73178-43-5

Upstream product

• 32328-03-3 diethyl 3-hydroxyglutarate 
• 18852-51-2 sodium cyanoacetic acid ethyl ester 
• 64-17-5 ethanol 
• 1724-02-3 glutaconic acid 
• 96-23-1 1,3-Dichloro-2-propanol 
• 151-50-8 potassium cyanide 
• 91967-12-3 ethyl 3-acetoxypentanedioate 
• 623-73-4 diazoacetic acid ethyl ester 
• 140-88-5 ethyl acrylate 
• 20357-65-7 6-chloro-2H-pyran-2-one 
• 14369-81-4 ethyl 2,3-butadienoate 
• 201230-82-2 carbon monoxide 
• 628-48-8 glutaconic acid 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 

Downstream Products

• 27847-33-2 4-phenylhydrazono-pentenedioic acid 
• 51865-85-1 1,3-diethyl 2-aminoglutarate 
• 90722-08-0 3-bromo-glutaric acid diethyl ester 
• 69134-53-8 (+/-)-diethyl 2-hydroxypentandioate 
• 119507-22-1 1,3-diethyl 2-benzylaminoglutarate 
• 184921-34-4 4-Ethoxycarbonylmethyl-1H-pyrrole-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Ligand-Controlled Palladium-Catalyzed Alkoxycarbonylation of Allenes: Regioselective Synthesis of α,β- and β,γ-Unsaturated Esters

The palladium-catalyzed regioselective alkoxycarbonylation of allenes with aliphatic alcohols allows to produce synthetically useful α,β- and β,γ-unsaturated esters in good yields. Efficient selectivity control is achieved in the presence of appropriate ligands. Using Xantphos as the ligand, β,γ-unsaturated esters are produced selectively in good yields. In contrast, the corresponding α,β-unsaturated esters are obtained with high regioselectivity in the presence of PPh2Py as the ligand. Preliminary mechanistic studies revealed that these two catalytic processes proceed by different reaction pathways. In addition, this novel protocol was successfully applied to convert an industrially available bulk chemical, 1,2-butadiene, into dimethyl adipate, which is a valuable feedstock for polymer and plasticizer syntheses, with high yield and TON (turnover number).

Organocatalytic asymmetric formal [3 + 2] cycloaddition with in situ-generated N-carbamoyl nitrones

(Chemical Equation Presented) A novel organocatalytic formal [3 + 2] cycloaddition reaction with in situ generation of N-carbamoyl nitrones is presented. For the first time, N-Boc- and N-Cbz-protected isoxazolidines have been directly obtained as single diastereoisomers in generally high yields and enantiomeric excesses using mild reaction conditions and inexpensive, readily available Cinchona alkaloid quaternary ammonium salts as catalysts. Synthetic manipulations of the products provided highly valuable building blocks such as free isoxazolidines, a N-Boc-1,3-aminoalcohol, and a free δ-lactam. This report represents a pioneering work in the use of N-carbamoyl nitrones as electron-poor 1,3-dipoles and glutaconates as new dipolarophiles in asymmetric catalysis.

NOVEL CHROMEN-2-ONE BASED HYDROXAMIC ACID DERIVATIVES HAVING ANTI-INFLAMMATORY ACTIVITY, THE PREPARATION THEREOF AND A COMPOSITION CONTAINING THE SAME FOR TREATING INFLAMMATORY DISEASE

The present invention relates to novel chromen-2-one based hydroxamic acid derivatives having anti-inflammatory activity, the preparation thereof and a composition containing the same for treating inflammatory disease.

Halogenated-2-pyrones in Sonogashira cross-coupling: limitations, optimisation and consequences for GC analysis of Pd-mediated reactions

The Sonogashira couplings of 4-bromo-6-methyl-2-pyrone (5) with phenylacetylene, mediated by Pd(PPh3)2Cl2 in the presence of a CuI co-catalyst, have been investigated in detail. The concentration of Pd dramatically influences the product yield, with lower Pd-loadings favouring higher conversions and purer cross-coupled product. A post reaction time-dependence in product conversion is seen in samples quenched solely on silica-gel (eluted with CH2Cl2). The effect is mirrored in reactions employing 4-nitro-bromobenzene (14) and to a lesser extent (E) and (Z)-ethyl 3-iodo-2-propenonate (16) under similar conditions. A more efficient quenching system (using excess dppe) has been developed to enable accurate determinations in product conversions. Alternatively, solvent and base (Et3N) removal in vacuo, or quench with saturated aqueous ammonium chloride, prevents further turnover in Sonogashira coupling. An ESI-MS study on samples eluted through silica was undertaken to probe the nature of the soluble Pd/Cu species. The Sonogashira cross-coupling of 4-chloro- and 6-chloro-2-pyrone (18 and 20, respectively) has further been investigated. The former undergoes successful coupling, however the latter decomposes in polar aprotic and protic solvents under standard conditions, through a chlorine substitution process, making Pd-mediated reactions problematic.

Molybdenum Hexacarbonyl Catalyzed Cyclopropanation of α,β-Unsaturated Esters and Nitriles with Diazocarbonyl Compounds

Molybdenum hexacarbonyl, when employed in catalytic amounts, effectively promotes cyclopropanation of acrylonitrile, methacrylonitrile, and ethyl acrylate by ethyl diazoacetate and α-diazoacetophenone; the intermediacy of molybdenum carbene species in the formation of cyclopropane derivatives is suggested.