(R)-(-)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine
[CAS# 55700-44-2]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: (R)-(-)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine
• Molecular Formula: C₂₆H₂₈FeNP
• Molecular Weight: 441.33
• CAS Registry Number: 55700-44-2
• EC Number: 633-502-9
• SMILES: C[C@H]([C]1[CH][CH][CH][C]1P(C2=CC=CC=C2)C3=CC=CC=C3)N(C)C.[CH]1[CH][CH][CH][CH]1.[Fe]

Properties

• Melting point: 141-143 ºC
• alpha: -355 º (c=0.6 in EtOH)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H332-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312

Discovory and Applicatios

(R)-(-)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine is a prominent chiral ligand widely used in asymmetric synthesis and catalysis. This compound is valued for its ability to facilitate the formation of enantiomerically enriched products, which is crucial in the synthesis of various fine chemicals and pharmaceuticals. The following article outlines the discovery, synthesis, and applications of this significant chemical substance.

The discovery of (R)-(-)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine is a key milestone in the development of chiral ligands. The compound emerged from the need for highly effective chiral ligands that could provide high selectivity and efficiency in asymmetric catalysis. Researchers aimed to design ligands with optimal steric and electronic properties to enhance the performance of catalytic systems, leading to the synthesis of this compound.

The synthesis of (R)-(-)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine involves a multi-step process. The preparation typically starts with the synthesis of the ferrocenyl phosphine derivative. This is followed by its reaction with N,N-dimethyl-1-ethylamine to yield the final product. The process requires careful control of reaction conditions and purification steps to ensure high enantiomeric purity and yield of the compound. The unique combination of a chiral amine with a diphenylphosphinoferrocenyl group is critical for the compound’s effectiveness in asymmetric synthesis.

One of the primary applications of (R)-(-)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine is as a chiral ligand in asymmetric catalysis. Its ferrocenyl moiety, combined with the diphenylphosphino group, imparts unique steric and electronic properties that enhance the selectivity of catalytic reactions. This enables the formation of highly enantioenriched products, which is essential for the synthesis of complex molecules in pharmaceuticals and fine chemicals. The compound's effectiveness in asymmetric synthesis makes it a valuable tool in both academic research and industrial applications.

In addition to its role in asymmetric synthesis, (R)-(-)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine is used in various catalytic processes involving transition metals. It forms stable complexes with metals such as palladium and rhodium, facilitating a range of reactions including cross-coupling, hydrogenation, and other transformations. The stability and reactivity of these metal-ligand complexes contribute to the efficiency and selectivity of the catalytic processes.

The compound is also known for its robustness and ease of handling. It is typically handled under standard laboratory conditions, with appropriate safety measures including the use of personal protective equipment. Its stability under various conditions makes it a reliable reagent for ongoing research and application in catalysis.

Future research on (R)-(-)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine may explore its potential in new catalytic systems and further optimization of its performance. Continued advancements in the design and application of chiral ligands will likely enhance the compound's utility in diverse areas of chemical synthesis and industrial processes.

References

2001. From 1-Ferrocenyl-N,N-dimethylethylamine. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-001-00879

2009. Approaches to Enantioselective Catalysts. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-042-00462

2010. 1,2-Disubstituted E-Alkenes via β-Monosubstituted E-Alkenyl Derivatives. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-047-00405