114195-57-2

Basic information

• Product Name: (2R)-diethyl 2-methylsuccinate
• CAS NO: 114195-57-2
• Molecular Weight: 188.224
• Mol File: 114195-57-2.mol

Chemical Properties

• CAS DataBase Reference: (2R)-diethyl 2-methylsuccinate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-diethyl 2-methylsuccinate(114195-57-2)
• EPA Substance Registry System: (2R)-diethyl 2-methylsuccinate(114195-57-2)

Safety Data

• Hazardous Substances Data: 114195-57-2(Hazardous Substances Data)

Upstream product

• 2418-31-7 (E)-2-methyl-but-2-enedioic acid diethyl ester 
• 2409-52-1 diethylitaconate 
• 498-23-7 citraconic acid 
• 2170-03-8 itaconic acid anhydride 
• 64-17-5 ethanol 
• 83247-83-0 (R)-(+)-3-methyldihydrofuran-2,5-dione 
• 691-83-8 diethyl citraconate 
• 120569-39-3 (R)-4-((S)-4-Isopropyl-2-oxo-oxazolidin-3-yl)-3-methyl-4-oxo-butyric acid ethyl ester 

Downstream Products

• 752174-62-2 (2R,4S)-4-amino-5-biphenyl-4-yl-2-methylpentanoic acid ethyl ester 

Relevant articles and documents

Enantioselective hydrogenation of olefins by chiral iridium phosphorothioite complex covalently anchored on mesoporous silica

Chiral monodentate phosphorous-based ligands have proven effective for the enantioselective hydrogenation of olefins. Binol-derived monodentate phosphorothioite (PS) ligand was synthesized from binol and thiopropyltriethoxysilane, and its iridium complex was covalently anchored to mesoporous silica supports like SBA-15, MCM-41, and MCM-48. These catalysts were characterized by different physicochemical techniques and assessed for their catalytic performances in the heterogeneous asymmetric hydrogenation of itaconic acid and its derivatives. It was found that the catalytic activities and enantioselectivities of the heterogenized iridium complex (IrPSSBA-15) in the hydrogenation reactions were comparable to its homogeneous analogue. Binol-derived monodentate phosphorothioite ligand in heterogeneously anchored form (iridium complex) is a more effective catalyst than the reported monodentate phosphorous ligand systems in the hydrogenation reactions, possibly due to the changes in electronic properties around the iridium metal center. The effects of substrate-to-catalyst molar ratio, solvents, and temperature on substrate conversions and enantioselectivities of the products were investigated in hydrogenation reactions.

New chiral ligands bearing two N-heterocyclic carbene moieties at a dioxolane backbone. Gold, palladium and rhodium complexes as enantioselective catalysts

Biscarbene ligands with two imidazolin-2-ylidene moieties at a chiral dioxolane backbone were used as ligands for gold, rhodium and palladium complexes. All new complexes showed varying degrees of enantioselectivity toward hydrogenation of prochiral alkenes with ees up to 95%. The Royal Society of Chemistry 2010.

Preparation method and application of sacubitril intermediate

The invention discloses a preparation method and application of a sacubitril intermediate. The sacubitril intermediate disclosed by the invention is obtained by taking itaconic anhydride as a raw material, performing chiral reduction, esterification, selective hydrolysis and carboxyl activation, and finally conducting coupling with 4-biphenylacetic acid. The invention also provides a method for preparing sacubitril by using the sacubitril intermediate. The preparation method provided by the invention has the advantages of easily available raw materials, simple process, economy, environmental protection and the like, and is more suitable for industrial production compared with other routes.

Steric effects on the stereochemistry of old yellow enzyme-mediated reductions of unsaturated diesters: Flipping of the substrate within the enzyme active site induced by structural modifications

The ene-reductase-mediated reduction of the carbon-carbon double bond of some alkyl 2- substituted butenedioates was investigated. The stereochemical outcome of the reaction was found to be influenced by steric effects. Ethyl and butyl citraconates were converted into the corresponding alkyl (R)-2-methylsuccinates with excellent enantioselectivity, whereas ethyl and butyl mesaconates were completely unreactive. Methyl 2-substituted fumarates were reduced to enantiomerically enriched methyl (S)-2-substituted succinates, whereas the (Z)-stereoisomers were left unreacted by enereductases. Labelling experiments were performed to investigate the mechanism of these bioreductions and explain their stereochemical outcome.

Asymmetric bioreduction of activated carbon-carbon double bonds using Shewanella yellow enzyme (SYE-4) as novel enoate reductase

Shewanella yellow enzyme (SYE-4), a novel recombinant enoate reductase, was screened against a variety of different substrates bearing an activated double bond, such as unsaturated cyclic ketones, diesters, and substituted imides. Dimethyl- and ethyl esters of 2-methylmaleic acid were selectively reduced to (R)-configured succinic acid derivatives and various N-substituted maleimides furnished the desired (R)-products in up to >99% enantiomeric excess. Naturally occurring (+)-carvone was selectively reduced to (-)-cis- dihydrocarvone and (-)-carvone was converted to the diastereomeric product, respectively. Overall SYE-4 proved to be a useful biocatalyst for the selective reduction of activated CC double bonds and complements the pool of synthetic valuable enoate reductases.

Development of homogeneous and heterogenized rhodium(i) and palladium(ii) complexes with ligands based on a chiral proton sponge building block and their application as catalysts

Chiral compounds prepared from proton sponge building block 8-((2R,5R)-2,5-dimethylpyrrolidin-1-yl)naphthalen-1-amine were found to be effective chiral ligands for obtaining complexes of rhodium(i) and palladium(ii) by reaction with [RhCl(cod)]2, PdCl2(cod) or Pd(OAc) 2. The complexes bearing triethoxysilane groups were immobilized on mesoporous MCM-41 in order to obtain new heterogeneous catalysts. Both materials are active in the hydrogenation of alkenes and could be recycled without loss of activity or enantioselectivity.

Synthesis of electron-rich CNN-pincer complexes, with N-heterocyclic carbene and (S)-proline moieties and application to asymmetric hydrogenation

New chiral CNN-pincer-type gold, palladium, and rhodium complexes containing N-heterocyclic carbene substituent and (S)-N-tert-butyl- methylpyrrolidine-2-carboxamide as chiral auxiliary have been synthesized and studied for asymmetric hydrogenation. The complexes were prepared by the silver carbene transfer route from the respective silver complex. The reaction with [RhCl(cod)]2 (cod = cycloocta-l,5-diene), PdCl2(CH 3CN)2, or K[AuCl4] affords the corresponding cationic [Rh(cod)(ligand)]Cl, [PdCl(ligand)]Cl, and [AuCl(ligand)]Cl2 complexes in which the ligand functions effectively in a CNN coordination mode. The complexes catalyze the enantioselective hydrogenation of prochiral alkenes. Enantioselectivity is very sensitive to the NHC N-substituent, resulting in a useful switch in the predominant enantiomer.

Immobilization of (NHC)NN-pincer complexes on mesoporous MCM-41 support

Unsymmetrical pincer-type-ligated {pincer = [C6H 3N(CH2L1)(CH2L2)-2,6], L1 = prolinamide, L2 = NHC} gold and rhodium complexes have proven to be highly effective catalysts for the hydrogenation of alkenes. Immobilization on ordered mesoporous silica (MCM-41) using a grafting process offers significant potential advantages in the application of such catalysts particularly with respect to catalyst separation and recycling. We describe one approach toward such immobilization: covalent bonding to silica via a pendant alkoxysilane group. This approach yields catalysts that are robust, recyclable, and comparable to or even more active than the corresponding species in solution. Spectroscopic evidence (IR spectroscopy, solid-state CP/MAS NMR, SEM), elemental analysis, and studies of catalytic activity support the hypothesis that binding occurs at the prolinamide substituent with no complex degradation. Control experiments showed the true heterogeneous nature of the catalyst in this reaction. Analyses of the hybrid materials revealed that the mesoporous structure of these materials was retained during the immobilization process as well as during catalysis.

OPTICALLY ACTIVE α-ALKYLSUCCINATES FROM THE STEREOSELECTIVE ALKYLATION OF CHIRAL IMIDE ENOLATES.

The chiral oxazolidinones 1 and 2 were alkylated by methyl bromoacetate, then subsequent removal of the chiral auxiliary provided readily with high stereoselectivity the α-alkylated succinates 7 and 8.Acyloin condensation and bromination gave the optically active α-t-butylcyclobutanedione 10.