127797-02-8

Basic information

• Product Name: (-)-MOD-DIOP
• Synonyms: (-)-MOD-DIOP
• CAS NO: 127797-02-8
• Molecular Formula: C₄₃H₅₆O₆P₂
• Molecular Weight: 730.848662
• Mol File: 127797-02-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (-)-MOD-DIOP(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-MOD-DIOP(127797-02-8)
• EPA Substance Registry System: (-)-MOD-DIOP(127797-02-8)

Safety Data

• Hazardous Substances Data: 127797-02-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
(-)-MOD-DIOP is used as a chiral ligand for enantioselective catalysis in various asymmetric synthesis reactions, such as transition metal-catalyzed allylic substitution, Suzuki-Miyaura coupling, and hydrogenation. It is employed for its ability to control the stereochemistry of reactions, enabling the synthesis of complex organic molecules with high enantiomeric purity.
Used in Pharmaceutical Industry:
(-)-MOD-DIOP is used as a chiral ligand in the development of pharmaceutical compounds, where enantioselective catalysis is crucial for the synthesis of enantiomerically pure drugs. Its ability to control the stereochemistry of reactions ensures the production of the desired enantiomer, which is essential for the biological activity and safety of the final drug product.
Used in Chemical Research:
(-)-MOD-DIOP is used as a research tool in the study of asymmetric catalysis and the development of new synthetic methods. Its unique structure and stereochemical properties make it an important reagent for understanding the mechanisms of enantioselective reactions and for designing new chiral ligands with improved performance.

Upstream product

• 122708-97-8 bis(4-methoxy-3,5-dimethylphenyl)-phosphine 
• 37002-45-2 (4S,5S)-2,2-dimethyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolan 
• 51064-65-4 1,4-di-o-tosyl-2,3-isopropylidene-D-threitol 

Relevant articles and documents

Hydroformylation process

A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of a solvent and a catalyst system comprising a rhodium complex and a 2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis[bis(3,5-di-n-alkylphenyl)phosphino]butane. The process gives high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde.

Efficient Asymmetric Syntheses of Naturally Occurring Lignan Lactones Using Catalytic Asymmetric Hydrogenation as a Key Reaction

Optically pure (R)-arylmethylsuccinic acid mono-methyl esters were obtained efficiently by using the catalytic asymmetric hydrogenation of arylidenesuccinic acid monoesters with a rhodium(I) complex of a chiral bisphosphine, (4S,5S)-MOD-DIOP.Asymmetric total syntheses of some naturally occurring lignans, (+)-collinusin, (-)-deoxypodophyllotoxin, and (+)-neoisostegane, were achieved via several steps from (R)-γ-butyrolactones as key intermediates obtained by reduction of (R)-arylmethylsuccinic acid mono methyl-esters.

Synthesis of efficient chiral bisphosphine ligands, modified DIOPs, (4R,5R)-4-(Diaryl- or dialkylphosphino)methyl-5-(diarylphosphino)methyl-2,2- dimethyl-1,3-dioxolanes, and their use in rhodium(I)-catalyzed asymmetric hydrogenations

Modified DIOPs, (4R,5R)-4-(diaryl- or dialkyphosphino)methyl-5- (diarylphosphino)methyl-2,2-dimethyl-1,3-dioxolanes, were prepared on the basis of our design concept, and used as ligands for the rhodium(I)-catalyzed asymmetric hydrogenations of ketopantolactone, itaconic acid, dimethyl itaconate, and β-aryl-substituted itaconic acid derivatives. A neutral rhodium(I)-complex of (4R-trans)-dicyclohexyl[[5- [(diphenylphosphino)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]phosphine (DIOCP) bearing both a dicyclohexylphosphino group and a diphenylphosphino group was found to be a more efficient catalyst than the original DIOP in the asymmetric hydrogenation of ketopantolactone. Modified DIOPs bearing electron-donating groups at their para positions were efficient ligands for the rhodium(I)-catalyzed assymetric hydrogenations of itaconic acid and its derivatives; in particular, (4R-trans)-[(2,2-dimethyl-1,3-dioxolane-4,5- diyl)bis(methylene)]bis[bis(4'-methoxy-3',5'-dimethylphenyl)phosphine] (MOD- DIOP) bearing both a p-methoxy group and two m,m'-methyl groups on each phenyl group showed much higher enantioselectivity and catalytic activity than DIOP.

HIGHLY EFFICIENT ASYMMETRIC HYDROGENATION OF ITACONIC ACID DERIVATIVES CATALYZED BY A MODIFIED DIOP-RHODIUM COMPLEX

A modified DIOP analogue bearing 4-methoxy and 3,5-dimethyl groups on each phenyl group has been synthesized.The rhodium complex of the ligand has been found to give very high optical yields in the asymmetric hydrogenation of itaconic acid and its derivatives bearing β-aryl groups, the products of which are key-intermediates for optically active lignan derivatives.