505092-86-4

Basic information

• Product Name: (-)-2,3-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANYL]MALEIC ANHYDRIDE
• Synonyms: (-)-2,3-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANYL]MALEIC ANHYDRIDE;CATASIUM(R) M(R);(-)-2,3-Bis[(2R,5R)-2,5-dimethylphospholano]maleic anhydride;(-)-2,3-Bis[(2R,5R)-2,5-dimethylphospholanyl]maleicanhydride,min.97%[catASiumM(R)];catASium(R) M(R), 3,4-Bis[(2R,5R)-2,5-dimethyl-1-phospholanyl]furan-2,5-dione;catASium? M(R)
• CAS NO: 505092-86-4
• Molecular Formula: C16H24O3P2
• Molecular Weight: 326.31
• Product Categories: organophosphine ligand
• Mol File: 505092-86-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• BRN: 9428339
• CAS DataBase Reference: (-)-2,3-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANYL]MALEIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-2,3-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANYL]MALEIC ANHYDRIDE(505092-86-4)
• EPA Substance Registry System: (-)-2,3-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANYL]MALEIC ANHYDRIDE(505092-86-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 505092-86-4(Hazardous Substances Data)

Usage

General Description

(-)-2,3-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANYL]MALEIC ANHYDRIDE is a chiral organophosphorus compound that is commonly used as a stereoselective catalyst in organic synthesis reactions. It is characterized by its two phospholane rings and maleic anhydride moiety, which impart unique stereochemical properties. (-)-2,3-BIS[(2R,5R)-2,5-DIMETHYLPHOSPHOLANYL]MALEIC ANHYDRIDE has been widely utilized in asymmetric catalysis and is known for its ability to facilitate a variety of enantioselective transformations. Its use in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals has made it an important and valuable tool in the field of chemical synthesis.

Upstream product

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

Relevant articles and documents

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.

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.