays a crucial role in asymmetric catalysis. Its development represents a significant advance in the field of organometallic chemistry and catalysis due to its unique structural features and high catalytic performance.

This ligand features a ferrocene core, which provides a stable and electronically rich environment for coordination chemistry. The ligand's structure includes two distinct phosphine moieties: one with bis[3,5-bis(trifluoromethyl)phenyl]phosphino groups and the other with bis(4-methoxy-3,5-dimethylphenyl)phosphino groups. The trifluoromethyl groups in the first moiety enhance the electron-withdrawing character, which significantly influences the ligand's electronic properties and its ability to stabilize metal centers. Meanwhile, the methoxy and methyl groups in the second phosphine moiety contribute to the ligand's overall steric and electronic profile, making it highly effective in asymmetric reactions.

The primary application of (1S)-1-[(1R)-1-[bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-[bis(4-methoxy-3,5-dimethylphenyl)phosphino]phenyl]ferrocene is in asymmetric synthesis. This ligand is particularly valuable in asymmetric hydrogenation and cross-coupling reactions, where it enables the precise formation of chiral centers with high enantioselectivity. In asymmetric hydrogenation, it facilitates the production of chiral alcohols and amines, which are important for pharmaceutical synthesis and other fine chemical applications. In cross-coupling reactions, the ligand helps to form complex organic molecules with controlled stereochemistry, making it a powerful tool for creating chiral building blocks in various chemical processes.

The effectiveness of this ligand is attributed to its carefully designed electronic and steric properties, which optimize its performance in catalysis. By influencing the electronic environment around the metal center and providing a suitable steric environment, it enhances the selectivity and efficiency of asymmetric transformations.

In summary, (1S)-1-[(1R)-1-[bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ethyl]-2-[2-[bis(4-methoxy-3,5-dimethylphenyl)phosphino]phenyl]ferrocene is a remarkable advancement in chiral ligand design. Its unique structural features enable it to perform exceptionally well in asymmetric catalysis, contributing to the synthesis of chiral compounds with high precision and efficiency.

References

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