(4S)-2-(2-(Diphenylphosphino)phenyl)-4-isopropyl-4,5-dihydrooxazole
[CAS# 148461-14-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Phosphine ligand
• Name: (4S)-2-(2-(Diphenylphosphino)phenyl)-4-isopropyl-4,5-dihydrooxazole
• Synonyms: diphenyl-[2-[(4S)-4-propan-2-yl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]phosphane
• Molecular Formula: C₂₄H₂₄NOP
• Molecular Weight: 373.43
• CAS Registry Number: 148461-14-7
• SMILES: CC(C)[C@H]1COC(=N1)C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4

Properties

• Solubility: Insoluble (2.7E^-4 g/L) (25 ºC), Calc.^*
• Melting point: 85-90 ºC

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

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

(4S)-2-(2-(Diphenylphosphino)phenyl)-4-isopropyl-4,5-dihydrooxazole is a notable chemical compound in the field of organophosphorus chemistry, distinguished by its unique structural features and versatile applications. This compound combines a chiral oxazole framework with a diphenylphosphine group, resulting in a molecule with significant potential for use in various chemical and industrial processes.

The discovery of (4S)-2-(2-(Diphenylphosphino)phenyl)-4-isopropyl-4,5-dihydrooxazole emerged from efforts to design and synthesize novel ligands for catalytic processes. The oxazole ring, which is a five-membered heterocyclic compound containing both nitrogen and oxygen, is known for its stability and versatility in forming coordination complexes. By incorporating the diphenylphosphine group, researchers aimed to enhance the ligand's ability to stabilize metal centers and facilitate catalytic transformations.

Synthesis of (4S)-2-(2-(Diphenylphosphino)phenyl)-4-isopropyl-4,5-dihydrooxazole typically involves the reaction of an appropriate oxazole derivative with diphenylphosphine, followed by the introduction of the isopropyl group. The chiral nature of the oxazole ring is crucial, as it imparts stereochemical control to the compound, making it particularly valuable in asymmetric synthesis.

One of the primary applications of (4S)-2-(2-(Diphenylphosphino)phenyl)-4-isopropyl-4,5-dihydrooxazole is as a chiral ligand in asymmetric catalysis. The compound's ability to form stable complexes with transition metals, such as palladium or rhodium, makes it an effective catalyst for various enantioselective reactions. These reactions are essential for the synthesis of chiral molecules, which are valuable in the production of pharmaceuticals and agrochemicals. The stereochemical control provided by the ligand helps to achieve high levels of enantioselectivity, leading to the formation of desired chiral products with minimal by-products.

Additionally, (4S)-2-(2-(Diphenylphosphino)phenyl)-4-isopropyl-4,5-dihydrooxazole finds applications in the development of novel materials. The compound's coordination chemistry can be leveraged to create new materials with tailored properties, such as conducting polymers or advanced catalysts. Its ability to stabilize various metal centers makes it a versatile tool for material scientists seeking to design materials with specific functional properties.

In summary, (4S)-2-(2-(Diphenylphosphino)phenyl)-4-isopropyl-4,5-dihydrooxazole represents a significant advancement in the field of organophosphorus chemistry. Its discovery has provided a valuable ligand for asymmetric catalysis and material science, offering new possibilities for the synthesis of chiral compounds and the development of innovative materials. The compound's unique structural features and applications underscore its importance in both academic research and industrial processes.

References

2021. (4+1)-Cycloadditions Exploiting the Biphilicity of Oxyphosphonium Enolates and RhII/PdII-Stabilized Metallocarbenes for the Construction of Five-Membered Frameworks. Synlett, 32(5).
DOI: 10.1055/s-0040-1706009

2016. Recent Developments in Asymmetric Allylic Amination Reactions. Synthesis, 48(12).
DOI: 10.1055/s-0035-1562090

2002. Diastereoselective formation of chiral iridium hydrides containing the chiral P,N-chelate ligand (4S)-2-(2-(diphenylphosphino)phenyl)-4-isopropyl-1,3-oxazoline. Chemical Communications, (7).
DOI: 10.1039/b200518b