130272-52-5

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-dimethyl-2-benzyl-succinate is used as a building block in organic synthesis for the production of various drugs and biologically active compounds. Its chiral nature allows for the creation of enantiomerically pure compounds, which is crucial for the development of effective and safe medications.
Used in Materials Science:
In the field of materials science, (R)-(+)-dimethyl-2-benzyl-succinate is utilized for its potential applications in creating new materials with specific properties. Its unique structure can contribute to the development of materials with tailored characteristics for various applications.
Used as a Chiral Ligand in Asymmetric Catalysis:
(R)-(+)-dimethyl-2-benzyl-succinate is employed as a chiral ligand in asymmetric catalysis, a process that is vital for the synthesis of enantiomerically pure compounds. Its use in this field can enhance the selectivity and efficiency of catalytic reactions, leading to the production of desired enantiomers with high purity, which is essential in the synthesis of pharmaceuticals and other chiral molecules.

InChI:InChI=1/C13H16O4/c1-16-12(14)9-11(13(15)17-2)8-10-6-4-3-5-7-10/h3-7,11H,8-9H2,1-2H3/t11-/m1/s1

Upstream product

• 35262-43-2 dimethyl 2-benzylsuccinate 
• 186581-53-3 diazomethane 
• 67-56-1 methanol 
• 193147-43-2 (R)-3-Benzyl-pent-4-enenitrile 
• 65859-90-7 dimethyl (E)-benzylidenesuccinate 
• 21307-97-1 (R)-2-benzylsuccinic acid 
• 201230-82-2 carbon monoxide 
• 5669-19-2 2-Benzyl-2-propenoic acid 
• 100-39-0 benzyl bromide 
• 6613-41-8 ethyl 3-phenylpyruvate 
• 20593-63-9 2-Benzylacrylic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 125702-14-9 (E)-3-(methoxycarbonyl)-4-phenylbut-3-enoic acid 
• 5653-88-3 trans-phenylitaconic acid 

Downstream Products

• 126121-83-3 (R)-2-benzyl-5-cyano-4-oxopentanoic acid 
• 21307-97-1 (R)-2-benzylsuccinic acid 
• 136282-52-5 N-<(R)-2-benzyl-5-cyano-4-oxopentanoyl>-L-phenylalanine methyl ester 
• 136282-56-9 N-<(R)-2-benzyl-5-cyano-4-oxopentanoyl>-L-phenylalanine 

Relevant academic research and scientific papers

Hydrogen bonding makes a difference in the rhodium-catalyzed enantioselective hydrogenation using monodentate phosphoramidites

A new generation of monodentate phosphoramidite ligands bearing a primary amine moiety was found to display comparable or better efficiency than bisphosphines in the Rh-catalyzed asymmetric hydrogenation of challenging substrates, such as (Z)-methyl α-ace

Palladium-Catalyzed Asymmetric Hydroesterification of α-Aryl Acrylic Acids to Chiral Substituted Succinates

A palladium-catalyzed asymmetric hydroesterification of α-aryl acrylic acids with CO and alcohol was developed, preparing a variety of chiral α-substituted succinates in moderate yields with high ee values. The kinetic profile of the reaction progress revealed that the alkene substrate first underwent the hydroesterification followed by esterification with alcohol. The origin of the enantioselectivity was elucidated by density functional theory computation.

Modular 1,1′-Ferrocenediyl-cored P-Stereogenic Diphosphines: ′′JDayPhos′′ Series and its Use in Rhodium(I)-Catalyzed Hydrogenation

A novel ferrocene-based P-stereogenic diphospine ligand series dubbed JDayPhos was developed, which rhodium(I) complexes of some of its members exhibited excellent enantioselectivity (up to >99% ee) and high activity in asymmetric hydrogenation of β-unsubstituted or -substituted itaconates and α-methylene-γ-oxo-carboxylates. (Figure presented.).

Stitching phospholanes together piece by piece: New modular di- and tridentate stereodirecting ligands

The modular one-pot synthesis of a large family of bi- and tridentate 2,5-dimethyl- and 2,5-diphenyl-substituted phospholanes employs air-stable chiral phospholanium chloride salts and primary amines or NH4Cl as starting materials. These were t

Synthesis and application of phosphinoferrocenylaminophosphine ligands for asymmetric catalysis

(Chemical Equation Presented) A new class of bidentate ligands utilizing a phosphine-aminophosphine structure has been prepared on a ferrocenylethyl backbone in a straightforward and scalable fashion from acetylferrocene. The unique property of the α-ferrocenyl carbonium ion that allows the replacement of a variety of "leaving groups" with retention of configuration greatly facilitates the synthesis, and a number of ligands have been prepared by varying the nitrogen and phosphorus substituents on the aminophosphine. These readily prepared phosphinoferrocenylaminophosphines, known as BoPhoz ligands, show surprising hydrolytic and air stability, with no degradation after 3 years open to the air. The rhodium complexes of these ligands show exceedingly high enantioselectivities (generally > 95% ee) and activities often in excess of 50 000 catalyst turnovers per hour for the asymmetric hydrogenation of a wide variety of dehydro-α-amino acid and itaconic acid derivatives. They also show high activity and good to excellent enantioselectivity for the hydrogenation of a number of α-ketoesters.

Preparation of (R)-(-)- and (S)-(+)-3-hydroxymethyl-1-tetralone tosylates, key intermediates in the synthesis of new CNS drugs, via resolution of precursors

The preparation of (R)-(-)- and (S)-(+)-3-hydroxymethyl-1-tetralone tosylates, key intermediates in the synthesis of new CNS drugs in the aminobutyrophenone family, has been developed via classical resolutions or lipase-catalyzed kinetic resolution of one of their precursors.

Phosphinoferrocenylaminophosphines as novel and practical ligands for asymmetric catalysis

(Matrix Presented) A new series of ligands with a novel phosphine-aminophosphine ligation design as depicted in structure 1 has been prepared on a ferrocenylethyl backbone. These BoPhoz ligands of structure 2 have afforded exceedingly high activity and enantioselectivity in the rhodium-catalyzed asymmetric hydrogenation of dehydro-α-amino acid derivatives, itaconic acids, and α-ketoesters. These air-stable ligands are readily prepared from cost-effective and non-pyrophoric intermediates.

Synthetic study of AAL-toxins: Efficient construction of two vicinal diol moieties by asymmetric dihydroxylation

Asymmetric dihydroxylation has been applied to syntheses of two vicinal anti-diol moieties in key intermediates of AAL-toxins. The strategy allowed efficient construction of left- and right segments of AAL-toxin main chain.