(-)-1,2-Bis((2R,5R)-2,5-dimethylphospholano)benzene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate,(CAS No. 210057-23-1) is a chiral rhodium(I) complex catalyst composed of a Me-DuPHOS chiral diphosphine ligand coordinated with cyclooctadiene (COD) and rhodium(I). It is one of the most widely used catalysts for enantioselective homogeneous hydrogenation, providing excellent activity and high enantioselectivity for a broad range of prochiral substrates.
This catalyst has been extensively applied in asymmetric synthesis, pharmaceutical chemistry, fine chemical production, and catalytic methodology development, particularly for the asymmetric hydrogenation of dehydroamino acids, enamides, enamines, α,β-unsaturated compounds, and functionalized olefins.
The catalyst features:
(R,R)-Me-DuPHOS Rhodium(I) Tetrafluoroborate is widely recognized as one of the most effective catalysts for enantioselective hydrogenation. It has demonstrated excellent catalytic activity and high enantioselectivity in the hydrogenation of:
The catalyst consistently delivers products with high enantiomeric excess (ee) and broad substrate compatibility.
The Me-DuPHOS ligand forms highly efficient rhodium catalytic systems for asymmetric reductive amination, enabling the synthesis of optically active amines with excellent stereoselectivity.
This catalyst has been successfully applied in the enantioselective synthesis of β-amino alcohols and 1,2-diamines, important chiral intermediates used in pharmaceutical synthesis, asymmetric catalysis, and fine chemical production.
Me-DuPHOS-based rhodium catalysts serve as highly effective ligands for the catalytic asymmetric 4+1 cycloaddition of vinylallenes with carbon monoxide (CO), providing efficient access to structurally complex chiral cyclic compounds.
The catalyst is widely employed in Rh-catalyzed asymmetric enyne cycloisomerization, offering high regioselectivity and enantioselectivity for the construction of valuable cyclic frameworks.
Me-DuPHOS-containing catalytic systems have demonstrated excellent performance in the enantioselective addition of dialkylzinc reagents to N-diphenylphosphinoyl imines, enabling efficient synthesis of optically active amines.
The ligand has also been utilized in palladium-catalyzed asymmetric phosphination, providing an efficient approach for the preparation of chiral organophosphorus compounds.
Owing to its outstanding catalytic efficiency and stereocontrol, (R,R)-Me-DuPHOS Rhodium(I) Tetrafluoroborate is widely used in:
| Parameter | Recommended Conditions |
|---|---|
| Reaction Type | Asymmetric hydrogenation |
| Catalyst Loading | Optimized according to substrate |
| Atmosphere | Hydrogen under inert handling conditions |
| Solvent | Alcohols, dichloromethane, THF or other compatible solvents |
| Storage | Store under inert atmosphere in a cool, dry place |
What is CAS 210057-23-1 used for?
It is primarily used as a chiral rhodium catalyst for asymmetric hydrogenation and enantioselective organic synthesis.
Which reactions is this catalyst best suited for?
It is widely employed in the asymmetric hydrogenation of dehydroamino acids, enamides, enamines, and other prochiral unsaturated compounds.
Why is the Me-DuPHOS ligand important?
The chiral Me-DuPHOS ligand creates a well-defined asymmetric environment around the rhodium center, enabling excellent stereochemical control during catalytic reactions.
Can this catalyst be used in pharmaceutical research?
Yes. It is frequently used in the preparation of optically active intermediates and in the development of asymmetric synthetic routes for pharmaceutical compounds.
Is this catalyst compatible with homogeneous catalytic systems?
Yes. It is specifically designed for homogeneous asymmetric catalysis and exhibits excellent activity under optimized reaction conditions.
How should this catalyst be stored?
To maintain catalyst performance, it should be stored in a tightly sealed container under an inert atmosphere and protected from moisture and air.
Is this product intended for research use only?
Yes. This catalyst is supplied for scientific research and laboratory development only.
