505092-86-4

Usage

Uses

Used in Pharmaceutical Industry:
(-)-2,3-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANYL]MALEIC ANHYDRIDE is used as a stereoselective catalyst for the synthesis of pharmaceuticals, enabling the production of enantiomerically pure compounds, which is crucial for the development of effective and safe drugs.
Used in Agrochemical Industry:
In the agrochemical industry, (-)-2,3-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANYL]MALEIC ANHYDRIDE is used as a catalyst for the synthesis of enantioselective agrochemicals, ensuring the production of active ingredients with desired chiral properties for improved performance and reduced environmental impact.
Used in Fine Chemicals Synthesis:
(-)-2,3-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANYL]MALEIC ANHYDRIDE is employed as a catalyst in the synthesis of various fine chemicals, facilitating enantioselective transformations to produce high-quality specialty chemicals for a range of applications, including fragrances, flavors, and other high-value products.

Upstream product

• 1122-17-4 dichloromaleic acid anhydride 
• 505092-85-3 (2R,5R)-2,5-dimethyl-1-(trimethylsilyl)phospholane 
• 866025-84-5 (2S,5S)-2,5-dimethyl-1-(trimethylsilyl)phospholane 

Relevant academic research and scientific papers

A highly tunable family of chiral bisphospholanes for Rh-catalyzed enantioselective hydrogenation reactions

A set of 16 new and closely related bisphospholane ligands have been prepared by using a highly flexible and convergent approach. Each synthesis can be performed on an industrially relevant scale. The bisphosphines differ in the nature of the bridge connecting both phospholane units. Bridges are formed by three-, four-, five- and six-membered heterocyclic or alicyclic rings. Bisphospholanes and their Rh-precatalysts have been investigated by using results of theoretical calculations (DFT) and analytic measurements ( 31P and 103Rh NMR spectroscopy, X-ray structure analysis). The studies showed that catalysts based on ligands with maleic anhydride or maleimide bridges give constantly superior enantioselectivities in methanol as the solvent. This may account for optimised steric and electronic effects. However, by changing the solvent catalysts with other backbones can give rise to excellent results. This gives proof that simple correlations between steric and electronic properties and results in the enantioselective hydrogenation frequently claimed in literature are not general.

PROCESS FOR PREPARING BISPHOSPHOLANE LIGANDS

The present invention is directed at a process for preparing enantiomerically enriched compounds of the general formula (I). Compounds of the type shown are employed in catalyst systems.

Synthesis of a new chiral bisphospholane ligand for the Rh(I)-catalyzed enantioselective hydrogenation of isomeric β-acylamido acrylates

The highly stereoselective synthesis of a chiral silylphospholane has been described, which can be advantageously used as a building block under base-free conditions for the construction of diphosphines related to DuPHOS. The utility of silylphospholane is shown in the synthesis of a new bisphospholane ligand 1 (MalPHOS), which is characterized by a maleic anhydride backbone. The ligand forms with Rh(I) a complex with a larger bite angle P-Rh-P than the analogue Me-DuPHOS complex. Both complexes have been tested in the asymmetric hydrogenation of unsaturated α- and β-amino acid precursors of pharmaceutical relevance. In several cases, the new catalyst was superior in comparison to the Me-DuPHOS complex, in particular when (Z)-configured β-acylamido acrylates were used as substrates.