39910-24-2

Upstream product

• 141-97-9 ethyl acetoacetate 
• 123-11-5 4-methoxy-benzaldehyde 
• 17145-48-1 ethyl 2-diazo-2-(trimethylsilyl)acetate 
• 623-73-4 diazoacetic acid ethyl ester 

Downstream Products

• 239094-48-5 C₂₀H₂₁N₃O₇S 
• 811467-26-2 3-hydroxy-3-(4-methoxy-phenyl)-2-oxo-propionic acid ethyl ester 
• 1073163-35-5 ethyl 2-diazo-3-(4-methoxyphenyl)-3-oxopropanoate 

Relevant academic research and scientific papers

A Conjugate Addition Approach to Diazo-Containing Scaffolds with β Quaternary Centers

Structurally complex diazo-containing scaffolds are formed by conjugate addition to vinyl diazonium salts. The electrophile, a little studied α-diazonium-α,β-unsaturated carbonyl compound, is formed at low temperature under mild conditions by treating β-h

Highly efficient and chemoselective direct aldol reaction of acyldiazomethane with aldehydes promoted by MgI2 etherate

Direct aldol condensation of various aromatic, heteroaromatic, α,β-unsaturated aldehydes and aliphatic aldehydes with acyldiazomethane was realized using MgI2 etherate (MgI2·(Et2O)n) as a promoter in the presence of diisopropyl amine (DIPEA) in excellent yields in a short time under mild conditions with high chemoselectivity. Iodide counterion, and a non-coordinating less ploar reaction media (i.e., CH2Cl2) are among the critical factors for this unique reactivity.

An efficient and convenient aldol addition of acyldiazomethane with aldehydes promoted by MgI2 etherate

The aldol addition of acyldiazomethane with aromatic aldehydes, vinyl aldehyde and aliphatic aldehydes was carried out efficiently in the presence of MgI2 etherate and iPr2EtN (DIPEA) using untreated reagent-grade CH2Cl2 under atmospheric conditions in good to excellent yields. Iodide counterion and a non-coordinating reaction media (i.e. CH2Cl2) are among the critical factors for the unique reactivity of this reaction system.

Deep eutectic solvent (DES) as dual solvent/catalyst for synthesis of α-diazocarbonyl compounds using aldol-type coupling

Deep eutectic solvent (DES) was employed as dual solvent/catalyst in the green synthesis of α-diazocarbonyl compounds using aldol-type coupling. α-Diazocarbonyl compounds are important synthetic intermediates with useful application for synthesis of amino alcohols and acids and many natural products. Moreover, the method is environmentally friendly because of avoidance of toxic solvents or hazardous catalysts.

KF/Nano-clinoptilolite Catalyzed Aldol-Type Reaction of Aldehydes with Ethyl Diazoacetate

Abstract: Potassium fluoride supported on nano-clinoptilolite (KF/CP NPs) was used as an excellent catalytic system for direct aldol-type condensation of aldehydes with ethyl diazoacetate under solvent-less conditions. A variety of α-diazo carbonyl derivatives were prepared in good to excellent yields in short reaction times. Graphical Abstract: [Figure not available: see fulltext.]

An efficient aldol-type reaction of ethyl diazoacetate with aldehydes promoted by MgI2 etherate

The first example of the preparation of α-diazo-β-hydroxy esters by the aldol-type condensation of aldehydes with ethyl diazoacetate using Et3N as base in the presence of magnesium iodide etherate [MgI2.(Et2O)n] has been achieved in good to excellent yields at room temperature in CH2Cl2 in 15-30 min.

Continuous flow synthesis of toxic ethyl diazoacetate for utilization in an integrated microfluidic system

An integrated microfluidic system for multiple reactions and separations of hazardous ethyl diazoacetate is presented. The integrated techniques include: a droplet technique for liquid-liquid and/or gas-liquid separation and in situ generation of the toxic reagent, a dual channel membrane technique based on a cheap polymeric microseparator for liquid-liquid separation, and a capillary microreactor for carrying out cascade reactions in a sequential and continuous manner.

Rh2(OAc)4-catalyzed 2,3-migration of β-ferrocenecarboxyl α-diazocarbonyl compounds: An efficient synthesis of ferrocene-containing α,β-unsaturated esters

A series of β-ferrocenecarboxyl α-diazocarbonyl compounds were prepared by the reaction of ferrocenoyl chloride with β-hydroxyl α-diazocarbonyl compounds in the presence of pyridine. The diazo decomposition of these ferrocene-containing diazocarbonyl compounds with Rh 2(OAc)4 resulted in 2,3-ferrocenecarboxyl migration to give ferrocene-containing α,β-unsaturated esters in high yields.

Tert-BuOK-Catalyzed condensation of ethyl diazoacetate to aldehydes and palladium-catalyzed 1,2-hydrogen migration for the synthesis of β-ketoesters under solvent-free conditions

A mild and convenient method for the condensation of ethyl diazoacetate (EDA) with aldehydes catalyzed by tert-BuOK under solvent-free conditions was developed. The corresponding α-diazo-β-hydroxy esters were further converted into β-ketoesters through palladium-catalyzed 1,2-hydrogen migration under neat conditions. The two-step transformation exemplifies a simple method for the efficient and green synthesis of β-ketoesters. The Royal Society of Chemistry 2013.

Development of the enantioselective addition of ethyl diazoacetate to aldehydes: Asymmetric synthesis of 1,2-diols

A novel synthetic strategy toward the asymmetric synthesis of vicinal diols bearing a tertiary center is presented. The method encompasses the dinuclear Mg-catalyzed asymmetric addition of ethyl diazoacetate into several aldehydes, oxidation of the diazo functionality, and diastereoselective alkyl transfer of various organometallics into the resulting chiral β-hydroxy-α- ketoesters to afford a diverse range of 1,2-diols in high yield, diastereoselectivity, and chirality transfer.