(R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene
[CAS# 565184-30-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene
• Molecular Formula: C₃₈H₄₄FeP₂
• Molecular Weight: 618.55
• CAS Registry Number: 565184-30-7
• SMILES: C[C@@H](P(C(C)(C)C)C(C)(C)C)[C-]1(C2(C3=CC=CC(P(C4=CC=CC=C4)C5=CC=CC=C5)=C3)=C6([H])C7([H])=C81)[Fe+2]9%10%11%122678[C-]%13C9=C%10C%11=C%13%12

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

(R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene is a prominent example of a chiral phosphine ligand used in advanced organometallic chemistry. This compound was developed to enhance the performance of asymmetric catalysis, a crucial area in synthetic chemistry.

The discovery of this ligand stemmed from the need for highly efficient and selective catalysts for asymmetric reactions. The ligand's design incorporates a ferrocene core, which is a well-known structural unit in organometallic chemistry. Ferrocene, a sandwich compound consisting of two cyclopentadienyl rings bound to a central iron atom, provides stability and unique electronic properties to the ligand. Attached to this core are two distinct phosphine groups: a di-tert-butylphosphino group and a diphenylphosphino group, each contributing to the ligand's effectiveness.

The (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene ligand is primarily employed in asymmetric catalysis to facilitate high-precision chemical reactions. Its chiral nature ensures that it can induce high enantioselectivity in various reactions, leading to the production of chiral products with excellent optical purity. This property is particularly valuable in the synthesis of pharmaceuticals, where chirality is crucial for the biological activity of the compounds.

One notable application of this ligand is in asymmetric hydrogenation, where it helps achieve high enantioselectivity in the hydrogenation of alkenes to produce chiral alcohols. Additionally, the ligand is used in other asymmetric transformations, such as the synthesis of chiral amines and other fine chemicals.

In summary, (R)-1-[(R)-1-(Di-tert-butylphosphino)ethyl]-2-[2-(diphenylphosphino)phenyl]ferrocene is a highly effective chiral phosphine ligand that has significantly advanced the field of asymmetric catalysis. Its unique structure and properties make it a valuable tool for achieving high enantioselectivity in synthetic chemistry.

References

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